#292: Wealth (& massive insecurity) is messing up my love life.

still frame from Disney's Beauty and the Beast
This is a sweet story about a man who had both self-loathing and wealth who coerced a young woman into living with him until such time she could develop Stockholm Syndrome and consent to marriage.

Hello Captain Awkward,

I have an issue that you probably don’t get every day. I have a problem with wealth and dating. I’m in my late 20’s, and I have had the good fortune of becoming quite wealthy. Unfortunately, I am having trouble finding women who like me for me and not my wealth. Back when I was a poor student, I never thought this would be an issue, but it is. I believed that money would solve all my problems with being awkward and feeling inferior and not being able to get laid, and it did help with a lot of those things. It has made finding actual love and good relationships much more difficult. I don’t fit in with the dynastic wealth crowd, and I know there are tons of great women who grew up with money and are not in any way impressed by mine, but I just don’t fit in with that group of people. I have been trying to figure out how to navigate this issue, and it just blew up in my face.

I was seeing a woman for 3 months, but I was lying about my wealth. I have a small apartment in the same building as my real apartment, so I can try to get to know women without getting entangled with the ones who are just with me for my money. It is the sort of apartment that says, “I’m doing well, but I’m no rich guy.” Last week, I decided to come clean, and it did not end well. It was the first time where we went out and I was living life as I live it when I’m not worried about what people are going to think about my money. She thought it was this special occasion because everything was stepped up considerably from our usual dates. I tried explaining that really, I was maybe not being so honest about my income, which she didn’t believe until we came back to my actual apartment. She was furious, and I can understand it. She went on at length about my deception, not trusting her, and treating her like a potential gold digger.

It is true, but I don’t know what else to do. She won’t talk to me, and I think our relationship is probably over. How can I find people who like me for me while living a lifestyle that clearly shows how wealthy I am? I have been burned before both with friends and girlfriends who I thought liked me for who I am but turned out to be interested in being close to someone who is doing well. I have reined in my conspicuous consumption a lot in the past year and a half, but I like having a very nice apartment, I like dressing well, and I like having a nice car. I feel terrible about feeling sorry for myself because this is a problem almost everyone would be envious to have, but I am very lonely.


A Good Problem Is Still a Problem

Dear Good Problem:

Here are the problems I see in your letter that get in the way of dating success.

1) You are massively insecure. The wealth didn’t make you less so, it just made it manifest differently. Paranoia that people won’t like you has turned into paranoia that people only like you for your money. You just built yourself a slightly nicer “don’t get close to people” prison than you had before.

2) You are a big lying liar who *has a second fake apartment* you use for dating purposes. I don’t know what kind of big fairy tale moment you were expecting when that nice woman you were dating saw your real apartment but I’m not surprised that she found that all the money in the world couldn’t make up for the contempt that you showed her when you lied to her that way. Do you see how fucked up and controlling it is to give people secret tests like that? “Spin this straw into gold and then you can marry the king!

It’s time for some therapy to figure out the source of your insecurities, massive trust issues, and find a way to turn off those tapes that play over and over in your head.

And it’s time to do some work on yourself and your self-confidence. What makes you interesting? What makes you worth knowing? What are you passionate about? What makes you a good time to be around? What makes you a worthwhile friend and lover? How are you spending that money of yours to make the world a better place or to make a really interesting life for yourself? (Nice clothes, cars, space = nice, but after 15 minutes anyone worth knowing is going to be like ok, what else have you got going on?) Do you have a real talent and passion for your work? What is it about the work that makes you want to do it?

You need to be really nice to yourself about this and learn to be okay with you. Who would you be if you didn’t have any money? What’s awesome about that guy? Get back in touch with that person and trust that he’s cool enough to be loved. Here are some steps for maybe liking yourself better:

Step 1: Find a therapist. You may not find the right fit at first, so be prepared to change it up after a few sessions if you aren’t connecting.

Step 2: Explore some passion or curiosity or dream that you have. Even if you’re bad at it at first and there is a steep learning curve. Bonus if it’s the kind of thing that brings you into regular contact with other people.

Step 3: NO MORE LYING. It’s definitely ok to keep early dates chill, inexpensive, and casual while you’re just getting to know someone. It’s definitely ok to let your dating partners split or pick up the check from time to time and take the lead in looking for ways to make you happy. And it’s okay to take them somewhere swanky if you think you’ll both enjoy it. Early stages of dating are all about figuring out how you feel and looking for reciprocity and signs of caring and trust in the other person. It should feel like a dance where no one in particular is leading, not a project.

I can see that it’s maybe easy to overwhelm the other person with things that they can’t easily pay back or tempting to swoop in as Problem Solving Guy or show off with fancy dinners, but the best things that our partners do for us don’t really cost money. “I’m feeling crappy. Bring me soup and sit and hold my hand and watch movies with me.” “Do silly dances while you make breakfast and make me laugh.” “Stay up all night and tell me about your dreams.

The biggest thing for me is to feel like my partner pays attention. He asks me how my day went. He remembers when I’ve got something important going on and wishes me luck beforehand and asks me how it went afterward. He pays attention to things I like to eat & read, etc. and surprises me with them when he can. He lets me know things he likes and gives me the opportunity to return the favor. He introduces me to his people and makes the effort to meet and get to know mine. He tells me honestly what’s on his mind, even if it’s messy and vulnerable, and doesn’t try to present some picture-perfect facade. This frees me to do the same. We seek out, support, and encourage each other’s creative efforts. None of this costs money – we don’t have any.

You have to find a way to like yourself better and trust that your time and attention are enough for the right person. I don’t know exactly how you get there, but right now your frame is “I might not be so great, but I have money! Let me trick someone into liking the not-so-great me and then they’ll be rewarded with money!” A year from now I want your frame to be “I’m awesome. Yeah, that’s money. Who cares? Let’s do awesome stuff!

Step 4: Put as much love as you can into your family, friendships, and wider community. Surround yourself with people who love you and who you love. Invite them in, spend time with them, listen to them, feed them, ask them for help when you need it, let them care for and feed you (both with actual food and comfort and love). Be a great boss, a great coworker, a great guy who goes and walks and plays with dogs at the animal shelter or reads to old people, a great son, a great brother, a great friend. You’ll feel less vulnerable & lonely in dating if you feel less lonely in general.

Finally, if you do end up chasing after your most recent Cinderella as she flees the ball, here’s what an apology looks like:

I’m truly sorry. I should have trusted you and not tried to control how you perceived me. That was massively messed up and you did not deserve it.”

Leave out the part where people have screwed you over in the past or anything where you feel totally justified because: gold diggers, and don’t try to make her feel sorry for you or win her back. You’ll feel better for making a sincere apology that doesn’t ask for anything in return.

189 thoughts on “#292: Wealth (& massive insecurity) is messing up my love life.

  1. I loved your reply – it cut through all the excuses and really got to the heart of LW’s issues. Thanks Captain, this is just why I read you. 🙂

  2. Wow, this does not answer the question at all. I completely agree with you that Good Problem needs a reality check, some self-esteem, and to stop lying to people.

    However, I think you miss the real, genuine problems money can create, maybe because, as you say, you don’t have a lot? Which is fine, but let’s not pretend it makes no difference. As much as lying is not the way to get around the problem, it is genuinely difficult to have normal relationships (dating or otherwise) across a vast wealth gap. When I want to bring a fancy dessert to a chronically-broke friend’s house as a treat for her–not a big deal, but something I hope will make her day brighter, not something I’m using to try to buy her friendship or show off or whatever–I have to decide whether the enjoyment of the dessert will be worth the resentment she may feel for me. Will she just think I’m rubbing it in her face that I can afford this kind of thing and she can’t? If I want to go out to a moderately-priced meal with friends, I have to think about whether it may be a super-expensive meal for them, and whether, therefore, it is worth doing for no particular occasion, or whether I should save that kind of thing for big occasions. And then what about me–if I want to go out for a really special occasion for me, I can’t, unless I want to go alone, since most of my friends and dates are less well off than I am, because offering to pay might be regarded, again, as showing off or whatever rather than just as “Hey, I would like to do this thing and I would like you to do it with me, so let me make that happen.”

    Now, having money is great and I’m grateful for it. I don’t want to sound like I’m not. But I wish you hadn’t thrown it back in Good Problem’s face as if his ONLY problem is that he is insecure and tells lies to cover for it.

    1. I would love to hear more about this from people with money, because I agree that it can be an issue that needs to be negotiated and requires some boundary-setting, but you sound kind of paranoid and insecure yourself if the idea of bringing dessert to a friend can open up the fear that you’re rubbing something in her face or buying her friendship or incurring resentment instead of just doing something nice and enjoying each other’s company. I’m reading all kinds of fear and shame in your letter that is similar to the LW’s.

      I think it’s very considerate for you to think about whether a night out at a certain kind of restaurant is a splurge for your friends, but what would happen if you took them at their word when they wanted to come with you to the nice one, or gave them a few options across the cost spectrum and let them pick their comfort zone? And I think it’s very considerate for you to try to frame things in a “I want to go do this awesome thing, can I treat you? I’d love your company,” way and consider your friends’ pride and try to remove anxiety. Several years ago I was the fortunate recipient of a very nice trip to Paris with just such strings attached: “Please come & have a great time with us,” and my advice to the poorer friends is “When your friends want to treat you, take them at their word and don’t make a big thing out of it, trust your mutual affection, and find non-financial ways to reciprocate.”

      Being gracious about accepting favors is something that most of us, with our stupid pride, have to learn at some point or another. A nice friend who treats you to things is a “good problem” kind of way to learn about this skill, and if someone is responding to a nice favor or gesture with resentment or complaining at length about their own finances then they are behaving badly. Reciprocity doesn’t have to exactly balance out, favor for favor, dollar for dollar, eye for eye. It’s a feeling that something is mutually enjoyable and both parties are interested in contributing what they can.

      I don’t want to say your problems (or the LW’s) aren’t real, and I’m not under the illusion that money creates no tension and that people who expect to be bailed out, ask for favors, act resentful, etc. don’t exist. There’s such a cultural taboo around discussing money that I can see why it feels “easier” to seek out people of similar economic status, but that’s so sad and feels like giving up. I definitely think shame is harmful to both sides – shame of being too poor and needing favors, shame of being wealthy and fearing resentment or being taken advantage of – and the way to get past shame is work on getting more comfortable with yourself and more honest and comfortable and vulnerable in relationships. And to take people at their word and let their resentments be their own, not something you caused.

      1. “I definitely think shame is harmful to both sides – shame of being too poor and needing favors, shame of being wealthy and fearing resentment or being taken advantage of”

        When I was a part-time student, my roommate and his sister used to treat me to stuff all the time. Drinks, meals, movie tickets – they knew I couldn’t afford to do that stuff as often as the rest of the group, but they wanted me along, so they ponied up. One day I felt particularly embarrassed thinking about how much they must have spent on me over the months, and I was all ‘I swear when I’m qualified and earning good money I’ll treat you back’, and Roommate’s Sister said the coolest thing:

        ‘Don’t pay it back to us. We don’t need it back. When you’re done with school and you’ve got money, you’ll have other friends who don’t – pay it forward to them instead.’

        These days I’m a qualified accountant, and I have friends who are students and/or unemployed, so I often treat them so we can do cool stuff together. And if they say anything about paying me back one day, I tell them about what Roommate’s Sister said, and tell them that they’ll pay it forward one day, too.

        1. There is no thumbs up button here, and so I will just leave this comment to say: Word.

        2. This is what my friends did for me, in my final years at university. I had almost no disposable income – and was totally happy hanging out at home on the cheap – but when they wanted to do costly stuff, sometimes they’d cover for me. (My good friend once told me ‘I like having your company much more than I like having my money.) Now I am earning, I like to be able to pay it forward.

          Finally, LW, I have good news for you. There are lots and LOTS of women who like taking care of themselves. Eg. I routinely split checks – I don’t like to feel there is a debt either way. The answer has to be somewhere along the lines of… only do what you feel comfortable doing. Don’t hand over a creditcard to a date, or take them somewhere because you feel obligated as a “rich guy”. It’s the same as when people think taking care of some guy obligates him to stay. Do what you want – and then their reaction won’t hurt you so much.

          P.s. Date feminists. A true feminist can talk with you about how all kinds of power imbalances in relationships – your thing is just one of the many. Best of luck.

      2. So I’m not sure how many zeroes it takes to have “dynastic wealth,” though however many it is, I don’t qualify, but I am very fortunate. And I think your advice is exactly correct — trust that if a friend offers something, take them at their word that they want to do that for you because they like you. (And if you have money, offer it truly in the spirit of wanting to be kind and share with your friend, with zero expectations that it will be repaid financially, but rather in their enjoyment.)

        1. I’m pretty sure dynastic wealth just means inherited wealth, not a specific amount.

          1. I know, but I meant how much money to be part of a set of people for whom inheriting wealth is a defining characteristic. How much money makes a dynasty, basically. (It was mostly a pretty dumb joke.)

          2. Ah, got it, Allison. That whole pesky tone/text thing. (This reply should be nested one more.)

      3. Exactly, exactly this. Not to sound crass, but if you do something genuinely nice and thoughtful for a friend with no arrogance or manipulation behind it, someone with whom you have a happy, comfortable relationship should be grateful. If they descend into “poor me” guilt, that’s either a reflection on them having some issues to work through that have basically nothing to do with you, or a reflection on your ability to really, genuinely give to people with no strings attached.

        1. I don’t think it’s that simple at all. I had a friend who used to treat me to things and insisted it wasn’t a big deal, and after YEARS of friendship, I stood up for my opinion when I disagreed with her, and she threw every nice thing she had ever done for me in my face. Add that to my upbringing, where I learned that every gift and favor had strings attached, and I am VERY nervous about those kinds of things, even from dear and trusted friends. That deep and visceral a reaction is not easy to dismantle. I’ve been in therapy for years, and I still have it.

          Part of it is a general reinforcing cultural narrative that material expressions of care are superior to nonmaterial expressions of care, and require material reciprocation. The other is the lie that reciprocation isn’t necessary. It is TOTALLY necessary in every relationship, and to pretend that it isn’t is disingenuous as best. We need to just expand the categories for what is considered reciprocation, is all. Kate Griffiths’s example is a great one – when I lived in South Korea, this was the general cultural philosophy, and I got really comfortable accepting that most older people would pay for me, and I would pay for most people younger than me (expats always split checks, and again, I had reciprocity issues with letting them treat me). It was explicitly laid out that way. Lately, I’ve discovered that baking or cooking for people is a good way for me to feel like I am contributing equally (yaaaay foodstamps). I also help keep a friend’s house clean, because I spend the night there a lot and often end up cooking (adding effort!) and eating my friend’s food when I do.

          But generally, to say that people SHOULD be okay with something because of their friends’ intentions is to ignore that 1. people are different, and 2. intent is not magic. You can’t make someone feel comfortable by wanting them to feel comfortable, and having a relationship across ANY gap, including a wealth one, requires a good understanding and some compromise from BOTH people.

          1. Intent isn’t magic, no, but my point was that if you do something that is genuinely nice and giving for someone else without strings attached and they handle it badly, it’s a reflection on *their* issues and not you. That doesn’t mean you should keep doing it once you know that it makes someone uncomfortable or creates problems, because that’s a yucky overstepping of boundaries, but that it doesn’t mean that bringing your friend a cake or something is *bad*. People can have all sorts of difficulties with accepting kindness for all sorts of reasons, and I’m not immune to this myself, but that’s a reflection on *my issues* and not on whoever is trying to do something nice for me.

            That said, we’re talking about the “bringing a cake to a friend who is having a bad week” or treating for dinner or something kind of nice things, not crazy over the top “let me unexpectedly and without asking you first buy you tickets for a month long round the world vacation” kind of nice things.

      4. I think learning to accept the generosity of others with no strings from either side really could be a post of its own, too. This was SUCH a struggle for me when I was a young whippersnapper, because I just didn’t have the life experience or the socialization (I was practically a feral child :D) to deal with it. I had quite a bit of anxiety when friends had to pick up my tab because I had a huge amount of anxiety in general about how poor I was. (Okay, am. :D) I didn’t get over it until I realized that I had exactly zero concerns about the times I was paying for someone else. If it wasn’t a burden in the slightest for me to pick up the lunch tab once in awhile, why did I think others would resent treating me every now and again? Luckily I’ve been graced with some very patient and very kind friends, and over the years I’ve very often been in the position to treat others or to need to be treated, and it’s honestly become one of the great joys of my life. I LOVE being able to afford to treat a friend to dinner or something, and I LOVE when I’m flat broke and a friend offers to treat me, because in both situations the common denominator is that I’m spending time with my friend.

        I can see how a big earning disparity could turn into some awkward social decisions, but the most important thing in any relationship is that you’re enjoying one another, thinking of each other’s comfort and enjoyment, and spending time together.

      5. On the general front of a wealthier person’s process of dealing with income disparities in relationships, I think that there’s a greater responsibility to try to be sensitive to the possibility of discomfiting people in new relationships. Income disparities are awkward, and can bring out all kinds of issues, and as the ones with the privilege, I do think that it’s important that wealthier folks make some extra effort to be tactful in how they frame offers to treat friends or the like. I’ve been on both sides of this one, and it’s a lot easier to make an offer with greater care than to deal with one that has been made in a way that feels degrading or like a string-trap.

      6. “I would love to hear more about this from people with money”
        “I’m reading all kinds of fear and shame in your letter that is similar to the LW’s.”

        Incoming wall of text, my apologies.
        I grew up in a rather wealthy family, and I think you’re spot-on in mentioning that there’s a lot of fear and shame attached to money if most of your friends don’t have it. I know as far as problems go, being rich is basically the best problem you can have, and it’s awful to complain about it and you look like a whiny jerk to everyone who’s struggling to make ends meet. But there’s no denying that it can cause some really weird interpersonal issues.

        Captain, you are the awesomest and I love you completely to bits, but I really want to offer a little bit of constructive criticism. I love love love your advice in step 3 especially. That is great advice. But as someone who’s dealt with some of the stuff the LW is worried about, I just wanted to mention a couple things about the rest of your advice. I tend to agree with Kate that you focused a little too much on his insecurities.

        Yes, the LW seems to have some serious insecurities and stuff he should probably work on. And yes, weird life changes will amplify existing problems. But there’s also a whole set of new problems that come along with the money. It’s taken my my whole life (in fairness, I’m still very young) to learn how to navigate the interpersonal problems that come from being richer than all my friends and richer than anyone I date. And after 20+ years I’m still not that good at it, and I still have difficulties every day. So this is a VERY new set of very real problems for the LW and he hasn’t had the experience I did of growing up rich to help him slowly learn how to deal with that. It’s going to be tough to figure it out. And it’s the sort of thing that’s hard to ask for help about. “Hi, I’m having a hard time adjusting to being rich. Do you have any advice on how I can be more comfortable with my giant piles of money?” People have very little sympathy for that, and often rightfully so.

        I think he did some totally shitty things by lying and having a fake apartment, but I also think that was less “being a big lying liar” and more “being faced with a brand-new situation you’ve never ever dealt with before, and handling it very badly.” I’m glad you were clear about what he did wrong, but I also think he deserves a little more acknowledgement of how real these problems are and how hard he’s going to have to work to get used to this brand-new set of social rules. I think he can definitely do it, and hopefully he won’t be a jerk and lie again. But it’s going to be hard to adjust to the money, and we shouldn’t demean the growth he’s going to have to go through and the hurdles he might trip over.

        1. Of course, then I read through the rest of the comments and discover what I had to say is not that original. Read through ALL the comments first, Ariel, ALL the comments. Anyways, I still feel about the same, but sorry for the overall tone of “What I have to say is new and interesting and relevant!” when other people have already said very similar things. Whoops!

        2. Appreciate the perspective and the constructive criticism. Can you off the LW some constructive advice on how to handle some of these challenges?

      7. I am certainly nowhere near as rich as the LW, but I have had the experience of a very close (non-romantic) relationship which included a large wealth disparity. It has made me uncomfortable at times both helping my friend, as well as being her confidant. It strained our friendship at times, especially since she went through breakups with two significant others, both of whom were essentially from the same financial background as me.

        The most useful thing that I learned was how far honesty will go, even if it is saying “I’m sorry, I don’t feel like I can help you as much as I should with this because I literally cannot comprehend the situation. I can still listen if you think that would help”

        This turned out to be the most useful skill that I have ever picked up since it can apply to any kind of privilege.

        1. Ha, thanks for saying what I maybe should have told the LW so clearly:

          ““I’m sorry, I don’t feel like I can help you as much as I should with this because I literally cannot comprehend the situation. I can still listen if you think that would help””

      8. You wrote the most awesomest thank you letter after that trip. That meant a lot to me.

    2. But I wish you hadn’t thrown it back in Good Problem’s face as if his ONLY problem is that he is insecure and tells lies to cover for it.
      But… it is. I’m not saying a wealth discrepancy can’t be an issue, but it’s not a more insurmountable issue than any other kind of background difference between two people. New relationships and money can be weird, no question, but having a fake apartment is not the right way to handle that. Honestly, if I’d been dating a dude for a bit and he told me that he had lied about how much money he had and had a FAKE APARTMENT to make that lie more believable, I’d assume I was being punked, or he was a serial killer. That’s a really extravagant lie, and I agree with the Captain that I hope he sees someone to help him work through the issues that caused him to feel like going to those lengths was necessary.

      1. Yeah, and…probably the second one, no offense to the letter writer. It sounds like something out of a movie. It’s a very elaborate lie, even if you could totally just rent an apartment the way someone else might buy an Almond Joy, and it speaks to an obsession with the effect of wealth.

      2. I mean, having a fake apartment is, to someone without that much money, a TERRIBLE waste of income. So spending money on a fake apartment is getting really invested in the lie and the waste makes it feel worse. If I were the LW’s girlfriend, I would ask if you couldn’t be doing something better with that money than using it to deceive me. I mean, it doesn’t have to be charity – investments, furniture, books, anything other than a massive financial investment in creating a fake persona.

        1. Exactly! If I had been LW’s date and he brought me up to his real apartment for the Big Reveal, even if my reaction to the lie was “Okay, that was really wrong and hurtful and misguided, but I can forgive you,” my reaction to Fake Apartment itself would be “This is insane and incomprehensible to me, and I don’t think I want to be with a guy who thinks this is a reasonable use of his giant piles of money.”

    3. I am fortunate to have a job that pays me what I consider to be an unreasonably large salary, and I agree with the Captain. I’ve had some situations that have felt a little awkward, where I’ve been trying to plan a dinner out or something and want to go somewhere nice but not exclude or pressure friends who don’t have as much money. But those moments don’t crop up all that often, and if you’re worrying about whether bringing a nice desert to a friend’s house will make them resent you, then there’s probably a bigger issue.

      I had the same reaction to the LW’s letter that the Captain did, because it’s such a massive overreaction to go from “some girls have dated me for my money” to “I rent a second apartment that I take girls to in order to trick them into thinking I’m not rich until they’ve stuck around long enough that I think I can trust them.” And the idea that the LW “doesn’t fit in with the dynastic wealth crowd” and just wouldn’t get along with any woman who grew up with money suggests that there are some bigger hang ups here than just having been burned by gold diggers in the past. People are individuals — people who grew up with money are not all the same, and people who didn’t are not all gold diggers. If the LW wants to meet someone who likes them for them, then the best thing to do is go do activities he or she enjoys, meet people with common interests, and stop thinking so much about how much money everyone has or might want.

      1. Another thing to think about: My friends who are better off go do stuff-I-can’t-afford all the time together without me. I read about it on FB or LJ and think “Whoa, neat! Glad you had a good time!” I don’t gnash my teeth and resent their wealth. They’re my FRIENDS. We’ll do awesome stuff together when we do awesome stuff, and there will be plenty of times when I can afford whatever it is.

        1. Captain, I just need to say that this, and your other advice on how to graciously accept help, have really made a huge difference in how I deal with money and other people. People don’t talk about money enough for me to have had any other model for how to deal with these things than the model of my parents, and it is a big relief for me to find something.

      2. It’s a good thing for people with money to think about though: how much of what we do is money-dependent? I had a group of now-ex friends who would barely spend time with me outside of restaurants, movie theaters, shopping trips, or other-money-requiring-activities. Besides my personal discomfort at having someone else pay for me, most of them weren’t well off enough to offer that, so it was time after time of “have fun, can’t go” – to the point that I felt extremely embarrassed about my poverty. When I invited them over to my home for dinner and a movie, or to a free concert in the park, or Science Pubs (YEAH OMSI), they’d say no. Not “I’m busy at that time” no, but “You live too far away (even though I have a car and you don’t, and it takes an hour for you to get here on the bus when it takes 10 minutes for me to drive there)” no, or “But we could do this expensive thing instead!” no, or whatever reason. It showed a very basic lack of understanding and respect for me, a lack of serious interest in my company, and a good deal of relative-wealthy privilege. It’s a major reason we’re not friends anymore. Reciprocity is important, beyond just matching one another’s contributions – a reciprocity of understanding, concern, care and respect for how someone feels/interacts with their financial situation.

        1. Argh, what I meant to say was: it can’t hurt anyone to try and find more things to do together that are free (or have voluntary donations (SCIENCE PUB). If you have tons of money, you can make an awesome donation to a free thing, and your friend/partner doesn’t have to feel like zie “made” you pay because you can afford to and zie can’t). It can be fun to have nights out, but it’s also great to hang out at home, cook together, play boardgames, etc.

          1. I think this is spot-on. I have some money and to be honest most of it just sits around in the bank waiting for a time when I might need it. I’m currently in a bit of a financially insecure stage of my life, in that my job (which I love) is not particularly high-paying, so I’m being careful with my savings in case of a rainy day. If I wasn’t I guess a fair amount of that money would go to charity or travelling or stuff for the people I care about or probably just sitting in the bank some more? I certainly wouldn’t suddenly start show-offishly living the good life and rubbing it in people’s faces – which to be honest, I kinda think the LW might be (perhaps unconsciously) doing? I mean if I was dating somebody and we went back to their place and they were all like “yeah, this is my super lush apartment over here, no biggie” and “yeah, I just felt like splurging on that super extravagant meal, it’s nothing to me” all fake-casual like, it wouldn’t take a FAKE APARTMENT OMG THAT IS SO MESSED UP to put me off.

          2. To be clear, I don’t think living the good life is bad if you can afford it! Just that I did get that “rubbing it in people’s faces” vibe from LW.

        2. HOW DID I JUST LEARN ABOUT SCIENCE PUBS?!? I have been varying degrees of broke and living here for like, four years. And I’ve been looking for “really good dates / hangouts” that don’t cost a lot of money for approximately forever.

    4. I think you’re in the right track, Kate, when you think about your friend’s feelings in situations like this. Maybe you don’t need to overthink things THIS much. When someone is your friend – a real friend – they\ll see acts of kindeness for what they are: awesome friends being awesome. And it doesn\’t seem like you\’ll put your friends in the kind of situation I\’ve been through once, when I spent a week complaining to a friend that I didn\’t want to spend a lot of money (we were out of town at a conference) and at the end of that week a common, very wealthy friend took us to this incredibly fancy restaurant. It was the worst meal of my life, because I spent it adding up all the prices. She never even considered that I might not be able to pay. The whole thing was made worse because the friend I had complained about money with felt bad and ofered to cover me.

      I do have other, really good friends who are well off, and whenever they want to do something more expensive-ish, I simply say: no way, I\’m broke, I\’ll skip dinner and meet you at Place X later. And it\’s all fine, really.

      1. I totally agree with your last paragraph! Sometimes when people offer to pay for things for me, they intentionally try to shame or manipulate me into agreeing – they don’t want to let me say no, and that makes me MORE uncomfortable. If you’re going to offer, you need to be okay hearing “no” as a valid and legitimate answer! Don’t pressure me! Maybe if they didn’t do that I might feel more comfortable about saying yes as well, who knows?

        1. This is something I have been learning the hard way. My significant other is currently in school, and from a poor family ( as am I). But, I’m older, have finished school, and have a job that pays me more than my mother raised 4 of us on. So, if I want to go out to eat, I treat her. But sometimes I offer to treat for something (theme park tickets, for example) and I have to be ok with hearing “no”, or it all goes wrong.

          Our deal is that I only offer what I feel good about offering, and she can always say no.

    5. i’m someone who might have ended up well-off, except for reasons. turned out, i’m on disability! i’m poor like whoa. people i know have varied incomes.

      “resentment she may feel for me. Will she just think I’m rubbing it in her face that I can afford this kind of thing and she can’t?”

      i understand that there are pride issues, but there’s trust there too. when a friend buys me something that i couldn’t afford for myself, or pays for my sushi or whatever…it’s understood. it’s a gesture of friendship, and you make that gesture because you can. it’s not some bullshit passive-aggressive power thing. it’s just friendship. before i was disabled, i sometimes paid for friends’ dinners or whatev if they were going thru a harder time, because i had money, and i didn’t mind. it was no big deal to me. (but it means a lot to the other person, as i know now that i’m the poor one)

      when a friend spends money on me in a way i can’t, i know that it’s just their way of giving. i have things to give too, but they aren’t financial.

      because i type slooowly, i checked what others have said…

      “And I think it’s very considerate for you to try to frame things in a “I want to go do this awesome thing, can I treat you? I’d love your company,” way and consider your friends’ pride and try to remove anxiety”

      that’s a rly great way to navigate the awkwardness of this sort of situation.

      “‘Don’t pay it back to us. We don’t need it back. When you’re done with school and you’ve got money, you’ll have other friends who don’t – pay it forward to them instead.’”

      this is wonderful! and a common sentiment, i think. 🙂

      other ppl have maybe said the same thing better, but hopefully this offers a bit of additional perspective.

    6. I also think that the art of gracious acceptance is something a lot of people suck at. They’re so terrified of giving the impression that they envy you, or that they are suck-ups, that they have trouble just saying “thanks, that’s lovely.”

      With your really good friends, though, you should be able to have honest conversation on the subject.

    7. Kate, you sound like a caring friend who is very sensitive to how your broke friends might feel. I’m the broke one in my friendships, and in these situations, I’d like my wealthier friends to do things in my price range.

      When you want to bring a fancy dessert, you could bring a tasty but reasonably priced dessert, like brownies from a bakery — this would cheer up your friend without making her feel uncomfortable. And when you say “if I want to go out for a really special occasion for me, I can’t, unless I want to go alone” — I thought, what’s wrong with celebrating a very special occasion at a less expensive place? If that’s what your friends can afford, why not do that for a special occasional and enjoy it? Does it really not feel special unless it’s a high-priced place?

      I think I just don’t understand because I’ve never had money, so all of my special occasions get celebrated (happily) at more casual restaurants and bars. And I would have a hard time understanding why a rich friend would push to do something expensive, and offer to pay for it — because in my (clueless broke person) mind, we can have just as much fun doing something that I can afford, so why not do that?

      But I understand that people develop habits and preferences in their price range, and that’s normal to an extent. I can imagine that if I dated someone who could never afford to eat out at all, not even tacos and BYOB, it would be a bummer because I like to go out sometimes. So maybe it’s a bit like that.

      1. I agree, and was wondering the same exact thing while reading the letter and Kate’s post. I have had extremely expensive, elegant, Michelin-rated meals, and I’ve had meals at the local brewpub/burrito place/bbq joint, and they were all equally enjoyable to me, in different ways. Maybe re-adjusting the idea of what a celebratory “special” meal is could help ensure that less well-off friends aren’t excluded?

      2. I keep coming back to this comment, because it keeps bugging me a little, but I keep trying to unpack my emotional response and I might be getting somewhere. I’m not sure I have it really unpacked yet (and there’s some fear of getting yelled at for Not Getting It), so please bear with me a bit, because I’d like to try typing at it.

        For background, my childhood included some times when there wasn’t a lot of money (but not going hungry or in danger of having things turned off). I’ve been a broke college student, half of a spending-more-than-we-make marriage, a professional making ~$35k and no debt (but renting), and now an unemployed housewife.

        When I read this comment, it seems like the underlying idea is that the person is thinking “An awesome thing happened! I want to celebrate with friends! Where should we go? I know! Expensive Place!”. For times like that, with one caveat, I agree that when the focus is “celebrate with friends”, making the shift to Less Expensive Place My Friends Can Afford is a cool and fairly easy thing to do.

        My one caveat is that I am rarely willing to go to the chain places, even if they are less expensive. I can’t stand the oversweetened, over-productionized food, and I don’t think it’s good for me. I love my friends, but not so much that I want to celebrate my special thing by eating food I don’t like at all. However, I adore finding the little mom-and-pop and/or ethnic places that are just as, if not more so, not-expensive. Or they could come over and I’d make food. Many times the equation IS “friends + tasty real food = celebration”.

        Sometimes, though … the thinking goes like this: “I did this awesome thing! (Raise! Completed my degree! Paid off my loans!) I want to reward myself with something Really Nice, like going to the Expensive Place. It would be really cool if other people could come with me to share that.” For that kind of thing, going to someplace special, that may be more expensive than what I would be willing or able to spend on any kind of regular basis, IS part of the celebratory experience.

        This can be very much a relative thing. Sometimes for me this has meant “sushi place”, and rarely the “$60 per person really fancy place”, and sometimes “Village Inn”. YMMV.

        I don’t see myself as hugely materialistic or All About Teh Moniez – I’m much more about having Awesome Experiences. Experiences can be sometimes/often cheap and sometimes free!, but sometimes the one you want isn’t. They aren’t always interchangeable.

        Hopefully this isn’t too Explainy or Lack Of Clue-y or Putting Words In Your Mouth-y. Money is complicated and I’m still in the throes of trying to figure out some stuff around it myself.

  3. I agree with Kate. I’ve been in similar situations to LW’s. I grew up wealthy, but also from a very left-wing progressive family, and I never got along with most of the kids from the posh private schools that I went to. I’ve lost a few important friendships over the years from being in situations where a friend fell on hard times and requested financial help from me, accepted it, and then never got over feeling ashamed and resentful about the situation. I can understand those feelings (I feel similarly resentful of relying on my parents financially at times) but I get really sad about ending up in that kind of bind. If I say no, then my friend is in trouble, and is mad at me for being able to help and not doing so. If I say yes, it poisons the friendship in a different way. I never put any strings on that kind of help, for the record, and all of the yucky and complicated feelings involved are understandable, I just wish I knew how to preserve friendships once the topic has come up.

    I also once had a long-term dating partner admit to me that one of the biggest reasons he had agreed to try to work on taking the relationship to the next level (deepening it, thinking about moving in together, eventual kids, etc.) was because he was broke and in a lot of debt and combining finances with me would fix those things. At the time he thought that was OK because we would “both be getting something that we wanted.” I wanted a life partner, and he wanted financial security. Hearing that from someone I had known and loved for years has made me pretty anxious about revealing my financial situation to people I’m dating. I draw the line at deception, but I try to delay talking about finances for as long as possible when I’m getting to know someone. So no, no fake apartments in my past, but I can sympathize a bit with the impulse.

    This is a category of problems that I don’t normally talk about with anybody. I feel petty and ridiculous complaining about this stuff when so many people can’t afford the food, housing, clothes, and healthcare. But it can be isolating, and I wanted the LW to know they aren’t alone in struggling to navigate this stuff.

    1. I’m so sorry, both about the lost friendship and about the lost partner. I hope this thread can be a safe place for people to talk about their anxieties and where no one has to apologize for their own luck & success.

      Maybe we can arrive at some kind of unified theory of when is it a good idea to talk about finances (and other important, personal topics where there is some baggage) with someone who is a good dating prospect. Not exactly the same, but related in terms of seriousness: My partner and I had a full “Here is our mental health stuff” disclosure when it was clear that this was maybe the beginning of something special but it was still early enough to bail and give the other person the opportunity to bail if necessary. Nobody’s heart (or parts) had been offered up yet, and the way that conversation went deepened our trust and desire to open up. I can see STDs, or finances, or any other important (possible dealbreaker) issue having similar weight and potential trust issues that need to be figured out pretty early.

  4. I think that the Captain is spot on with exactly what is so horrible about your second apartment you use for dating. While we live in a culture that likes to focus on this whole, “You loved me for who I was, and as a reward, you can marry me and be rich, too!” narrative. This narrative is pretty deeply ingrained culturally as something romantic (e.g. Beauty and the Beast, Joe Millionaire), but doesn’t necessarily make sense in reality. I know that if my partner were to tell me, “By the way, this entire time, I’ve only been pretending to be struggling financially because I wanted to see what kind of person you were,” I would be deeply hurt and beyond furious.

    By hiding your wealth, you’re setting up a situation where the reveal pretty much implies, “You passed the test you didn’t know you were taking.” It’s a massive betrayal of trust.

    I don’t think that you’re a bad person; you certainly don’t sound like one. But I think that it’s important for you to realize just why hiding your wealth and your lifestyle was such a huge mistake. You say that you found your date’s anger completely understandable, but I get the feeling that if you really understood why your actions were wrong, you wouldn’t be writing to Captain Awkward (or at least, you wouldn’t have made the story such a focal point in your letter).

    What should do you when it comes to dating? BE YOURSELF. If you’re worried about women seeing you as just a credit card, then don’t open the conversation with, “I’m super wealthy!” and don’t pick the fanciest restaurant you can think of for first dates. And trust your gut if you think a date is only interested because of your wealth, although I definitely think that “gold diggers” are much, much more rare than pop culture would lead you to believe.

    1. Well, the flip side of this for the LW is also, you spent all this time getting to know this woman to be sure she wasn’t a gold digger, and now… you reveal that you’re not the person she thought *you* were? And now she has to move several spaces back on the game board to learn who you really are? Not just “a person who has money, yay!,” but “a person who is really deeply insecure about things relating to that money, and whose behavior is really affected and informed by those issues.” In other words, it’s not just the money that you’re hiding. There’s a whole side of your personality, of things you’re trying to cope with and work through, that… she’s only just now finding out about. You’re trying to find out who she is, psychologically, while denying that information about yourself to her.

      1. Well said. He’s worried about money-as-power, as in, “My money has power to make you like me even if you don’t really like me,” but he’s using money as control & power = “I will use my money to rent another apartment and pretend to be someone else so I can control what you know about me.”

  5. I don’t care if I get slammed, but I’m going to chime in from a “gold digger” perspective. I am not rich but I’m young and at my time in life prefer to date men with money. However I will make this much clear: I do not lie about my intentions and most classical gold diggers won’t. Our focus by and large is money and experiences afforded to us by rich guys and we make this a focus early on because we don’t want to waste time (for the guy and for ourselves) and we don’t want to break hearts. The men who are attracted to goldiggers know exactly what we are and are happy to spend, and those who don’t want us avoid us – that’s the way it should be. It’s no fun tricking people to get what you want. Lies are not cool no matter how you shape it and I am always about being honest despite what people think about my lifestyle.

    Calculated golddiggers who want to marry/date money by faking emotions are rarer (and nastier) because it is a facade that a person would have to put up for a long time and it causes so much destruction. However, by having a fake apartment, that makes you no different because you are also portaying a lie and your date is not getting to know the real you. There’s something fundamentally wrong with that and I totally get why she dumped you when you showed her she passed your ‘secret test’. Think about it: would you like someone to do that to you?

    I agree with Captain on this. Don’t hide your wealth but don’t make it a focal point. Removing it as a focus will keep the calculated goldiggers to a bare minimum, but will win the respect of women who want to date you for you as long as you let your other talents shine through. If you find mutual attraction in someone, trust it and go with it unless alarm bells go off. Dating with wealth will take some navigating but it will be worse for you to lie to get through it..

    1. Primadonna, I am fascinated by your comment!

      Could you tell us more specifically how the early negotiation stages work in your relationships with wealthy men? Like, are you meeting on some kind of specialized dating site where it’s “understood” that a financial arrangement will be in place or does it just come up in the course of conversation? What are some hints or signs that the LW could look for early on in a relationship that a “classical gold digger” would give off?

      1. Hi Captain,

        Thanks for responding to my comment first of all because I love reading your site and second of all because of the open mindedness you’ve show to my response.

        There are websites to meet rich men and those are very as clear as to what the intentions are – LW would do well to avoid those sites (they make no secret of what they are).

        In real life, it’s also pretty obvious too. I’ll give you an idea:

        – The initial conversation(s) points to picking up indicators of wealth: what job they do, what car they drive/if they are chauffeur driven, where they holiday, kind of house/neighbourhood they stay, where they shop/if they like to shop, etc. Maybe more emphasis on this than on other things.

        – If dining out, the lady chooses expensive restaurants, not flinching at ordering expensive items, and not picking up/offering to share the check.

        – Making requests for money directly and indirectly such as wanting to go shopping or pointing out things they’d like bought for them.

        Men who want a woman they can spend on will be fine with this, as long as he is attracted and likes us. So as well as the above, I make sure I look good and yes, I can be quite flirty too!

        LW would do well to look out for those things and avoid them or maybe confront the women over some of the behaviours if that’s not what he wants.


        1. Good on you for finding an arrangement that makes you and your partners happy. But I have to ask: what’s in it for the guy? I’m sure you’re great company, but other girls who aren’t gold diggers might also be good company, and it sounds like some of the guys actively enjoy being used for their wallets.

          Any idea what that’s all about?

          1. Hi Simone Lovelace,

            What in it for the guy is that:

            – Some are looking for someone they can feel like a man around and treat like a lady , and money is a way for some of them to flaunt their ego and masculinity. A nongoldigger who insists on doing everything herself might demasculinate a guy like that and put him off.

            – Also, I am not looking for love and neither are many of these men. A lot of them work crazy hours and only want someone to destress with when they have free time. So in a way we are placated by the money and have a no-ties understanding. A non-goldigger who might be looking for love may nag the guy to spend time with her if she is not placated by the money. It might be the kind of situation the guy is not looking for.

            – some are looking for a hot girl to be seen with. I make sure to look good and actually quite like being shown off. So there is an element of superficiality that strikes both ways. Not every girl would play along with that.

            There are non-goldiggers who make excellent catches that are in high demand by wealthy men like the LW. But for others, they may not be what the man is looking for at that point in his life. So what’s in it for the guy really depends on what stage he’s at in his life and what he is looking for.

          2. Some guys DO actually enjoy being used for their money. I stumbled on this once when I was considering an arrangement like Primadonna’s.


            Now don’t get me wrong, the stuff described at that link is extreme and isn’t at all what all guys in Primadonna’s partner’s position want. Sometimes the motivation for sugar-daddy-ing is access to the kind of girls (younger, super attractive) that would otherwise be unavailable to them. Sometimes they just want the relationship to be somewhat… transactional. Basically, they don’t want to have the responsibilities/long term ties of a true partner, but they also don’t want a whore. They want someone pretty on their arm in public, and it is honestly no big deal to them to pay for it.

            Personally, I decided I couldn’t do any of it. Financial domination in particular is often done in ways that I find incredibly unethical, but even more sugar-daddy type setups kind of skeeve me out. I don’t find the doublespeak involved to be a fun sexy game, to me it’s just stressful and icky-feeling. I’d rather be a more traditional escort/other explicit sex work if I had to make money off of being a pretty young thing. But some women and men are comfortable with this sort of thing, and as long as neither is ruthlessly uncaring about the other person’s wellbeing, I think it’s fine.

          3. Word. That is some fascinating stuff.

            I will never understand straight men. XD

    2. Fascinating stuff! Thanks for sharing, I really thought this was an interesting perspective and relevant to the discussion!

  6. Sigh. I agree with both sides of the debate? On the one hand, the bogus apartment is deceitful and insulting. On the other hand, disparities in money can make people on both sides uncomfortable and make them act weird. And yes there are people who will (consciously or unconsciously) be more attracted to the LW (or pretend to be more attracted to him) than they otherwise would because of the attraction of the money. Which means it’s not all insecurity or paranoia that makes him fret the issue.

    I went to an exclusive prep school with some absurdly wealthy kids (if I dropped names you’d know ’em), though my own family had to struggle to pay the tuition. My best advice, taken from what seemed to work best, is never to let your money define you. Be understated about it, not lavish. When you splurge, let it be about comfort and pleasure, not ostentation. Of course you want a nice car, and you can afford one so why shouldn’t you have it? But there are nice cars, and there are nice cars…. splurge on comfort and performance, with a dash of style, and you’ll be ok. Go over the top and get a screamingly expensive car, or buy yourself a shiny, top-of-the-line red sports car every year or two…. and don’t blame the world if the people who are attracted to you are the money-grubbers.

    Same with homes. Splurge on space (within reason, and based on what you will actually *use*), windows, quality, comfort, convenience. But if you cross the line into showplace and outfit your home like you’re thinking of it in terms of a magazine spread (and god forbid, do the nonsense of gutting it every couple of years according to what kind of refrigerator or countertop or furnishing is in fashion)… and yeah, that attracts a different sort of person.

    Go out to nice restaurants, but define nice by excellent food and pleasant atmosphere, not trendiness or exclusiveness.

    Don’t do this all as a lie, to hide your wealth — do it as a way to be rich without letting it define you. And if you’re not wearing it on your sleeve, it’s less likely to be the thing that draws a woman to you.

    Other than that, you’ll have to count on conversation and instinct to tell you what is going on with a particular woman.

    1. P.S., I think it’s a little bit like beauty: there are lots of ways to be beautiful. If you choose to take your pretty and artificial it up and make yourself a distancing kind of beauty, for whom beauty is the number one thing people think about when they see you, you’re going to attract people for whom looks are really important. If you take your pretty and say “it’s just part of who I am, I’m not going to try to hide it, but what I really want people to notice about me is how outdoorsy/witty/well read/interesting…. I am so that’s what I’m going to showcase,” you’ll attract different people.

      1. And, in the same way, if you’re fixated on your looks, and terrified of the way people will react to them, your own relationship with your looks will be offputting.

      2. I really liked this and feel it added a lot to the conversation. 🙂 It’s instructive for lots of different situations people find themselves in (me included).

  7. The fact that the LW doesn’t want to associate with other rich people is definitely a sign that he relies on his wealth to gain power over others, and is not comfortable with relationships that don’t have intrinsic built-in power differentials, such as by the elaborate fake-apartment ruse. However, the fake-apartment ruse is also a defense mechanism. Once revealed, if he then gets rejected, he can tell himself that it wasn’t because he lied and manipulated, but because he turned out to be rich. There is also likely a component of the LW not believing that he “deserves” to be rich, and believing that if he lets others see that he is rich, they will judge him also as not “deserving” it.

    I agree the LW can benefit greatly from therapy: to figure out why he doesn’t view himself positively independent of his wealth, to figure out why he doesn’t think he deserves to be rich, and to learn to trust himself and other people sufficiently to engage in relationships on the basis of truth and positive regard for self and others.

    1. LW didn’t say he’d rather not associate with other rich people. He said he doesn’t fit in with them, which isn’t the same thing.

  8. I want to offer a perspective as someone in a relationship with someone whose family has some significant money and are totally weird about it (it’s probably not the “dynastic wealth crowd” level of money, whatever that is, but there sure seems like a lot of $$ sloshing around from my perspective). I do think that wealth disparity is something that has to be handled with care, but that in my experience the more you treat it like a big deal, the worse you are likely to handle it. A couple pitfalls that I’ve encountered that I suggest people try to avoid:

    Secret stash of money: It’s really not that secret. I guess I wouldn’t know if someone really had fooled me, but I can’t say that I was ever fooled for long by people who I later learned actually were trying to fool me. Then it just becomes awkward, like where did you get this money without an obvious origin? Are you an arms dealer or something?

    “I’m rich/you’re poor”: Actually, everyone has relative amounts of money. I may not have massive inherited wealth, but I have a job and I can treat myself to things and give to charity. I don’t live in abject poverty and I don’t need to be pitied or handed out too. Likewise, there is always someone richer than you, and they probably have annoying pity for your mere 3 cars. We all have indoor plumbing and tiny phone computers, so in the grand scheme of things, we’re not that different.

    Paranoia about being sued for all your precious $$$: I think this is self-evidently ridiculous, but I will also point out that you have to do something illegal to actually lose a lawsuit. This is less about dating per se, but it implies that you feel entitled to be above the law, which is not a good look.

    Money is like a guy you know who can get you things. Should you brag to everyone that you know a guy and can totally get into that sold out event and they can’t? Obviously not. But you also shouldn’t refuse to introduce anyone to him and then go stay in his secret second apartment.

  9. LW, I think on a lot of levels this all boils down to one of my favorite bits of advice from the Captain — “people who like you will act like they like you.” Don’t give more than you’re comfortable giving (gifts, paying for expensive dates, whatever) and don’t offer a notarized copy of your investment portfolio on the second date or anything, but just watch for reciprocity and have some faith in humanity and in your own ability to judge someone’s character. Does whoever you’re dating do nice things for you (whether or not they require her to spend money the way you might)? Is she easy to make plans with (especially ones that don’t involve you shelling out a ton of money)? Does she seem honestly interested in the things you like and are important to you? Do you both seem to enjoy spending time together? If yes to those things, chill and just let the financial things come as they may.

    Most people have had some variation on “does this person like me for the right reasons” any number of times over the course of their romantic life. I’d hazard to say that most heterosexual women have had the “is he just in it to get laid?” conversation with themselves at least once, people who are members of any number of ethnic groups have to wonder whether they’re being fetishized by the people they date, “are we still together just because he/she doesn’t want to be single?” is a reasonably common occurrence, and I’m sure there are a lot of other similar circumstances I’m forgetting. The point is that learning to navigate “does this person really like me?” is something that pretty much everyone deals with at some point or another. Get thee to therapy, work on your insecurity, and try and get zen with the reality that there is always the potential for someone to break your heart and it’s a risk we all just sort of agree to deal with.

    One last note about the fake apartment/general dishonesty — the type of person who would happily accept being deceived on that level is not someone you want in your life and the end result is pretty much exactly the opposite of what you want. By going to that length to create a sort of alternate identity, you’re ensuring that you won’t know if whoever you’re dating really likes you for you, because they can’t KNOW you.

    1. “…try and get zen with the reality that there is always the potential for someone to break your heart and it’s a risk we all just sort of agree to deal with.” This is pure truth, and poetic, too.

    2. I kind of love you for this whole thing. YES. Part of growing up– the worst part, I think– is figuring out that there is no right way to avoid being hurt, there’s just learning to get up and go again, in spite of knowing just how bad it can hurt when it goes wrong.

      1. ❤ Thank you! And you're really right, I think. We grow up thinking that at some point we're going to figure out how to avoid getting hurt or making mistakes, and at some point reality smacks us upside the head and is like "dude, nope, not how it works, you just learn how to not be destroyed when the inevitable bad crap happens." It's hard, it's so hard, but it's also a lesson that the sooner you learn it the better.

  10. I want the letter writer to read Strong Poison and find out what Harriet Vane thought when her ‘opposed to marriage’ partner revealed it had all been a test.

    Mutuality requires honest communication – if you don’t give it, you won’t get it.

    1. Oh hell yes. DL Sayers was my first relationship tutor.
      (DL Sayers shout-outs aside, I actually think it really might be a useful book for the LW to read. Strong Poison and one or two of the sequels; there’s a running theme of the difficulty of equality and reciprocity and independence in relationships, and even about financial inequality specifically. And it’s very interestingly handled, and still surprisingly up to date for having been written in the 1930s).

      1. I love DLS too! I think it’s not that the novels are up-to-date as that the times we live in now are ridiculously, cruelly like the 1930s. I mean, imagine if Harriet were *still* tryng to pay off her student loans from Oxford!

      2. What a good call. DL Sayers really does deal with the wealth disparity issue straight-on; in addition to Strong Poison add in Gaudy Night. (And I think the one right before it?)

        1. “Strong Poison”, “Have His Carcase” and “Gaudy Night” are the first three with Harriet Vane in them. “Busman’s Holiday”, the final one, is only for those who, having read the romantic lead-in, now really want to see the Happy Couple Is Happy thing go on for an entire novel 🙂 Which I did, btw.


      Minor caveat: The manipulative test-giver in Strong Poison starts out dead and stays that way through the remainder of the novels. So maybe don’t pay too much attention to that part.

      Fortunately the fabulously wealthy paramour is still alive and kicking at all the important points in the story.

  11. When I was in my mid-20’s, I learned that I was in line to inherit quite a bit of money–approx. 10 time my annual salary. I discussed it with no one other than my brothers, who were also about to inherit the same amount. Because of complicated problems to do with having a bank as a trustee, my brothers and I signed this money over to other family members. This was all done amicably and we did not resent this solution. When I was in my mid-30’s, I again inherited money (not as much), and this time I got to keep it. Again, I told NO ONE. One day, the money I placed in others’ hands will make its way back to me.

    I live very modestly on the money I make. I have, at times, been actually poor, with only $1 in cash and an overdrawn checking account (early 20’s). I have waited impatiently for the check to arrive in the mail and had to do some fancy economizing when it didn’t. I did know that I have an enormous net underneath me, which gave (and gives) me peace of mind and more opportunities to pursue my passions. And, the ability and desire to be generous.

    So I have been both poor and well off and will one day be even better off, and who know, maybe even poor again. I have tried to be consistent in my lifestyle. I’m not especially ostentatious, but I like to buy presents for my nieces and nephews and the children of friends. I didn’t buy my dream home–I bought a house valued at approx. 2/3rds of what I could afford. And when I lost my job and had to live off my savings, I was very glad that I had done so.

    LW, I understand your problem, and it is a real one. My advice to you is to downsize and downscale. Spend your money on experiences or causes, not things. And if you can afford it (as you can) buy quality rather than quantity. There’s nothing wrong with liking nice things. I buy really expensive shoes. When they wear out, I have them re-heeled.

    I think lying about your financial status is a bad idea, but being guarded is not. We live in a society when conspicuous consumption is valued, but direct questions about cash flow are embarrassing. There are plenty of people who live in fabulous houses with many toys who are right on the edge of bankruptcy. And then there are plenty of people like Warren Buffet who live in modest brick ranchers who have far more money than I could ever imagine.

    If you don’t have a job, why don’t you get one? Try living on that income or put yourself on a comparable budget.

    You are in your late 20’s. As you get older, your friends will become more financially stable (I hope, for their sakes!). But you should still seek out all kinds of people, so that you don’t become insulated from the world where it is a struggle to come up with daily bus fare. You will find that you have the ability to move among all levels of society, if you keep the right attitude.

    I’ll give you an example from my life. I ride the bus to work. I’ve befriended some kids on my bus route. They live in the projects; I live in an adjacent, re-gentrified area. I will take books to read to them–books I buy at the used book store for 25 cents. If they really like a particular book, I give it to them. This is the same way I treat my nieces and nephews. Used books and library books are the best deals in town, and I love a bargain! I’m also active in crime prevention efforts in my area. Next week, an organization I volunteer with will have a meeting with the mayor. My interaction with these kids and my access to the mayor may actually help me improve my neighborhood.

    Money can be a terrible force. That sounds melodramatic, but I have seen disputes over it rip families apart. I’ve seen people come into money and quit their jobs and lose their identities… second-cousins twice-removed and previously unknown step-children file lawsuits…people who have become compulsive shoppers or spiraled into drug addiction with the additional income.

    It’s actually HARD WORK keeping up with money. You do need to surround yourself with professionals you trust when it comes to the nitty-gritty, like tax filing and investments and charitable giving. All those nice material things (my shoes! my books!) can become a terrible burden when you are trying to move or settle an estate.

    I’m looking back over my advice and I’m afraid it’s going to sound like I am saying, “Be more old money about your money.” When I was young, my parents took considerable steps to convince my brothers and me that we were poor. I heard, “No,we can’t afford that [not true]…no, you don’t need that [probably true]…look at the labels and tell me which type of cheese is the better value, the pre-shredded package or the block? [the block]…I’m not buying you new jeans just so you can outgrow them; see what you can find at the thrift store [but, Mom!].” I have a friend whose family struggled financially after the death of her father. Her mother tried to convince the kids they had no money worries at all. All of our parents did the best they could.

    Live like you are immune to your money. Look at it as a useful tool. There are studies out there on lottery winners (sorry, blanking on the author) and the general conclusion was that: people need enough income to meet basic needs and then a little bit for extra. People are happiest when they have sufficient funds for food, shelter, clothing, transportation, health care, AND some to splurge, to share, and to save. The increase in happiness is not proportional to increase in income.

    I would also encourage you to seek some spiritual guidance, if you are so inclined, where you can focus on the eternal rather than the temporal. (And, seriously, NEVER tell a religious or non-profit organization that you are wealthy). I dislike people who quote from the Bible AT me, but I am going to paraphrase some verses that were helpful to me: “Take care that you do not give your alms before men” and “When you pray, do not pray like the hypocrites on the street corner, to be seen by men.” Sorry for the gendered language, but it is the culture of my youth, and I still find meaning in it. The references are Matthew 6:1 and Matthew 6:5 if you want to look up the complete citations. I have always been a generous person–and, this is key–I was even when I didn’t have a steady cash flow. But I have always been simultaneously private. You are in the unique position to do a lot of good and I think once you commit to something close to your heart you will find that you attract people for yourself, rather than your bank account.

    And now it sounds like I am challenging you to become a do-gooder, and that’s not exactly what I want to convey either. Go ahead and have fun!

    1. “I live very modestly on the money I make. I have, at times, been actually poor, with only $1 in cash and an overdrawn checking account (early 20′s). I have waited impatiently for the check to arrive in the mail and had to do some fancy economizing when it didn’t. I did know that I have an enormous net underneath me, which gave (and gives) me peace of mind and more opportunities to pursue my passions. And, the ability and desire to be generous.”

      I’m in a really similar situation, and I think your advice is spot on. It’s a weird spot, isn’t it?

    2. I know that the LR originally was concerned about relationships, but I think your response was the most thoughtful and best so far!

      The fact is, if he wants a true romantic relationship, he should also be thinking about his future. If he spends all his money without paying attention to the bills piling up (ala many movie stars who went bankrupt) he won’t have the funds to help his possible future children through college, etc.

      I always told myself that if I ever got rich, I would do exactly as your parents did for you. I would never spoil kids and would help them to see the value of life and existence for life’s sake, instead of the empty value we find in material possessions.

      Becoming a do-gooder might not be what he wants, but many wealthy have said that they found a new reason to live after they began “doing good.” In fact many commentators have discussed how “paying forward” has given new meaning to many people’s lives. Perhaps he should try to think about how much power he really does have – and how in a way, it is a responsibility. He can either chose to deny responsibility and live lavishly, or he can consider and possibly accept such a weight. Along with it comes a strong sense of self and being one with the world around you, though. LR, if you use the power of your wealth “for good” instead of “for you” (and of course, I hope not “for evil”!) then you could really make amazing changes for humanity.

      Just something to think about, LR.

      1. Dur, learning a foreign language made my English dumb. LW!!! Sorry. *hides sheepishly*

  12. You know, I’m a lady who is economically comfortable now but had precious few resources for a very long time (doctorates will do that to you). And while I don’t know that I’ve ever dated anyone as bananas rich as LW is suggesting he is (although–maybe? It’s possible!), I’ve definitely dated some wealthier men (which we might define as “men for whom it was feasible to drop money on purchases or services that were roughly equal to my rent”).

    And you know, it went more or less the same as when I dated men who were in my income bracket. Usually, we split costs, because that’s how I roll. We made dinner together a lot, because I like that. We went to things I never mind paying for, like plays and museums. The only difference between dating a six-figure-salary dude and a fellow TA is that occasionally, the former dude would want to do something together that I couldn’t manage (a brief vacation, nice dinners during the summer when my TA compensation wasn’t available), and he would offer to treat (as described by some commenters above) and I would accept. Sometimes, I would accept with conditions: you can get dinner but I’ll get tip; thank you for the plane ticket, I’ll split the hotel with you. I went on in this way for three years with a dude, and although we were not compatible for a long term relationship, we had a nice time and he is still a dear friend.

    It turns out, money matters can be managed the same as sex and relationship issues: by using your words, and taking one another’s words at face value.

    1. Yes! There are many many things to do that don’t require large sums, that show that you care, and can be fancied-up or fancied-down as much as you both would like!

  13. I have this friend that works at a liquor store and gets me very cheap alcohol. (This can be a mixed blessing.) The very nice bottles of wine for very cheap prices are fabulous. We drink a lot of them together. But if this friend were less fabulous in himself? I would just pay for my alcohol elsewhere, because if someone does me a bunch of favors who is not my friend, then I feel beholden. And who likes feeling beholden to a person you don’t particularly like? Nobody. LW, for most people, your money is maybe a minor positive, like someone who makes really excellent cupcakes on a frequent basis. Oh, sweet, we get to eat tasty cupcakes (or, in your case, go to a fancy restaurant). But the best part is tasty cupcakes (or wine, for me, or dinners, for you) with a person that makes you happy.

  14. I don’t understand, LW. If you don’t want them to see your real apartment, why offer to take them back to your place at all? Not sure I agree with the Comradde’s assessment that you must enjoy the power differential. If you didn’t grow up wealthy, you probably don’t feel like you fit in with that crowd, anyway. Class hopping is difficult and totally consuming–especially if you’re making a SIGNIFICANT jump upward.

    I was thinking of “wealth” like size, rather than general beauty. I’m particularly fat, so when I was dating, I came across my fair share of chubby chasers. I’m comfortable with a guy who finds my body type attractive, but I was uncomfortable being with a guy who made my appearance a fetish-type-thing. Also, many guys in that scene (NOT ALL. GOOD LORD, NOT ALL) are looking for someone they can prey on. But you know what, LW? Those people were REALLY obvious once I’d met a few of them. That’s what they talk about, that’s what they focus on, and the other fun conversation and activity is decidedly missing. Now that you’ve had a few “gold digger” experiences, sounds like you’re in a better place to use your best judgment about why people are talking to you.

    But that nagging voice in the back that suspects even the best partners are just with you for the money? That’s what therapy’s for.

  15. As a woman who doesn’t give a crap about a guy’s money I can assure you LW women like that exist.

    I’ve dated the spectrum of guys. From guys who are dirt poor and are working two jobs just to pay for an overpriced apartment to guys who had a really good paying job and were living in fancy places. Me being poor, from a poor family, and kind of feeling like money is not really that important made me the kind of girl who doesn’t factor in wealth when dating someone.

    I assure you of this but at the same time I am aware girls can be dicks.

    But I would be really pissed at a guy for lying to me for three months and taking me to his fake apartment. Maybe you shouldn’t have taken her home ever? Maybe you should have broke it to her within the first month you were dating instead of waiting so long?

    If it were me. Which it never would be. But if it were me, I would not bring the person home, not talk about my money or job or income really. I would say I make a “decent living” if asked. If I felt like with in the time talking to that person that they really liked “me” and didn’t care about my job/money/whatever I would be like, “Hey, I have to tell you something kind of serious. I didn’t mean to hide it from you but I don’t feel comfortable telling people about it until I feel like I can trust them.”

    Then I would tell them.

    I had a serious issue (not related) that I waited 6 months to tell the guy I was talking to/am sort of “dating.” It was something super sensitive to me. Something that I felt like i should say in person to him rather than text or call him about. So I waited 6 months until we saw each other in person again to tell him it. He took it really well, because I told him I wasn’t trying to hide it. I just needed to tell him face to face rather than via text.

    Regardless, I would follow all of the Captain’s advice. But if you have feelings for a girl and you feel like you can trust her enough to have her over at an apartment real or fake…

    Why can’t you just tell her the truth about yourself?

  16. I have the impression that LW’s financial status is relatively new. I mean, it feels kind of like when I first got an Xbox– it was all I wanted to do and almost all I wanted to talk about for a few months until the shiny wore off. Then I got other toys and went back to reading the news. Now, I imagine massive wealth takes a lot longer for the shiny to wear off than other new toys or ideas or ways of being, but I think part of the LW’s seeming deal with money is that it’s still pretty new and shiny and other feeling (like, “I can’t believe this happened to me”). So, one thing that the LW should work out in therapy is getting used to the feeling of wealth so that it can become A thing about the LW and not THE thing about the LW.

    I grew up dirt poor and I’ve stayed pretty poor while I was seeking my education. I’m better off now with my husband and I both working, but we’re not exactly rolling in it. My parents are decently off now– they just retired with a paid-off mortgage and a good pension. My in-laws, however, make 2 cents more than god. My MIL is a major banking executive and my FIL has a size-able trust fund. So, I understand a bit about navigating relationships where there is a clear financial disparity.

    Here’s the surprising thing– I never feel poor when I’m with my in-laws, but I usually feel poor and cranky when I’m with my parents. Here’s why. My mother is only capable of talking about 3 things– money, her cats, and her TV shows. She has no other interests and she doesn’t care to talk about other people’s interests. She makes money THE thing about herself, almost the only thing about herself. And when you only have $20 in the bank because you had an emergency it is really difficult to hear someone talk about how they have half a million dollars in the bank. I’m happy for my parents, I really am, but it also hurts my feelings that we can’t find and talk about something else we have in common. It also makes it difficult to accept any gifts or help from them because it feels like they’re so aware of every penny that it’s a huge deal to accept anything. I’d be terrified to find how many strings were hiding at the bottom of the gift.

    My in-laws, on the other hand, will talk about money if it comes up naturally in a conversation, but otherwise we talk about other things– current events, technology, food, cooking, gardening, the list goes on because we all work hard to find some common ground. The money is one thing about a pair of gracious, interesting people. If they would like to treat us to something or help us out in some way, they offer and if it’s something my husband and I would like to accept, we do. If we don’t accept, there’s no guilt or worry about why we didn’t. Generally, we write thank-you notes and share interesting books.

    I think, to a certain extent, that a money dynamic also came into play when my husband and I were dating. We were both in grad school and he was living at home. I was living in a crappy apartment and working two jobs to make ends meet. My husband usually had a lot more money than I did. He never lorded it over me, and we were pretty equal in effort. We also did a lot of things together that didn’t take much (or any) money because those were the things that we were interested in doing. We played games together or we’d have a contest to see who could find the weirdest movie in the dollar bin then go order a pizza and watch it. If your interests sway mostly towards things that take money to enjoy, you’ll probably be happier with a more monied partner who will have more access to the things you enjoy and more ability to reciprocate. If your interests are less expensive to pursue, then I think you’ll find that your partner’s income matters less because you’ll naturally be doing things that you both enjoy so the financial imbalance will come up less often.

    There were times that my husband treated me to something nice and a few times that he bailed me out of a financial jam. I guess I have a few observations there– 1. people will take their cue from you, if you treat it like a big deal, then it is a big deal. 2. If the invitation feels natural to extend, then it’s probably fine for the relationship you have, but if it feels awkward, then it’s probably not. 3. Don’t get too extravagant with your gestures (financial or romantic) too soon. 4. In case of financial emergency if you want to help, it can actually bring you much closer together to negotiate what type of help you can give vs. what she can accept. People won’t always feel able to accept everything you feel able to give. Being able to talk about the hows and whys of this without judgment will tell you much about each other. 5. Never feel obligated to help if you don’t want to. It may change or end your relationship, but I think the lack of generous feeling is telling you something important about your relationship that is worth paying attention to.

  17. I have been friends with some wealthy people. But they were non-materialistic and didn’t have flashy cars or clothes. I only figured out they were wealthy due to how generous they are. Also, their parents’ houses gave them away. They are secure and treat money like no big deal.

    The issue I see in the letter is that the LW likes flashy stuff- people react to that. Flashy stuff attracts similarly flashy people, or people who want to benefit from the money.

    So, the LW may be better off reducing the materialism. You can be wealthy and still live and act modestly. You can have a nice car and clothes that don’t drip with wealth. The issue here is one of values. Modest, non-materialistic people, rich or poor, will not be attracted to someone who is giving the message that they are materialistic (I.e., through the nice house, clothes, car).

    The LW would also do better to communicate that having the money is no big deal. That would attract people who similarly think the same thing, whether they are rich or poor. By having a FAKE apartment, it communicates that the LW thinks money is a huge deal. The lying is such a major turn-off, but worse, it sends the message that the money is really important and tied up with all sorts of Money-Feelings and insecurities.

  18. Hey!
    I`m not sure how good advice it is, but I think the LW is underestimating all the nice women who might like him for himself (money included?).
    My only experience is through my sister, who dated a really rich boy when she was in highschool. They dated for 3 years, I think, so both our families got real close, and my sister really liked him. Also, she likes to be spoiled – not necessarily with money, but with affection and attention; but she does likes to go out to eat, and to travel and, since she doesn’t have a license, she likes someone who can take her out. Did she date this guy for those specific reasons? No, she loved him to death for who he was. The thing is, even though she liked going out and being spoiled, she was just happy with his company. Him being able to take her out was a nice perk, but it’s no basis for a long-lasting relationship. They talked for hours, and he would come spend vacations at our (poor, decaying) house, and they would stay home, and cook, and watch movies. He gave her really expensive gifts, which she had no way of ever repaying (financially), so she cooked our families’ specialties for him and his family. She made things for him and taught him things. His family would take all of us to their beach house, and cook expensive stuff (they were really genuinely nice people). We would receive them on our poor house and cook delicious stuff! (in the end, he broke up with her and even his family got sad)
    Really, money differences CAN be a problem in some relations, but I think maybe you should look for people for whom it WON’T be, because it doesn’t have to. If you want to take a girl to an expensive place because it’s nice and you think she will like it, do so. Use your words about it, make sure you’re both on the same page about money. But also look for signs that she likes you for yourself. It takes practice, but it’s not so difficult. Do things that require little or no money, go to her place and cook for her, spend time together that is not about money, talk about shared interests, hobbies, joke around, and you’ll most likely find someone you like and who also likes you. That’s how it works, isn’t it?

  19. Oh LW, I can sympathize. It is MEGA HARD to differentiate between the friends who are only into you for your money and the ones who aren’t. Maybe this isn’t as big a thing with people who don’t have money, but for the wealthy money can be HUGE. As a dynastic wealth person, it’s something I’ve also had problems with; I was raised without money due to an agreement between my parents but was later informed of all the zeros when I hit HS and was packed off to charm school. What most people don’t really understand is that money isn’t just cash, it can also be culture. Money informs your experiences in life, and thus plays a hand in shaping who you are and what your worldview is. Having spanned both worlds I really understand your consternation. I don’t like people who grew up rich either, because they have this way of trivializing everything which I find distasteful. I prefer to hang out with people who grew up poor enough to have ambition, but the line between personal ambition and ambition of marrying up can be really darn thin.

    Unlike many others here, I also totally understand the fake apartment. It’s a way to check and see if they like you first, right? You probably feel more comfortable showing yourself in the fake apartment because you’re not wondering about if she’s eyeing you or that antique Ming dynasty vase above your shoulder. It removes the mystery over basic comments like “Oh what a lovely dining room. Is that real silver?” Yes, you’re lying to her, but only because you’re afraid that until you know her well enough to get a read on her she’s lying to you. At least to me, that’s a perfectly reasonable reaction because people lie all the freaking time. You want her to be happy with the pizza-and-movie dates because it shows she’s happy with you, whereas a caviar-and-champagne date may just have her so pleased because hey, how often does a girl land a guy who dines on caviar? I’m willing to bet cash monies that the grand reveal also has a prince charming element to it. Like, VOILA! You liked me as a broke person but NOW WE ARE RICH! We could have been happy poor but now there’s EVEN MORE HAPPY TO BE HAD! It’s just how it’s supposed to work in the romance movies, where all lies are forgiven because it’s not about lying to her, it’s about her being SO SPECIAL that you DONT have to lie to her anymore. Great, right? You’re not saying she’s a gold-digger, you’re saying she’s NOT a gold-digger and so now you can reveal your piles of cash. A fairy tale come true.

    Unfortunately, not everyone sees it that way. From her POV she’s only known you as That Really Nice Broke Guy. You’ve known you were rich from the start, so the grand reveal is a positive thing. From her perspective, you’ve been lying to her all along. If you’ve been lying about the size of your money pile what’s to say you’ve not been lying about the integrity of your character or the extent of your love? You have the advantage of knowing the falsehood was only confined to money. To her, you’ve RIPPED AWAY EVERYTHING.because she doesn’t have the advantage of having the whole story. She ONLY KNOWS that story you’ve told her, so your Prince Charming Twist comes off as really twisted. It’s not about money it’s about trust, and I think you can understand how from her perspective (without the benefit of your knowledge) you can seem like a bit of a lying liar.

    So I guess while I disagree with the Captain’s indignant response, I do agree with her very last piece of advice. Apologize for lying. Don’t try to explain it as a money thing because to her it’s a trust thing. Say you’re sorry. Maybe she’ll accept it, maybe she won’t. I’d dispense with the fake apartment, or at least come up with a better Grand Reveal/drop hints of wealth as you get to know each other better so it’s not a Huge Surprise. I tend to feel forced on the whole money issue and just bring it up immediately/only date guys who dont seem phased by caviar, or who demonstrate interest in me in other ways. (asking about day, etc) Dress nicely and dont hesitate to drop big sums on a good time. Either your date will seem awkward about it or she wont. If she does, then it’s a tip that money might be a problem later on. If she doesnt then great! Previous commenters are right that it’s a hard act to keep up, so it’s actually pretty easy to weed out the fortune hunters early on. Best of luck!

    1. You want her to be happy with the pizza-and-movie dates because it shows she’s happy with you, whereas a caviar-and-champagne date may just have her so pleased because hey, how often does a girl land a guy who dines on caviar?

      Well, but…look, this seems like a simplistic way to describe taste and behavior, a dichotomy between have and have not when it’s really more like have lots and have some. I’d be surprised if this guy ends up with actual Cinderella.

      People without lots of money are not people without options for dining and entertainment and simple pleasure, and people aren’t necessarily delighted by expense any more than they are fixated on it. And not having money doesn’t mean settling for an inferior or modest option. The alternative to caviar isn’t No Caviar for You.

      He might do better to start thinking about money as something that can be useful but is not always even useful to an evening or an event. Or even a meal. Then it won’t be like, Gee, do I offer her the caviar? but, hey, aren’t we having fun like most people do.

      And as other commenters have said, it’s weird to have your date spend a crapload of money on you because…well, people who do that have different scripts in mind. I’ve met wealthier men who thought it was rude and golddiggery that I didn’t get awkward. (That made me doubly awkward later on.) And I’ve met men who think a certain sense of ahem obligation is also only courteous. There is, as readers of this site should know, such a thing as awkwardness in good faith.

      1. Right, also, money (and potential weirdness about) is one of the things ANY of us has to negotiate in early dating.

        1. Really? If both are from roughly the same income bracket, is there more to it than who gets the check this time?

          1. Well yeah of course. Money tears people apart. I mean even the cheque question isn’t exactly unloaded by gender, age, self image, obligation… and more broadly, ideas about where to live, how much to spend on frivolities, whether to spend or save, how much to share finances, what counts as responsible money handling etc etc etc come up in relationships all the time. Just because you’re in the same general income bracket doesn’t mean you’ve got the same life experiences, cultural background and opinions about money and relationships.

          2. – Do you like to save your money or blow it in a once-a-month paycheck extravaganza? If you are a saver who would like to cook dinner together thriftily and you’re dating someone who wants to go out for a big steak dinner and then you know you’re going to have pack a picnic if you want to eat non-ramen at their house for th erest of the month.

            Ditto someone who buys a new computer every year instead of going to the dentist. If appearance/respectable self-presentation is a big deal to you, someone who owns two pairs of pants even though they could buy more pants is going to stress you out, and the relative investment between two pairs of pants and five pairs of pants is well within the same bracket.

            – Then it gets scaled up as commitment deepens: do you have retirement savings, or a new car? Do you live in a place where you’re close to your support networks, or move for a better job? Does one person sink their disposable income into a hobby the other person does not share? I know of a marriage that broke apart for many reasons but the tipping point? _buying too many quilting supplies_, seriously.

            – Within the middle class, there’s definitely also Old Middle Class and New Middle Class. Whether you invest what funds you have ostentatiously or whether you think it’s most tasteful to have a few nice things is still an issue until you get down to the point of actual survival income. For instance, I come from a family of struggling academics – basically NPR people – and a lot of the things we think are in good taste telegraph as kind of miserly and dowdy to people whose furniture matches. The time/money tradeoff will always be a thing, too.

            Surely other people have other examples. I once got into a huge relationship drama over at what point, financially, it’s reasonable to get a dog – one person loved dogs and just figured they’d work it out as it went along because you make it work when you love something, and the other ended up on the hook for vet bills and there was much fighting.

          3. Aaaaaahahahahahahahaha oh my dear God. YEAH there is more to it than that. Ever been a really financially responsible person who falls in love with someone who spends everything they have and then some, and has huge student loans and huge credit card bills? People who make basically the same amount of money can have vastly different ways of managing it, and that can be incredibly explosive in a very bad way.

          4. Obviously the potential money-complications increase the more entangled you become with someone, but the ways in which money can cause weirdness in a new relationship are basically the exact same regardless of how much of it you have. Whether a “splurge” for you is a $200 dinner or a $30 dinner or dinner out anywhere, you’re going to see disparities in how much people are comfortable spending on date activities, or on treating/being treated to, or spending on gifts. Even within the same income bracket, people have wildly variable spending habits and may have pre-existing financial commitments (mortgages, dependants, student debt, etc.) that restrict their ability/desire to spend on other things. People can also have really different attitudes about their money even if they have the same amount of it — a guy who made the same salary I did but who liked to talk about money all the time or stiff servers on tips would turn me off as much as a guy who made a lot more/less than me who did the same things.

          5. Hey, f, it DOES come up in early dating.

            For example:

            Where are we going on our date?
            Who decides?
            Who pays?
            When the check comes who offers to pay?
            Does that feel weird in any way or was it easy and natural?
            Did one of the people “forget” their wallet?
            Was it the person who decided on where they went on the date and ordered expensive stuff?
            Is there reciprocity, like, you get dinner and I get the movie? Or you drove all this way to get here, let me buy you dinner?
            Is there weird gender shit where the man insists on paying and then stares at my tits all night?
            Does the person bring 57 expired coupons for the thing you’re doing (which, be thrifty and take advantage of coupons, but it’s a sign something’s going on).
            Did the person bring a weird extravagant gift to a first date? (Not recommended).

            You’d be surprised how much you can tell.

          6. There have been relationships where I wish that I had discussed it earlier.

            I happen to be of the type that codes money as security and insurance, not splurge fodder. I do like nice things, and I will buy quality stuff that lasts, rather than cheap junk, but, I need a certain cushion to feel relaxed.

            So, the relationship where I discovered that he was 18 thousand dollars in credit card debt and was expecting to pay that with an inheritance? It was half the reason that I broke the engagement.

            Then years later I married a guy who thought that 10,000 dollars was enough to have saved….and when he reached that point he started looking for stuff to spend it on. 10 thousand seems like a lot, sometimes, to some people. However, I was thinking house repairs or a Year’s emergency funds if he was laid off. That amount of money starts looking small when you are dealing with either of those things.

            Money discussions can be stressful even if you are from a similar income bracket. How people think about money can be vastly different.

    2. I can for sure tell you that for a lot of us who do not have money, money absolutely can be a huge thing, especially in new friendships/relationships. It’s hard to be invited to something by really cool people you would love to get to know better and have to say “Sorry, I can’t pay the cover/ticket price.” Not to mention the social narratives floating around in our culture about how poor people are lazy/stupid, and also sometimes wealthier people have this expectation that poor people should be totally comfortable going to an expensive restaurant (in my nicest pants that still have holes in them, and my shirt with only a tiny stain, and my shoes with Sharpie coloring in the sections that have started to flake off)…Some people are fine with it. I am not.

  20. Tthe cruel irony of this letter is that any woman with the characteristics you want- a focus on character rather than assets- is going to react exactly like this ex. My mind boggles at the sheer logistics that would go into making a second apartment look lived in: furniture, food, a whole entire second wardrobe. That’s easier with money, because money is a way to make things happen, but it’s still a ridiculous amount of effort. Fake lives and double think are too hard; I really hope you find a way to love yourself as-is, because it sounds from your first paragraph like you thought the money would do that for you, but it didn’t.

    Captain, this letter pushed a lot of the same buttons for me that it did for you, and I was very impressed with how compassionate you were.

  21. I grew up working poor and have just barely become middle class in middle age, so I don’t have firsthand knowledge of the complications that immense wealth brings. I have known some very wealthy people. but it wasn’t something that was obvious from the beginning. When my friend who was single and employed as a dance instructor in her 20s bought a 5-bedroom Victorian mansion in a gentrifying area, proceeded to extensively remodel the interior into a luxurious showcase, hired an architect and lawyer to negotiate with the city and neighborhood for a variance and construct a dance studio, and employed a gardener to landscape the yard with so many rare and interesting plants, then I could see that we had significantly different backgrounds that weren’t apparent when we lived in a dorm together back in college. Any one of those projects probably cost more than my current accumulated lifetime income. She had a certain quality of life that she was accustomed to, but she also greatly enjoyed bargain hunting at thrift stores, and did not flaunt her wealth and was quite uncomfortable discussing it. She confided much, much later that it could often lead to trouble.

    I think one of the hazards in this situation is the rich person’s version of the Nice Guy (TM) syndrome: someone who feels entitled to attention and a handout because the rich person has money and can afford it, and then can turn ugly real quick when turned down. Even without that, conspicuous consumption will inevitably attract people who are hoping some of the largesse will rain down on them and they can live on easy street by proxy. And even without that ugliness, a wealth disparity can lead to unbalanced relationships, with the assumption that the rich person will always pick up the tab, will always help out in a financial emergency or whatever. And that can lead to feelings of resentment by both the rich person (lack of reciprocity!) and the beneficiary (lack of equality!). And the opposite can also be true–the rich person is willing to always pick up the tab, but then feels entitled to the other person’s time and attention. I suspect that’s an easy trap to fall into, receiving service on demand and people falling over themselves to offer excellent service wherever one goes, becoming accustomed to that VIP treatment, and having that bleed over into personal relationships. The privilege of having one’s opinion always consulted and then expecting the right to offer one’s opinion in every circumstance.

    My very wealthy friend gave me three generous gifts in the recent past. She did not ask me if I wanted them and expected to argue me into accepting the first one at least. She was I think a little surprised at my lack of resistance, but as others have pointed out, we must learn to accept gifts and compliments graciously (assuming they aren’t part of any sort of abuse or manipulation). The former is much easier for me. I decided a long time ago that I was not going to argue about money with people, because I didn’t want money to be so important to me as to create conflict. Mostly, this has to do with picking up the tab at restaurants or whatever. And sometimes it leads to fun games of one of us distracts everyone else while the other takes the bill to the register (teamwork is good!), but then we agree that the other couple can treat us next time. And of course, money is something that needs to be negotiated with the partner. I also realized that if something is (more) important to someone else, I should respect that. So I freely give away books or other small items when the other person is more invested in the subject, and I likewise accept gifts freely when it is clear that the other person has put thought and care into it and is going to insist on it.

    None of these gifts came with strings attached by her, but they did engender some sense of obligation on my part. The first was a musical instrument. I had played in orchestra growing up, but didn’t in college because I never owned my own instrument. I missed it a great deal, but such things are a luxury, really. My friend was both musician and dancer, so it was an interest that we shared. But where music is a sometime hobby of mine, it was a passion of hers and central to her life. Visiting her was always a treat because I was immediately immersed in the local music scene and a musician’s lifestyle. And I think she wanted to share that with me beyond my rare visits and remove at least one of the constraints that kept me from experiencing that in my own life. So she made no demands with this gift, but receiving it, particularly without resistance, creates in me the need to honor the gift by actually using it, not just letting it gather dust. But another constraint is simply time. I already have so many things that aren’t happening because I just don’t have time and energy and other commitments that were already keeping me busy. So trying to figure out when I can take music lessons and what kind of participation I can have in some sort of musical venue when I am unsure of my ability to practice regularly is something I am still struggling with.

    I understand some of the discomfort of being with people who grew up in a culture of extreme wealth. The second gift from my friend was to join her in Australia for vacation. I was unemployed, and she paid all of my expenses. What money I had, I spent on small gifts for everyone back home. It was an amazing experience in so many ways. But I spent a lot of time trying to wrap my head around it and the profound cultural differences and privilege that the other visitors at the exclusive hotel and island resort had. They just took it for granted that people took international vacations every year and so on. And I really couldn’t get my friend to understand the gulf. I mean, she knew enough to understand that there was no way I could ever travel to Australia on my own. But she didn’t really grasp that my family never took vacations ever, and that I hadn’t seen much of my own state, much less such national landmarks as Yellowstone National Park. I had never been to lots of places because I simply couldn’t afford the time or money–travel is a luxury, really, including relocating to another city for work.

    She once recounted her first shocking personal experience with anti-Semitism when she was a teenager in Paris for the first time. I could sympathize with her pain and realize that she experienced racism that I will never have to deal with directly because of my white privilege and that I was clueless about for much of my life. And yet, I was also smiling because her first(!) time in Paris was when she was a teenager on a class trip. I missed all of those class trips growing up. I hope I might be able to visit Europe for the first time next year now that I have recently achieved enough income to become middle class. I also got really angry with her when she dismissed Australian cuisine as being British and therefore boring and Sydney as being uninteresting because all cosmopolitan cities are alike. So she was completely uninterested in exploring either the local food or the city life because she thought she already knew what there was to know about based on her extensive travel elsewhere and her assumptions. So all of that was quite an experience and a challenge for both of us, I think.

    I’m afraid that little of this really helps LW much. Therapy definitely sounds like a good thing, to help come to terms with the profound changes. And a lot of reflection on what that wealth signifies, on life goals and personal values, and the dynamics of current and future personal relationships. As usual, it will require honesty and communication and care.

    1. YES YES YES YES. Especially “can turn ugly real quick when turned down.” Consent is important, even when you think you’re doing something nice and no-strings-attached!

      And “a wealth disparity can lead to unbalanced relationships, with the assumption that the rich person will always pick up the tab, will always help out in a financial emergency or whatever. And that can lead to feelings of resentment by both the rich person (lack of reciprocity!) and the beneficiary (lack of equality!)” – I have two friends who are partnered, and one is employed and the other is the most fabulous homemaker in the world, and they struggle with this (but fortunately communicate well and really love each other).

  22. 1. LW, It seems like the whole “fake apartment” gambit is actually an EXCELLENT way to make sure that women interested in you as a person will become furious and leave, because the only person who finds the whoops-here’s-my-real-rich-person-apartment reveal to be exciting is someone along the lines of the “golddiggers” you are so terrified of. This is one of the creepiest things I have EVER READ.
    2. I’m a little puzzled by the many people saying “LW, I understand where you’re coming from!” Because, here’s the thing– if LW had written in about his many times being burned from women wanting him for his money, and asking for strategies that would help him deal with that, then sure! Financial disparity in friendships and romantic relationships CAN be really tricky.

    But! SECRET APARTMENT! That’s not a rational coping mechanism. That’s “my boyfriend won’t communicate with me so I crafted multiple online identities and false relationships with him in order to understand his innermost thoughts, and for some reason he was upset when he found out his new friends had been me all along.” That’s “my husband didn’t want kids, so I faked a pregnancy to get him used to the idea and when he discovered the pillow under my clothes he was suddenly angry for no reason.” That’s “my wife doesn’t really like my dog, so I told her she left the back gate unlatched and the dog got out and was hit by a car, and then she was mysteriously incensed when I brought him home a week later.”

    LW, you are not the Marquis of Saluzzo, and the women you date are not variable Griseldas who need to be put through a series of manipulative tests in order to gauge their loyalty and fidelity. There are legitimate difficulties about your situation, but skipping all of them to go straight for the horrifying romcom solution of nonsense seems painfully immature.

    1. Yeah, to me the fake apartment gambit sounded like some weird reality TV show where Ordinary Women (TM) get to date a guy in a competition and in the end, the one he picks is in some massive reveal where – ta da! he turns out to have been Daddy Warbucks all along! Not only does she get the guy but also she gets his money! and a lifestyle! with designer clothes!

      See how the cameras close up on her face as she expresses surprise, tears, gratitude, wonder!!

      In reality there are no cameras and it’s creepy to find out the guy you were dating was lying to you.

      I would think, what else are you lying about? I’d think that shortly before running out of your Mega Bucks house.

      1. I had that same exact response to the reality show that used that plot. I forget its title.

        But, seriously, why would I date someone whose been lying to me about anything?

    2. I’ve got to concur with saythisword and the many other commenters on this one — finding out that someone had put that much time and effort into lying to me, much less the money necessary to create the illusion of a whole second life, would send me running in the other direction as fast as I could go. I’d be some combination of utterly furious and completely devastated, and I would never ever ever want to acknowledge his existence again. So yeah, the second apartment thing is completely counterproductive.

      I’d also be more than a little concerned about substantial differences in core values between myself and someone whose reaction to having that much extra time, effort, and money to spare was “I’ll make an elaborate second identity for myself!” rather than spending that time and money on somehow making some part of the world a little bit better. I’m not saying don’t spend money on fancy and/or frivolous stuff, but making an investment that big in something I find morally reprehensible… not likely to indicate compatibility.

      1. Yeah, everyone has said this but it reads to me more like finding a shelf of pickup artist books in someone’s apartment than being distressed because they buy you a nice watch and you got them a used book – it comes across as substantial time and investment in controlling your reactions and emotions instead of trusting you to make your own decisions. I’ve been really interested in the comments on this thread saying that from the other side it starts to make sense.

    3. seconded all those things. I might also be kind of frightened, because the fake apartment scheme would show that you were engaged in a massive deception, and the manipulative component of it would make me concerned about what other manipulations you might try, and how far you might go.

  23. So I think I’ve got something that hasn’t been covered yet. LW, in my experience the difference between rich people and poor people isn’t so much about what, precisely, money can buy—it is easy to resist other people’s temptations; people who can’t afford it don’t sit around dreaming of yachting—but rather of the level of concern that’s involved. It’s the difference between “ugh, I dropped my phone and now it’s cracked and I have to have a cracked phone for years” and “whatever, I’ll get a new one.”

    I remember in freshman year of college my newspaper board went on a retreat to a member’s house—a four story ski lodge made out of a converted barn in Vermont. It was enormous, and fabulous, but really the thing that made the greatest impression on me lay elsewhere. When we were trying to plug in the iPod to the sound system it wouldn’t work (duh. it never works) and after two minutes our host shrugged, and /bought the entire playlist again off of iTunes/. It was like 80 bucks. Compared to everything around us—hell, compared to the booze!—it wasn’t that expensive. But the fact that he could simply say, “eh, this is too hard, I will solve it with money instead,” was such a clear indicator not of wealth in some numerical sense, but of /being rich/.

    I think your apartment reveal has this problem. Rather than concealing your wealth; rather than letting it come up as and when it does, or even keeping it low for a while, you choose a path that involves a very strong display not of money, but of indifference to money. You have a problem—you’re concerned about how your wealth comes across—and you can throw literally a whole second apartment’s worth of cash at this.

    I know there’s a lot of very, very good advice above. I just want you to keep in mind that concealing a fact is no good if the reveal will exacerbate the negative impression you were trying to avoid in the first place.

    1. Seconded. As someone who grew up poor enough that throwing out food (that I am not hungry for, that is past its expiration date) is emotionally difficult, I know my kneejerk reaction to this kind of massive indifferent display of wealth is very negative. Especially indifference to amounts of money that someone poor but frugal could probably live on.

    2. I’ve been trying to think of situations that I know of where money created a lot of conflict between friends and honestly the main examples I’ve got are all ones where the richer person didn’t understand that they were creating a hassle. For instance staying with a person who was really struggling and, idk, drinking all of their orange juice and not getting more orange juice does suddenly move from “well that was kind of a dick move, now it’ll be two weeks before I can buy new juice” to “WHY MUST YOU GRIND MY FACE IN OUR CLASS DIFFERENCES” once you know that someone’s parents are millionaires.

  24. I’m a graduate student, and I’m fortunate enough to be in a field where the norm is a stipend that is enough to live on, but my income is limited and won’t be going up for several years at least. Last year I dated a guy only a few years older than me. He grew up poor, but ius smart and massively talented and now makes a solid 6-figure salary plus mind-blowing bonuses every other year or so.

    I won’t lie–the money disparity WAS difficult for us. But not for any of the reasons you are imagining–I was not at all a gold-digger, and I actually considered NOT dating him when I found out about the money because that power imbalance made me uncomfortable.

    He was glad to pay for things, but I felt constantly guilty about how much he spent on me, and how little I had. I also resented him sometimes for just not GETTING the fact that me and my grad student friends thought about money very differently from him. Early in our relationship (3-4 months in), I got very sick and spent a night in the hospital and then several days pretty much confined to bed, dependent on painkillers and sleeping a good 18-hours a day. He had an iPad and loved playing fun, silly games on it, so on the way home from the hospital, he bought me one so we could play together in bed when I was awake/feeling well enough to do so.

    My friends were in awe of this guy who could buy me an iPad like someone else would buy me ice cream or a get well card. There were occasional jokes about me hitting the jackpot by landing my rich guy. And there are definitely things I’ve done in the last year that I just wouldn’t have done without him in my life, because I couldn’t have afforded them. But I wouldn’t have stuck around to do them if I hadn’t also enjoyed HIM, because the insecurity I struggled with about HIS money was frankly a lot for me to cope with. I didn’t stick around because of the iPad, I stuck around because he was the guy who stayed with me for 48 hours while I did nothing but play games with him and sleep, just because he wanted to take care of me.

    Today, rich guy and I are friends but not romantically involved, for reasons other than money. I still let him buy me dinner when we hang out, if he offers, but every now and then I will pick up the check, or pay the tip, or for parking, just as a way of signaling that I don’t expect him to cover everything. And I still have roughly 4k in credit card debt that I am paying off agonizingly slowly, even though I probably could have gotten this guy to pay it off in a heartbeat had I asked while we were together. Basically, I could be in much better shape financially if I were willing to be a terrible person, or at least a bit manipulative. I wasn’t.

    Find a girl with her own goals and ambitions and pride, who appreciates your gifts but doesn’t demand them. I don’t think this will be anywhere near as difficult as you think.

  25. I’m curious as to how you, LW, thought the conversation would go when you told your girlfriend that you were actually super rich? How did you picture it? Did you think she would be happy, thinking that all along she had done the morally right thing of loving the frog when really she won the prince? Or did you expect sympathy and understanding about your problem of being too rich to be seen for your personality? What kind of reaction would have made you happiest?

    I’m not asking that to be snarky. Ok, maybe that is a little snarky. But really, answering this question for yourself might give you some insight about what you are really looking for and what you are really afraid of. Did maybe a little part of you hope she would get angry? Why did you pick this particular moment to do a grand “reveal?”

    To really answer your question, beyond seconding the Captain’s suggestion of therapy, I suggest letting your relationships take a more natural course. You aren’t obligated to tell someone your net worth on a first date. If your manner and material belongings scream “I’m unbelievably rich!!” and you aren’t comfortable with prospective girlfriends knowing that about you, maybe ask yourself if you are comfortable with these things yourself? Having a car that makes you feel embarrassed and on display may not really make you happy. Just because you can afford to be ostentatious doesn’t mean you have to be. Do things with your dates that make you feel comfortable and that make you happy. Have a nice apartment, but don’t tell your date what it costs the first time she comes over. Let the “reveal” come naturally and don’t make a big deal out of it. But first, ask yourself what really makes you happy vs. what you have been spending on just because you can. It might bring your own values into focus, which will make them more obvious to prospective girlfriends and attract a compatible match.

  26. I really wonder about where the LW lives and how he made his money. This is because, in my opinion, he dramatically overestimates how out of place or special he is (in the nicest possible way). He rules out hanging out with dynastically wealthy, but there are tons of people who are wealthy who are not part of the Kennedy family, they are called the Educated Wealthy, so I wonder why he feels so lonely? I really doubt that he is surrounded by golddiggers. I mean, didn’t he go to college? Did he not meet educated people with nice summer homes in Cape Cod or Cape Cod equivalent? Did they really seem that different? I also wonder how rich the LW can really be? I mean he says that he earned his money and unless he is Mark Zuckerberg’s alter ego, he can only be at best, investment banker rich. That’s really not *that* much money.

    I am guessing that the LW can’t live somewhere like New York or London. If so, move there! No one in NY will care about your money because there will tons of people richer than you and better looking than you, and even poor people make six figures. I’m NY poor (I make mid six figures). I live in a tiny alcove studio in the UWS and could never afford to buy property in Manhattan, never mind the UWS. I’ve hung out with investment bankers and venture capitalists who make millions every year. I don’t see any *real* difference in the way they behave compared to douchey lawyers (I’m a lawyer for my sins) who make six figures. Slightly nicer bars and much better scotch, but culturally identical.

    1. I’m wondering a bit about where the LW lives too… I mean any large population center has enough self-made millionaires that the letter-writer should be able to meet people in the same league as him, or at least people who won’t be SHOCKED at what league he is in.

      LW, you don’t have to say where you live obviously, I’m just a little surprised that there is a place in the states where you wouldn’t find other people like yourself, that’s all.

  27. LW, do not lie. Women of character are not interested in dating lying liars, however much money they have.

    If you are worried about gold-diggers, I’d recommend that you be vague but truthful about your financial situation. As in, “I’m well-off enough to do X thing, and I’d love to treat you.” As in, “I don’t work because I inherited money.” It isn’t necessary to quantify (yacht money, private island money, whatev) and women who are Very Interested in exactly how much you have are telling you something.

    Also, take your time. If you think showing someone your apartment is telling too much, too soon, then don’t. (Or put that Rembrandt somewhere less obvious.) Go out on a bunch of dates. Get a sense of how you and your love interest treat each other. If she says, “I’m uncomfortable going to X restaurant because I could never afford it and I have nothing to wear,” don’t go Pretty Woman on her and offer to buy her a dress. Go to a different restaurant. There is delicious food at many price points. If she offers to treat you, let her. As you grow to trust her more, you can reveal more. I’d recommend that one thing you reveal is that the money thing kind of freaks you out. (If your hypothetical lady friend is anything like me, it will freak her out, too.)

    Good luck. Your thing with the apartment was a jackass move, but that doesn’t make you a jackass. Learn from that mistake.

  28. For LW:

    You might try finding other people like you. Not everyone who has money hangs with “the dynastic wealth crowd.” (I have inherited money but I wouldn’t even know where to go to specifically meet other people who do.) I don’t know where you live, but in the Bay Area there are a lot of young dot-com millionaires and they are casually accepted in many social circles that aren’t about country clubs, yachts, etc.

    If you have hobbies or work-related interests, especially ones that can cost some money to pursue but that aren’t limited to the rich (e.g., photography but not polo), you might try meeting other people that way. Through a hobby you meet other people with at least some money, who also have stuff in common with you.

    I’m emphasizing meeting people with some money because in long-term relationships, it matters a lot that partners’ attitudes about money match. That doesn’t mean their level of wealth has to match, but some parity helps.

    I wonder to what extent keeping a second apartment represents missing aspects of the “not wealthy” lifestyle you used to live? There are probably less deceitful ways to get some of that back in your life.

    For Kate (https://captainawkward.com/2012/07/07/292-wealth-massive-insecurity-are-messing-up-my-love-life/#comment-15765):

    If you’re concerned about what your friends think about your money, and about your buying things for them, ask them how they feel and what they prefer. US culture teaches people that it’s bad to ask each other about money, but learning how to have those conversations with a person is part of learning how to be friends, and it feels so much better to have those issues open for discussion.

  29. My partner makes more than I do. Not as much as when we met, but he does.

    On our first date, we went to the San Francisco Exploratorium. I think he bought the ticket, it made me feel a bit uncomfortable, even if it was only around $14. I’ve always been one of those people who feels the need to do my fair share of things (including splitting the bill). We ended up having dinner, and I think we probably split it. Needless to say, the next few times we saw each other, we went back and forth over who paid. It wasn’t as if we were going on extravagant dates, but when you’re a PhD student, it can start to wear you down a bit. I’m not sure exactly when it came up, but somehow the topic of paying for a meal came up. I told him that I felt bad because I wanted to do my fair share of paying for things so as not to put the burden on either one of us. He told me that he felt bad because he knew he made much more than I did, and he could afford to spend the money on these dates (I lived in Santa Cruz, and he lived in San Francisco, so we only saw each other on weekends), and he didn’t want me to overextend myself. Also, since I was driving up there, it put a bit more financial burden on gasoline, so he really wanted to do this.

    Honestly, I’m glad we had the conversation, because then I really didn’t feel bad about him paying for more things that I did. He was up front with me that he liked me, and he wanted to spend time with me, and I was up front with him because he knew I wasn’t trying to take advantage of the fact that he had more money than I did. (Which to be honest, wasn’t something I was really even aware of until then, I really just enjoyed spending time with him.)

    I think honesty is best. Even if it’s not right away. I mean, you can go on dates that aren’t extravagant and involve taking people back to your place until you feel comfortable talking about the money situation. I think you’d be surprised how many people may not even really care as long as you aren’t going out of your way to try to seem really poor (having another apartment and the like) just to keep out golddiggers. Maybe I just got lucky, but I think going slow is probably your best bet in these situations.

    1. Similar to my (now) husband and me: he likes paying for things if he can. Early on he told me that he enjoys doing it for friends, family, people he cares about.

      I’d certainly enjoy that too if I had any damn money, so I understood. I’m unemployed and have been for over 6 months now, and I do tend to feel bad about not contributing financially at all. But I make tasty foods, and take care of most of the chores (which is kind of weird for me, being a feminist and a housewife, but that’s besides the point). We love each other for ourselves, not earning power.

      1. I was unemployed for nine months after I got laid off, a few years back, and this was my exact situation. My husband is currently unemployed, so this is his job! We refer to it as taking a shift at being the “house spouse”. It’s a rough gig, mentally and emotionally, especially on the financial front and feeling like you’re contributing enough. You have my deep respect!

  30. I’d like to give a small example of how I’ve handled income inequality. My boyfriend earns more than me, not crazy amount more but enough to be noticable.
    Most of the time it makes no difference because the things we enjoy don’t cost very much – walks in the park, BBQs, drinks with friends, evenings in with a dvd. But we do both like good food, and occasionally he will suggest going to a restaurant that on my own I would not be able to afford. The first time this happened I said I was worried about how much it would be, and he told me that he would like to treat me because seeing how much I was enjoying myself would make him enjoy his evening so much more. That helped me to relax and have a good time, and I made sure that I paid the bill the next time we ate out somewhere that I could afford.
    So the relationship isn’t reciprocal in terms of how much money we spend on each other, but I think it is reciprocal in terms of gestures.

    So I would suggest to the letter writer that if you want to do something extravagant for a date or partner try to find something you think she will enjoy, and then ask her about it beforehand to see how she feels. Also give her space to make some kind of gesture in return even (or maybe especially) if it doesn’t have the same monetary value.

    1. Kudos to your BF for having a good way to make you feel okay about the times when he picks up the check for something extravagant (or out of your price range).

      In my (admittedly limited) experience, stuff like this will continue to come up for LW, even if he gets in a better place about it himself. I think it would be helpful for him to work on a “vocabulary” of things to say when the wealth disparity might otherwise get in the way of a comfortable evening or an easy friendship. There are good ways to say “It doesn’t matter” and “I don’t mind” that really will put both parties more at ease.

      For the other person’s part….I am often at a loss for what to do as a thank-you or gift for a friend whose situation allows her to provide herself with any item or comfort she might want. Just about anything I could afford to buy, she already has (or, more accurately, has a better version of). But you know what gift she loves? The thing she can’t buy, that no one else gives her? Mixed CDs. They take me enough time (because I seek out new music for her, and futz about song order, etc) that I feel like I have really given her a significant gift.

  31. I feel like, after reading though the comments, that many people have had negative experiences with friends and significant others who used money to manipulate, belittle, and otherwise harm. But I’m left wondering if the money in some of these situations isn’t a red herring — in other words, would this person have found some other stick to beat their “friends” with if income were equal?

    Having said that, income disparities, especially in romantic relationships, can cause real problems, which has been addressed pretty well in comments. Add to that the ways in which income and wealth intersect other oppressions, and it can get real messy real quick. I think the comments do a good job at addressing these, so I just wanted to throw in my two cents to the LW about the whole “fake apartment” thing.

    I think the reason many people are reacting so badly to, and are fixating on, this portion of the letter is because the reaction is totally out of all proportion to the issue the LW is experiencing. And the reaction is manipulative and scary, and angering on the level of “you chose WHAT to do with your money???” LW, I would ask you to reflect on why this elaborate French farce-style “solution” to your problem seemed like the most logical choice. What other ways to solve the problem did you consider, or try, and how did that go? Other people have already asked this, but really — what was the outcome in your fantasy of “the big reveal”?

  32. LW – I wanted to say something about the apartment issue, you can date people and not bring them back to your apartment. You can meet them out or hang out at their place until you feel comfortable having them over.

    Also, if your apartment makes you uncomfortable, it might be that you *want* to be the person with the smaller place. And you can be!! I know when I first moved out, I did everything kind of like I had seen my parents and their friends do it. I kept house in the same way, I decorated in a similar style, I even bought the same groceries that I had grown up with. And somewhere along the way, probably after throwing away my gagillionth box of stale cereal, I realized that I don’t like cereal, and that led me to realize that I didn’t like a lot of the other things I was doing either.

    All to say, maybe there is a way to build a life in an apartment where when people visit they see you and the kind of life you live and they don’t see what things cost.

  33. Ten years ago, two elderly childless relatives died, and I inherited a lot of money.

    It wasn’t the kind of inheritance that means I never have to work again. But it meant I could buy a nice house, no mortgage, and still have a substantial amount to sock away in savings for a rainy day, and that’s what I did. Suddenly, a lot of the money worries I used to have just up and vanished, and this was great. (It was also disturbing, but it was great.)

    It meant I could work part-time for a while and not worry, because, no mortgage. It means I can contemplate losing my job (which could happen this year) and not worry too much, because, no mortgage.

    I also have a job which pays me several thousand a year more than the minimum amount it’s been calculated an “average family” needs to live on. I don’t have children. I do have a partner, but we don’t (yet) live together. (Why we don’t live together yet is complicated but not relevant to this story.) She earns ten thousand a year less than me.

    My partner and I met two years ago this August, we’d been going out for a few months, we knew there was an income disparity (but I don’t wear expensive clothes or own flashy gadgets – it’s not a “concealing my wealth” thing, it’s a “Geeze, what kind of people spend THAT much on a pair of jeans” thing), and then she asked what-I-think-of-as THE QUESTION “What’s your mortgage? Or do you rent?” and I thought, okay, what I usually tell people if they’re being nosy is the true-but-misleading “I have a small mortgage” (my former mortgage provider continues to store the deeds to my house for free so long as I have the tiniest mortgage with them – so small there’s no payments due).


    This wasn’t someone being nosy: this was the woman I wanted to be with. I wouldn’t have lied to her about anything important (I might say “I don’t want to talk about that” but I wouldn’t lie) and the “I have a small mortgage” is deliberately deceptive because most people think of “small mortgage” as in the low thousands, not as a two-figure number.

    So I told her, look, this is something I don’t tell most people because it feels like shameless bragging, but you’re not “most people”: I own my house outright. And I explained to her how that had happened. And she was like “That was like you won the Lottery! Do you know how LUCKY you are?” and I said yes, I did know. And I do.

    In a sense, she hasn’t gotten over it yet. Why should she? It’s not something I’ve got over yet. Occasionally she still brings it up. Not resentfully (at least, I don’t think so) but often enough that I know it’s something she thinks about.

    There is no simple way to resolve the problem of one half of the relationship having a lot more money than the other half.

    (ANY kind of relationship. I’ve lost at least one friend because I leant her the money to pay her rent, she couldn’t pay me back, had to quit her apartment anyway – and I’m pretty sure is likely never to get in touch with me again because she’s embarrassed that she owes me a substantial amount of money and I don’t know how to resolve that. I don’t lend people large amounts of money any more.)

    We talk about doing things and going places and we get explicit about who’s paying for what and how we feel about that. We discuss how to resolve things. We talk a lot. Both of us want to be together, so it’s basically just a problem to be resolved with mutual empathy and honesty, which is exactly as difficult as it sounds.

    But to the LW: “problems with being awkward and feeling inferior and not being able to get laid” – well, I had those problems before I inherited the money, and I didn’t expect those problems to go away just because I’d had rich childless relatives who had unexpectedly decided to leave me their money, and I was totally right, it didn’t.

    On the other hand, it did make paying for therapy much less stressful. That’s not a joke. If you feel inferior and awkward and are sure this is what is stopping you from getting laid, I totally recommend shopping around to find a good therapist: you may find online dating sites are good too. Work at being completely honest* in your personal profile and read the Captain’s advice on how to write good dating-site messages to women you think sound interesting.

    *Completely honest* You do not have to say upfront “I have loads of money! I’m very wealthy!” any more than you would say (I hope) “I have a really huge penis!” or “I’m incredibly handsome!” Just … don’t lie.

    My partner and I met online via a dating site. In a sense “money helped me get laid” because she still gets smug over how I’d paid for a year’s subscription, while she was still in her first free month and never paid them anything.

    1. This is a lovely comment. I think you and your gf sound really cool and like you are dealing with a tricky subject with sensitivity and compassion.

      LW! Do like this!

    2. Regarding lending large amounts of money: it seems like the “standard” advice column take on this is to figure out whether you can afford to give the money as a gift (and whether you want to) and if so, do that. If not, refuse.

      I have a really fraught relationship with my dad when it comes to money. Basically, he cannot be trusted to keep his word regarding monetary issues. I actually didn’t speak to him for several years because of a specific thing he did, which I won’t go into details because I’m over it. After a while I started to feel that I could have a relationship with him again, but I just would not expect him to ever be reliable or keep his word regarding money. And I would avoid putting myself into any situation where it would cause me major problems if (when) he acted unreliably about money.

      Some time later, he asked me for a loan because he couldn’t cover his rent. I was very uncomfortable and I told him I would think about it. After thinking it over, I decided it would be only a minor inconvenience — one that I could live with — to just give him the money. So I did, and I decided that I wouldn’t ever expect to get it back. Of course he claimed he was going to pay me back and of course he didn’t.

      A few months later I lost my job. Right after that I had to do some major car repairs, which I was able to afford out of savings, but it sucked on the heels of losing my job. I complained to my dad, mainly to vent, and he suggested that if it would help he could pay back the loan. I said yes, that would help. Of course he didn’t do it. I felt myself starting to get annoyed, but then I had to remind myself of the requirement I had discovered for getting along with my dad: Don’t expect him to keep his word or be reliable about money, because he won’t. It still kind of sucks? But it’s not the cause of my financial problems. (And if he ever brings it up to me again, I will tell him flat out that him making promises he doesn’t follow through on damages our relationship and please stop doing that.)

      I guess the point I am getting at here is that it’s the expectations that cause the tension. So, for people who can afford to help out their friends and truly don’t care about the money: maybe just tell them that it’s a gift, not a loan. I did that once, too: I gave someone money after her husband dumped her and she was scrambling to try to get set up in new housing. I told her that if paying me back sometime would make her feel better that was fine, but I considered it a gift and did not expect to be paid back or care if she couldn’t/didn’t. That seemed to work fine.

      I guess maybe it wouldn’t work in all situations, but, maybe some? One can hope!

      1. “Regarding lending large amounts of money: it seems like the “standard” advice column take on this is to figure out whether you can afford to give the money as a gift (and whether you want to) and if so, do that. If not, refuse.”

        I have a couple letters in the hopper that could be answered this way – give it freely as a gift or not at all.

  34. I just keep staring at the “fake apartment” bit and I can’t even. Wowzers. I think the #1 symptom of the economic mental divide here is that while I can understand the impulse to keep all my real-self emotional stuff under wraps until someone proves they like the REAL ME (and I am pretty sure there have been any number of CA letters on that topic), the ability to casually enact that on an apartment-renting scale just makes my jaw drop. WOWZERS.

    LW, I’m not going to say “I wish I had your problems” because, no, I don’t. Your problem isn’t the money, it’s the sense that the other things you can bring to any kind of relationship aren’t as important as X. In your case, X is the fact that you can bring more financial muscle to bear than most people, but many people have values for X:

    “…the fact that my father is a congressman who likes to do favors for my friends.”
    “…the fact that I can talk my way into any club, ever, and bring my friends with me.”
    “…the fact that I work at a magazine and know a lot of models.”
    “…the fact that I am the world’s best cook and like to cook for my close friends.”
    “…the fact that I am a policeman and can make their parking tickets go away.”
    “…the fact that I am really, really funny and am a freakin’ scream to be around.”
    “…the fact that I am really low-maintenance and cool and together.”
    “…the fact that a movie star is my cousin and sometimes he/she hangs out at my house.”
    “…the fact that I am really easy to talk to and always listen sympathetically.”

    Any time you feel that X is more important than all your other qualities combined, and/or that all your other qualities are being merely tolerated because of X, that SUCKS, and I’m so sorry. Some times we feel like this because we’re insecure! Sometimes we feel like it because it’s happened before, and that sucks WORSE! All of these things are awful, and are big things to deal with.

    However, that leads me to this:

    I believed that money would solve all my problems with being awkward and feeling inferior and not being able to get laid, and it did help with a lot of those things. It has made finding actual love and good relationships much more difficult.

    Hold up, you’re skimming over something major here. How did having money help with a lot of those things? Because there’s “I have come to peace with my issues by spending a shit-ton of money on a REALLY GOOD therapist!” and then there’s “I have avoided dealing with my issues by throwing money at the symptoms instead of the root problem”, and I’m kind of wondering which one you are talking about. I’m kind of suspecting the latter, due to the fact that you have dealt with the pain of having had fake gold-digging assholes in your life by creating a secret-identity you with less-expensive tastes and a less-expensive apartment.

    I mean, dude, yes, it’s really tempting to just hide your X factor because you have a history of people only hanging out with you / dating you / banging you for that reason, but there’s hiding your X factor under a bushel, and then there’s scaled-up crazy-elaborate Batman-level* separate-apartment-renting. I mean, holy crap, you pulled a real-life La Cage aux Folles!

    There’s a lot more to “I have a second, less-expensive apartment” than “I write a second check every month and there is this other space that I may inhabit”, and you’re skimming over those, too. Not only “how much effort did you put into this?” but “how much of your real taste did you let shine through?” What books did you keep there? What pictures did you hang? What DVDs did you put on the shelf? What did you keep in the refrigerator? What went in the medicine cabinet? In short, just how much of your real self were you editing out, here? Because you seem to be very keen on the idea that people should like the REAL YOU, but how much of that actually made it through the filter into the second apartment? How much of it did your (ex-, I assume) girlfriend actually get to see?

    Let’s face it: the REAL YOU now includes “has money”, and that impacts the way you think. You tried to manage other people’s reactions to you so that you could avoid negative experiences, and it didn’t go well. Congratulations, you have discovered a great truth: people do not like it when you try to control them, and you get hurt anyway! So for God’s sake, stop doing that. This is no different than the old idea that a girl should laugh at all a boy’s jokes regardless of whether or not she thinks they’re funny, so that he’ll like her, or my thing where I pretend not to need things so that people won’t think I’m needy (and, I assume, FLEE THE GIANT NEED-MONSTER). Hon, I feel ya, but these things don’t work, they just leave us sad and alone because nobody loves the REAL US, and then we start to feel like the REAL US isn’t worth loving because clearly nobody does, even when, you know, we never did give them a chance to get to know the REAL US in the first place.

    You’re going to be vulnerable to hurt. I know. It sucks. It especially sucks when you have this huge resource RIGHT HERE and it feels like you could use that resource immediately to get the hell out of this itchy, nasty, scary-as-fuck feeling of vulnerability. But think of it this way: if you use your money to solve your own problems, people are going to think of you as someone who does that, and it makes it seem like that’s what they will get out of a relationship with you. If you are a person who does NOT use Deus Ex Chequer to solve your personal problems, that will go a long way toward making others see the other parts of you as more important. If you are good with dealing with emotions, other people will be able to look to you for support and advice. If you are good company under any circumstances, people will hang around to be around YOU, not to be around your credit card.

    There is a lot of advice here on the specifics of how to navigate this stuff in cross-tax-bracket interpersonal relations, and it all sounds good to me. You can do this! It is probably not a bad idea to get a therapist and get your head sorted out about; late 20s is, from my experience, when the heavy lifting happens in terms of Getting Yer Shit Together, so you are in really good company on that one. But you can do this. You can. And you are going to be okay.

    * Note: It is generally a good rule of thumb, in any circumstances, that when the answer to “Would Batman do this?” is “Yes!” then you need to BACK AWAY FROM THE BATMAN. A man who could end poverty in his city single-handedly and instead thinks that the best way he could fight crime is to dress up like a bat is not a sane role model for ANYONE.

    1. OMG, I love your Batman note. Both because the stuff that guy does is *really freaking weird* and should cause people to back away, and because I’ve actually never thought of the solving poverty issue but MAN THAT’S A BETTER CRIME-FIGHTING SOLUTION THAN A TRANSFORMING CAR.

      1. Yeah, I can see how, when the biggest thing that shaped the guy in childhood was the violent death of his parents right in front of him when he was too small and helpless to do anything, it would feel much more personally satisfying to set himself up in armor so that he was pretty much impervious and then go amongst the local criminals to kick ass, but acting like it is this big altruistic thing he’s doing for The People makes me roll my eyes so hard. It is not a solution to any problem except making him feel better, personally– the criminals don’t even stay in jail!

        See also: pretty much all of the “my superpower is that I am SUPER RICH!” guys on the DC and Marvel rosters.

        1. I love you, PomperaFirpa, and not just for the Batman thing – “Deus Ex Chequer” made me snort coffee out of my nose. And your advice is spot-on, especially about letting people see the REAL YOU.

          I saw a trailer for The Dark Knight Rises the other night, and it was all gritty and angsty and serious, and then I remembered it’s about a BILLIONAIRE IN A RUBBER SUIT WHO FIGHTS CRIME IN A FLYING CAR.

          1. Dude, I LOVE BATMAN SOMETHING FIERCE, because he’s smart, he’s analytical, he plans better than anyone, he works his ass off and is up against staggering odds and keeps going in spite of that. He is a non-superpowered dude in a world that has superpowered dudes, and he not only finds ways to keep up, he finds ways to take the superpowered dudes down if necessary. He is awesome!

            The problem being that if he took his head out of his ass and applied his awesome in more useful directions, he could be happy and he could probably make a lot of other people happy. Instead, he’s stuck in this ultimately self-destructive, community-destructive, and ineffectual loop where no matter how hard he works, nothing ever gets any better for him or for Gotham. It’s so sad.

    2. This is a really good point — even if we ignore the hiding-my-wealth part of the Second Apartment Solution, a new friend or potential partner can get a lot of their sense of who you are from what they see of your space. Some of my first conversations with my husband were about the stuff in our dorm rooms — Are those your magnets on the fridge, or your roommate’s? Where did you get that cool poster? Who took care of your plants over winter break? Wow, that book’s cover is practically falling off, you must have read it a million times! The things you love enough to keep in your living space communicate something about who you are and what you care about — if the “living space” you’re showing people isn’t where you actually live, are they getting to see those actual glimpses of your personality, or are you also stage-managing that in some way? (And even if you’re being totally honest in what you’re displaying, how are you going to convince the person who’s just learned that you were lying about where you live and how much money you have of that?)

    3. For that matter, X can be “amazingly hot” (a common problem among Awkwardkateers, I’m sure) though that would be hard to hide.

      (Also, totally stealing “Deus Ex Chequer”)

    4. This was by far my favorite comment, thank you. I sort of responded to this in a couple comments below, but I wanted to reiterate that Batman is and always has been my role model.

      No one likes the real me and no one ever has. This was my first actual relationship with an actual person. I have never had anything more than a surface friendship or very casual dating thing. I think I love her, but I don’t really know because I’ve never experienced it. I learned early and often that no one wants to know the real me. If they did, they wouldn’t always cut me loose when I start to open up about myself and my life.

      I’m more messed up than my letter implies, but I didn’t want to go into all the details.

      1. Oh, honey. I think that of all the things you could have said, “Batman is my role model” is the most indicative of just how screwed up things are for you. Batman is a tragedy: a man who was broken in his childhood, and who, in spite of his massive wealth, in spite of all the single-minded effort he throws into it, can’t succeed at healing himself because he’s going about it in all the wrong ways– and who can’t even succeed at his stated task of fighting crime, because he’s using his money to fight it on the wrong end. Don’t get me wrong, I love Batman, but as a role model, he’s incredibly depressing because there’s no end for him. He’ll always be like this, he’ll always fail at his bigger goals, because he’s required to in order for the comic book to continue the story, and for DC to continue to make money.

        Batman’s life is always going to suck, due to authorial fiat. You, on the other hand, are under no such restrictions: YOU are the author of your own life, and you are capable of changing your life into a much happier story. I know it feels like you can’t, that the “nobody loves me” thing is a set feature of your life caused by you being broken and fundamentally unlovable, but it’s not, and even if it was, you could dramatically increase the number of people who love you by learning to love yourself.

        I say that like it’s easy, but I know it’s not. It’s a process, a long and difficult job that can take years– it did for me, and I still fall back into that pit whenever I’m sad, but now at least I have ladders to use to climb back out.

        I know you’re reading everyone who says “augh, you crazy and weird” and taking it to heart and thinking “yes, that’s right.” I know you’re reading everyone who says “you’re worth something, you can be okay, you can love yourself and others can love you” and thinking “no, you’re wrong, you don’t know just how bad I am.” I’ve been there. I know. And it’s okay. It’s okay that you hurt this much. It’s okay that you don’t like yourself. It’s okay if people think bad things about you. It’s okay. There is no “deservedness” factor for love and forgiveness and help. You don’t have to meet any expectations of hard work or lack of mistakes or inner worth or whatever. It’s okay. You’re okay.

        Do you beat yourself up for mistakes, for not being X or Y or Z, for being A or B or C? It’s okay. Let one go. Forgive yourself and let it flow away. When it comes back to eat your brain, repeat to yourself that it’s okay, and let it go away again. Relax.

        You don’t have to meet a certain standard for love. You just have to exist. I’m so sorry that things aren’t working out for you, that your inner jerkbrain and your past and the people you know have combined to make it look like there’s nothing left for you but to despair, but you are okay. You are lovable. I don’t have to know your past to know that; I don’t have to know what’s wrong with you; I don’t have to know what you’ve done or what you think or any of that. You don’t have to do anything, you don’t have to be anything: you are okay, you are worthy of love.

        Many jedi hugs, sweetheart. I know it hurts so, so much, and I’m so sorry.

        1. “Batman is a tragedy: a man who was broken in his childhood, and who, in spite of his massive wealth, in spite of all the single-minded effort he throws into it, can’t succeed at healing himself because he’s going about it in all the wrong ways– and who can’t even succeed at his stated task, because he’s using his money to fight it on the wrong end.” This could just as easily describe me, which is why I feel such a connection with Bruce Wayne. I actually considered changing my last name to Wayne many years ago… there’s that crazy again.

          “I know you’re reading everyone who says “augh, you crazy and weird” and taking it to heart and thinking “yes, that’s right.” I know you’re reading everyone who says “you’re worth something, you can be okay, you can love yourself and others can love you” and thinking “no, you’re wrong, you don’t know just how bad I am.””

          Confirmation bias is a lovely thing. I generally avoid making mistakes as much as possible, and I put a great deal of effort into completely avoiding mistakes that could be visible to other people. “I’m perfect and everything is great!”

          It is very hard to believe the notion that you don’t have to meet a certain standard for love when my entire life experience indicates the polar opposite.

          My knee jerk response to all of this is to say, “look at me, I’m successful! I’m perfectly fine because I am everything that Western society says makes a successful man!”

          1. I once knew a woman who changed her name to match her favorite character from a musical. And “Wayne” is a pretty good name. So, yeah, I hear you on that.

            For the record– see my comment above re: Batman. There are SO MANY WAYS in which he is so completely bloody awesome I can’t even stand it. So smart! So detective-y! So good at turning overwhelming odds into victory by being smart and detective-y! Oh, God, I love me some Batman. He is awesome. And if his story were a novel, instead of a comic book series, all those things could work together to let him stop hurting, and to get over his past, and to connect with other people, and to become the true savior of Gotham.

            Batman’s problem isn’t that he is unlovable and unfixable and permanently broken. It’s that he’s in a comic book that depends on him being broken in order to continue having him be Batman, in order to keep the story going the way people like it, and to keep making money. You could be better than Batman, because you don’t have that authorial fiat over your head. (Much as it feels like it. Oh lord, I know that feeling.)

            I generally avoid making mistakes as much as possible, and I put a great deal of effort into completely avoiding mistakes that could be visible to other people. “I’m perfect and everything is great!”

            Hello, my fellow perfectionist! I thought I recognized you. Yeah, me too, to all of it. The black, icy terror that fills me when I make a mistake– I think you know that one. That sense that oh, no, I’ve done it wrong, someone will see, someone will know, and they’ll judge me, and I’ll be found wanting, and any sense of acceptance I’ve managed to scrape together will prove to be a sham. You know that one? Shake hands, my friend.

            I’ve spent so much of my life trying to be perfect. It has mostly led to me being frozen in place, afraid of making a move lest I make a mistake, convinced that I have to be instantly good at everything I try, so I never try anything new because people might see me being bad at it and because– worse– there’s the possibility that I might never be any good at it, even if I love doing it. It makes it hard to meet new people, because I spend so much effort trying to make sure they see the best possible me that then we don’t connect at all even if, it turns out, we have a lot in common.

            It’s possible to get past that. It’s possible to get over that. I know. It’s terrifying, and it goes against everything we’ve learned in the past, to stop putting on even more layers of armor and maybe even take some off. At some point, I hit a point where I was more afraid of never connecting to people than I was afraid of being hurt by trying and failing, and things changed (slowly, painfully) since then.

            It is very hard to believe the notion that you don’t have to meet a certain standard for love when my entire life experience indicates the polar opposite.

            Holy shit, don’t I know it. I think I have about a dozen t-shirts from that particular ride into hell. It sucks! But, yeah, that’s how it works. People love each other in spite of all the other person’s faults, in spite of all the dumb shit the other person does wrong, in spite of all the ways that person doesn’t measure up.

            If you’re anything like me– I think you might be– then the ways that you expect to be measured are the ways that you measure other people. It’s hard for me to see a friend who needs help and not think “really? you did that to yourself, what the hell did you expect? you need to put some effort into it if you expect any help from me.” But if I let go of that, and just say “my friend deserves help because my friend needs help, period, end of story”, it feels SO GOOD in my head. It feels amazing to let go of all the pressure of judging (holy crap, have you seen how people dress? that alone can use up most of my emotional energy before I even get to the office) and to just… not have to do that. To let it be okay for other people to suck. And the more I feel like it’s okay for other people to suck, the more I can feel like it’s okay for me to make mistakes, like it’s okay for me to not measure up, like it’s okay for me to not immediately be a top-notch performer at any new thing I try.

            It helps. Bit by bit, it helps. And the more emotional energy I’m not spending on judging other people (seriously, have you seen how people drive? this is hard for me!), the more I have left to love myself, and to love others.

            The people who have messed with you and who told you that you had to be THIS HIGH to ride this ride, are wrong. There is no entrance exam for being worthy of love. I know you don’t know me from Adam, and I’m some dork on the internet who doesn’t know anything about you, but I’m about ten years older than you so let’s just call me one of your possible futures. You can get to this place, emotionally. I promise you.

            My knee jerk response to all of this is to say, “look at me, I’m successful! I’m perfectly fine because I am everything that Western society says makes a successful man!”

            And you are! And that is awesome. I could tell you that being a success means that you must have all sorts of other good qualities and that this means that you are worthy of love! But you were worthy of love before you hit all those “successful man” markers, and you are worthy of love even without all the things that made you successful. That you haven’t experienced love says more about the people around you than about you.

          2. Mr. LW, in reply to your comments that you identify with Batman and have a soft spot for children’s charities, I wonder if you have ever done any volunteer work for a charity? You wouldn’t have to reveal that you give money to the charity also. One thing that’s good about Batman is that he tries to help. I don’t recommend the vigilante way of helping, but maybe there are other ways to help that would appeal to you.

            Also, how do you donate anonymously to a charity? I’d like to do that because I hate getting lots of begging mail afterward, but I don’t know how.

          3. @Firecatstef (downthread, but wp won’t let me reply to that post for some reason), re:donating anonymously: What I typically do is write them a check with a letter that says “Please credit this donation anonymously, and do not add me to any of your mailing lists. Thank you for all the good work that you do and I look forward to continuing to support [your organization] in the future.” That pretty much takes care of the begging letters, and I don’t mind getting thank-you-notes and donation reciepts for tax purposes. If you don’t even want those, I expect you can ask that too.

  35. I think that many of the small habits of daily life, are in fact crucial rituals for being part of a community. Everybody except the ultra rich and the ultra poor do stuff such as:
    * Separate recycling, take out trash
    * Shop for groceries
    * Maintain vehicle, or use public transit
    * Earn and use money (or earn it by proxy)
    * Comparison shop
    If you stop doing many of these things, you are likely either deliberately stepping out of society (monkhood, off the grid subsistence living), institutionalized, or attempting to join the ultra-rich class.

    So, since you said that you don’t want to date among the ultra rich, you should maintain or adopt the habits of the rest of us. Do your own shopping. Separate your recycling. Compost, if your location and municipality supports it. Buy nice things if you want and need them, but maintain them sensibly, yourself, and don’t dispose of them until they’re fully depreciated.

    You can have a nice car, a nice motorcycle, a summer house and a boat. You must sell them at market value, if they no longer amuse you. You can drive your whole pantry to the food bank and start afresh. You can’t ask your housekeeper to make it go away. You can have a cleaning service vacuum your floors once a week. You can’t have someone pick up your laundry off your bedroom floor daily.

    Being casually wasteful with stuff is like feeding bears. It’ll surround you with people who are in your life to scavenge your leavings. It may feel like a waste of your time to comparison shop, but the only way you can do business with honest people is to pay attention.

  36. I’m hoping this letter is a put-on, because SECRET APARTMENT is one of the creepiest things I’ve seen on Captain Awkward. On top of the deceit and manipulation, spending the equivalent of many people’s entire income on trying to trick girls into relationships…does not speak well to the LW’s character, to put it mildly.

    (I’m especially groaning at the “but I don’t know what else to do” part. You can NOT TRICK PEOPLE. Even people you want to date! Maybe even especially people you want to date!)

    LW, the impression I get from your letter is that you see your financial status as the most important and interesting thing about yourself, the thing that defines you. It sounds like your internal narrative goes something like this: “I was an awkward loser who couldn’t get girls, but then I made a bunch of money so I can Show Them All, especially the girls.” That’s a narrative that’s likely to attract people with unhealthy attitudes toward money (and girls) and scare away people with healthier attitudes.

    I suggest you change that narrative. Maybe to something like: “Thanks to some combination of hard work and luck, I don’t have to worry about money right now. That’s opened up a lot of cool opportunities, but it’s mostly only important to me and my accountant. I’d much rather think about…”

    And no more sitcom trickery!

    1. I do think it’s telling that where so often on Captain Awkward the LWs will come back in the comments to either thank everyone or give an update or more context or SOMETHING, over 100 thoughtful replies later this LW hasn’t shown back up once. That makes me think that on some level he knew exactly what he was doing, and was surprised at being called out for what is truly fucked up about his whole situation.

      1. Not necessarily. He might not have checked in yet – maybe he’s hanging out in his massively gadget-ed apartment playing games online and drinking vodka because he just got dumped. Or is really busy at work with the job that makes him all this money? Maybe he has taken the advice and is packing up his fake apartment as we type.
        Or he might just not know what to say.

        1. I’m pretty sure that when I was the LW a long time ago, I didn’t check back in because I was so ashamed of having the problem in the first place I just took my advice and ran. I mean, not *far*, but I still felt like a screw-up.

          Healthy? God, no. But that’s how it felt. So I can feel for this LW if he’s like, “OKAY, LESSON LEARNED, MOVING ON.”

          1. Right, he’s under zero obligation to take the advice, read the advice, use the advice, or update us about the advice. Lots of different perspectives and opinions here. I’m definitely still processing them all and I’m just an audience-member to this dude’s life. He’s the real expert on his own situation.

      2. Hey Lucy (and others):

        The LW is under no obligation to take the advice given (all advice is caveat emptor, and he is the expert on his own life and can best tell if something will work) NOR under any obligation to report back. It’s always really nice to hear from people either publicly or privately if they feel like sharing, but it’s not a reflection on character if people don’t let us know what’s up. Some things don’t work, or take time to sink in. Come on, why would anyone come back if they think they’re just going to be made fun of for not coming sooner?

        This whole thread is really making me think about how I think about money, love, friendships, early stages of dating, etc. and giving me some new perspectives on how money solves some problems and exacerbates others for sure. (Come on, how awesome is it that an ACTUALFAX GOLD-DIGGER dropped by to tell us how it’s done?). I think shame kills real communication in so many cases, so LW, if you’re out there and still reading, you don’t have to come back ever. I hope you’re ok and really thinking about what makes you great and what makes you you.

        1. I definitely agree about the no obligation, but just wanted to say that it’s important to remember, LW, that money is not the only thing out there that makes people think “if I didn’t have it, nobody would love me.”

          Talents, intelligence, looks, ability to teach/train in something, ability to remember things, being funny and telling jokes . . . all of these are things that people everywhere struggle with on a daily basis.

          We feel like something defines us. Sometimes we don’t even realize that we identified so strongly to that something until it’s slapped in our face that someone doesn’t need us anymore for that aspect. I recently had to deal with the realization that I identified part of my value with my ability to help tutor other students in the foreign language I was learning (including my SO) But when my SO re-remembered an old study habit he used to use that worked, he didn’t need to study with me anymore. I was crushed and felt like he didn’t need me anymore. But my problem was with *me* . . . I had identified too strongly with that “talent.”

          What I think this really means is that we have to own all of our negatives as well as what we see as positives. We have to try to love ourselves for everything, and that’s really hard. It’s an ongoing struggle.

          But I hope it might help you to feel better to realize that you having money is just one of many things people think are worth more than “themselves.” Look at your quirks – look at what makes you interesting, but also think about your negativity. Look at it hard, talk to a counselor about it, and study how your youth defined parts of your life in ways that are now effecting you whether you are currently aware of it or not.

          If you lost all that money *right now* . . . who would still love you? Is there anyone you had before the money who was a good friend? How have your friendships and relationships that you had before the money (family, friends, exes, etc) been effected?

          I get the feeling that this self-isolation might be about more than merely “new money” verses “old” and that maybe he’s had problems with money outside of romantic relationships.

          For everyone saying the fake apartment was creepy, yes, it seems creepy and controlling. But also please keep in mind that if a person is panicking (and believe me, from personal experience, it is possible to endure constant states of panic for months if something huge is stressing you out) it is far too common for all sense and sanity to depart when it comes to decision-making. He might have truly felt that he was unable to *see* any other answers. He might have been so stressed from the new wealth he now had and his uncertainty of what it meant about *him* that his mind was so over-taxed that he literally *couldn’t* think clearly.

          Stress does terrible things to our brains. And that’s not a diagnosis, lol.

          1. Just want to add: please, LW, I strongly suggest that if you have any people who loved you before the money and love you now, go to them and get some comfort. You of course don’t have to tell them anything, but they might be able to help you anchor yourself.

          2. Thank you Dana. Part of the problem is that there isn’t anyone. I loved the Batman comment because I have always looked to Batman as a role model since we are both orphans. I only ever read Batman comics, and I dreamed of the day when I’d wealthy like Bruce. If I lost all the money now no one would love me because no one loves me with the money. The money just lets me pretend that people around me do actually like me. This was my first real relationship and like I do with everything I ruined it. The one thing in life I seem capable of doing without screwing it up is making money.

          3. I had a strange feeling it might be this.

            I guess I will tell a small story myself, so you might know you’re not alone!

            My parents got divorced when I was an infant – maybe 1 year old at the latest – because my mom kicked my dad out. Strange, since she was the one doing all the heavy drugs. Yeah, I’m probably a crack-baby. It probably explains my ADD, clinical depression, and some other issues I have that my other family doesn’t have. I’m lucky to be alive, let alone sane.

            But when my dad got custody, it wasn’t all great either. Turns out he’d done lots of drugs with my mom (and other people before her) so his brain isn’t all there either. (And I was secretly told that his birth was difficult and might have given him brain damage)

            My dad basically is an 8 year old in a grown man’s body. And so I grew up really fast. And this scared people. I’d go up to smokers, all of 6 years old and say (with a no doubt creepy voice) “You’re gonna die if you don’t stop smoking.”

            When I was 8, my dad sent me for a month to a Children’s Hospital for them to try to “examine” me long term. I thought it was 4 months (it felt that long) and I *knew* as only a child can be certain, that it was a mental hospital for crazy children. Why? they took away all our scissors and nail clippers, and all the other kids were *really* out there. And if you acted bad and started freaking out . . .they’d drag you off and we NEVER SAW YOU AGAIN. We were convinced that the bad kids were put into padded cells, never to see the light of day again.

            Ever since I was conscious, I felt I was basically an orphan. I’m not sure what caused your state of being orphaned, but maybe knowing somebody understands might help. It sucks being on your own. I’m not sure whether anyone can compare lives and say which sucks more, but I do know that you are NOT worthless. Maybe you should try making some internet friends? Your wealth will mean less to them (usually.)

            A lot of my friends are very well off. A lot of them are poor as dirt. My in-laws are pretty rich themselves. Everyone else here is correct when they say that the money is just another layer of armor. You need to find value in yourself.

            I suggest online friendships *as well as* trying in real life. Many people who feel awkward in real life have tons of friends online, so you won’t be alone in that feeling that maybe, in real life, you have something about you that screams “bad!” (A lot of people feel just the same!)

            I think that maybe, if you’ve had trouble explaining to your counselor, maybe you should print out this column and take it to her (or send her the link – wow, we’re in the future!!)

            Also, I worry about you! If what you say is true, then you are no doubt feeling very isolated right now. The internet is really great in that it can let us connect with others even when we feel the most like hiding. We can connect while still remaining “concealed”. Do you have a community? If not, then maybe try to find one that shares your interests in hobbies or something. You must have *something* you could do (even if you don’t do it well) such as playing video games or roleplaying or something.

            Long after the traffic on this thread has faded, I think I will often be wondering how you are doing . . . If there was a way to share my email that was private, I would. I’ve been suicidal before. I hope you are not, but wouldn’t blame you if you have entertained such thoughts. I hope you remember that all of us here care about you, so clearly there’s something very worthwhile that you just can’t see yet!! *BIG HUGS* I’ll be thinking of you.

    2. LW, the impression I get from your letter is that you see your financial status as the most important and interesting thing about yourself, the thing that defines you.

      THIS. Yeah. This worries me, a lot. Like “I wasn’t interesting before, and then I got all this money, and now I’m still not interesting but the money is WAY COOL.” Just. Augh. Yeah, yeah, money is totally fascinating and blah blah blah whatever, if you are concerned about not being interesting, BE MORE INTERESTING. Embrace your inner awesome!

      As far as I’m concerned, there are only good things about money: it gives people the resources and space in their lives to a) get a great therapist and get their head straight and b) spend time doing the things they love. DO THE THINGS YOU LOVE AS HARD AS YOU CAN, LW, AND YOU WILL BE FASCINATING. Not to mention, you will have a more fulfilling life, and have more fun, and find people you click with more than OMG SO YOU HAVE MONEY? I LIKE MONEY! WE HAVE SO MUCH IN COMMON!

      The more I look at this problem, the more it is every late-20s problem: “Suddenly I have to find people I have something in common with, but I’m not in college anymore and I can’t just hang with people in my major, what do I doooooo?” The money is a red herring. The Batman apartment, while wicked fucked-up, is a red herring. BE YOURSELF, NOT YOUR MONEY. BE A GODDAMN ACTION VERB INSTEAD OF AN ADJECTIVE. Problem solved, no need for a Batman apartment.

      1. People, in an individual sense and as a whole, are interesting. We have whole branches of science devoted to the study of people! That wouldn’t be the case if people were boring.

        The thing is, almost everyone I know that thinks they’re not interesting actually is very interesting. Except. You don’t have to live like the protagonist of a story to be interesting. You just have to be YOU.

        No, you aren’t boring. No, you aren’t dull. No, that story about how you went to the grocery store the other day isn’t prosaic and uninteresting. Your friends probably want to hear that grocery store tale.

        In short, I agree.

  37. Something that didn’t come up at all: LW…you could just live in the fake apartment for real, you know. If you’re worried about looking like Richie Rich, maybe you could skip the creepy false face and just live nicely in a smaller place??

  38. I have read all of the comments, and I do appreciate all the advice. There is a lot here to process and a lot to the situation as a whole. I wasn’t sure if I was supposed to turn this into a whole psychotherapy couch session or something and talk about all the past life events that made me think of this as a good idea. I had actually written a comment last night in response to the Batman comment because Bruce Wayne is basically my life long role model.

    I have never felt that I have value as a person, and this notion has been reinforced by the world at large forever. I am an easy target for people looking to get something, because no one has ever liked me as a person. I have always given people the benefit of the doubt but if people can’t get something from me, they don’t want to be around me. I started using money to buy friends and lovers, but it does not actually give you a real relationship. I had hoped that by hiding my assets to a considerable degree, I would be able to have the surface level confidence that being well off provides, without the giant bullseye on my back.

    I was hoping that she would see that I did the whole thing for a good reason and not to be a creepy guy. I want to love and be loved. I wear my money like armor. Is it better to be used and envied than neglected and ignored? I think so.

    I didn’t want to give people the idea that I haven’t been reading these and that I don’t appreciate the advice because I do. I also accept all the consternation and disgust. My problems are much deeper than just this instance of craziness, and I see a therapist twice a week.

    1. Hold up there, Bruce. Can I call you Bruce? Great.

      I have never felt that I have value as a person, and this notion has been reinforced by the world at large forever.

      That is some massive jerkbrain thinking you’ve got going on there, friend. It’s a vicious, self-reinforcing cycle when you don’t believe you have value to other people, or that no one loves you. The first person who needs to love you is you. Yeah, I know, Bruce, that sounds like lame hippie-dippy stuff, but if you’re constantly thinking “of course no one loves me, I mean, LOOK at me!” then that’s a big frikkin’ problem. Let’s see how self-loathing reinforces itself when you try to make friends!

      You: Hi!
      Potential New Friend: Hi!
      You: You seem nice!
      PNF: Oh, I’m okay.
      You: No, you’re amazing. So amazing, that you shouldn’t hang out with me. I mean, I totally suck.
      PNF: ??? Oh… kay? I mean, I only have your word to go on right now, so I guess…
      You: *sigh* I knew you’d see how much I suck. No one likes me.
      PNF: Well, I thought you were okay, but if you think you suck I guess I’ll go hang out with other people.
      PNF: But I have good friends already. I’m gonna go hang out with them now.
      You: 😦 No one likes me because I suck.

      You’ve got so much armor protecting your heart that no one is going to get in without a fight. People want to get to know you, but they don’t want to have to fight to get to know you. That doesn’t mean that you’re without value, or that people won’t love you, it just means that people are lazy. You’re going to have to be just a skootch vulnerable instead of pre-rejecting yourself for people, Bruce, and I know that’s going to scare the beshits out of you.

      So step one: Be kind to yourself. Don’t say or think anything about yourself that you wouldn’t say about someone you loved. The mean jerkbrain is wrong, and you have to use your smartbrain to counter it. Your therapist is probably trying to help you with this.

      Step Two: Go to some activity with other people where your only goal is to do the activity and meet the people. Board game night at a local bar. Trivia night, try to join a team (heck, offer to buy a round for a team to let you in, congratulate the winners, and/or console the last place team). Sailing meetups. Team sports. Social dance. Take up knitting. WHATEVER. Go do something where people are, and just practice getting to know people. Important note: I did not say “make friends.” I said “get to know people.” Some of those people MAY become friends, but most of them you’ll never see again, and you need to get okay with that. But the more people you meet, and the less pressure that you put on yourself and them in your interactions, the more likely you are to have some true friends.

      I think it’s more important for you to have friends before you find love. Have some generosity of spirit, Bruce. Take off the armor, the tux, and go out on the town. Ask other people about their lives and loves. See what stories other people have. And tell hate to take a hike.

      1. You: Hi!
        Potential New Friend: Hi!
        You: You seem nice!
        PNF: Oh, I’m okay.
        You: No, you’re amazing. So amazing, that you shouldn’t hang out with me. I mean, I totally suck.
        PNF: ??? Oh… kay? I mean, I only have your word to go on right now, so I guess…
        You: *sigh* I knew you’d see how much I suck. No one likes me.
        PNF: Well, I thought you were okay, but if you think you suck I guess I’ll go hang out with other people.
        PNF: But I have good friends already. I’m gonna go hang out with them now.
        You: No one likes me because I suck.

        Oh dear God, I spent so many years of my life doing this. It really is a nasty self-perpetuating cycle.

        And, yeah, there’s a really variable success rate at turning “people I met” into “people who are friends with me”, and I spent a lot of my life thinking OH GOD SOME PEOPLE DIDN’T LIKE ME CLEARLY THEY HAVE SPIED THE TERRIBLE CESSPIT OF MY SOUL instead of thinking “huh, well, guess we just didn’t click, it happens, MOVING ON NOW.”

        LW, I know it is hard advice to hear in the midst of sad miserable woe, but do things you like, that make you happy. If you don’t know what those things are, try a lot of things until you find some. Note that I did not say “that you’re good at!” because those two things are not the same. You don’t have to be awesome at something to like doing it– and that’s something that most of us forget when we’re shamed out of doing things we like, back in elementary school. If it gives you joy, do it.

        And… help other people. I don’t know about anyone else, but this always gives me a little boost on bad days. I think the part of humanity that was programmed to promote community is designed to goose our serotonin levels as a reward for doing community-based things.

    2. I think that a pretty big theme in all the Captain’s Advice is that even if you are a terrible person now (and I really have no idea whether that is true or not) you don’t have to remain one forever, people grow and change all their lives. I think one thing that is really holding you back at the moment is this self story you have about how lame you are without your money. Money can be awesome, it’s true, but it’s unable to buy you self worth, which is, from what you are saying, what you kind of hoped it would do. I recommend at this time probably not dating, because you need to work on like you before you will believe that anyone else does. So heres something to do, make a list about what you don’t like about yourself, do it over a couple of days if it gets too hard mentally, and once you are done, for each one write down a couple of concrete things that you could do to change that about yourself, and then do them, if you can’t think of anything for an item, talk to your therapist about those items. There will be some things on the list that you probably won’t do, but even then you have made a choice, and can say “yes I’m not super happy about that aspect of my self, but I have decided that in the end, I can live with it over doing what I would need to do to change that about myself”.

    3. LW, I am so very glad you see a therapist twice a week. Go, you!

      I don’t think there’s any advice I can give. I feel you’re in a morass of bad self esteem and a whole lot of feeling sorry for yourself, which is a pretty un-fun place to be. I hope your therapist is helping you and that you’re seeing the results of it, so that you can realize that the world is not so terrible a place and the people in the world are not all big using users who want nothing from you but your material wealth.

      Okay, wait, I do have a piece of advice: Bruce Wayne is a pretty terrible person. He’s a liar. He’s all surface, because underneath Bruce Wayne is nothing but Batman. Bruce Wayne uses women romantically to prop up his playboy persona, but he doesn’t let them get close to see who he really is. (Mostly. Except for all those women that do in the comics and movies, but who either die tragically or vanish. Or are Catwoman in New 52, but that’s creepy rewriting and has me making an ickface just thinking of it.) You may want to reconsider using Bruce Wayne as your role model, or at least think about his flaws.

      That said, I don’t think you’re a terrible person. I think you’re looking for something that’s within your reach, but I also think that, until recently, you haven’t realized the implications of some of your behavior.

      Changing yourself is a hard process, full of backsliding, sure, but also full of exhilarating realizations. I’ve been there. The results are worth it. Good luck!

    4. I wrote this whole comment about how you should invest your money (invest in your future security, invest in yourself, invest in your friends and family) and then I saw your response and realised that isn’t what you need. What’s hurting you isn’t your money – it’s how you feel about yourself.

      I want to love and be loved. I wear my money like armor. Is it better to be used and envied than neglected and ignored? I think so.

      Mr. LW (may I also call you Bruce?), you sound so sad. I don’t mean pathetic, I mean like seriously, deep down sad and lost, and that made me want to reach out and give you a hug. But your armour would get in the way. I think somewhere along the way you started to believe that if you kept wearing the armour, no one would ever be able to hurt you again – but now the armour itself is starting to chafe. It hurts and it’s uncomfortable and you want to take it off, but you’re scared because you’ll feel cold and unprotected without it, and may also have helmet-hair. But the armour doesn’t fit any more.

      What you were trying to achieve with your fake apartment thing was to find an answer to the question, “how can I make sure that I’m totally, 100% safe to take off my armour with someone who will never, ever hurt me?”, and the answer is “You can’t”. If you let someone get close to you, that person can hurt you. Sometimes they may love you like crazy and still hurt you, because life sucks like that. But loving people(not just romantic partners, but friends and family) and being loved in return is worth the occasional hurt, because it’s the best feeling in the world. And in time it becomes its own armour against the slings and arrows of outrageous fortune – they don’t hurt you so badly because you know you are loved and you have people to help you recover from your wounds.

      Batman isn’t 100% safe when he takes off his armour. Hell, he isn’t even 100% safe when he’s in the batsuit. He could stay in the Batcave and send out remote controlled gadgets to try to fight crime, but that’s hardly the most efficient or bravest way to be a superhero (no one is going to be impressed by Batman the gadget controller). Or he could build a batsuit made of solid steel, but then he wouldn’t be able to do all that running and jumping and climbing buildings he needs to do to save Gotham City, so he has to accept the trade-off between “protect myself enough so that I’m not exposing myself to stupid risks” and “be able to live out my destiny as the Dark Knight – which requires some flexibility in the suit design so that I can climb buildings and fight The Joker”. You’re hiding in the Batcave wearing a solid steel batsuit, my friend, and that means that you’re of limited use to the residents of Gotham. You need to be the hero of your own life, and that means opening yourself up to the possibility of getting hurt.

      Okay, I am going to stop with the Batman analogy now because dear god, me, enough.

      commanderlogic is right – you have to like yourself before other people will like you. If you don’t think you’re worth anything, you won’t have the confidence to attract others. I love the commander’s advice, because one of the simplest steps is just to spend time with people, get to know them and LISTEN to them without expecting anything in return other than a conversation. Ask people questions (reasonable questions!) about themselves and listen to the answers, then follow up with more questions about what they’ve just told you (“That sounds really fascinating – tell me more about X”, “Wow, you’re so lucky to have done Y – what was it like?”). Respond to their questions, but don’t commandeer the conversation. People like to talk about themselves, and they will like you for being interested in them. Then, before you know it, you will have made some friends.

      “Used and envied” versus “neglected and ignored” aren’t your only options, but I think that you think that they are. I can see how you’ve ended up where you are because things clearly have been bad for you for a long time, but you need to understand that it’s flawed thinking and you need to challenge it whenever you find yourself thinking that. I like this Mind article on increasing your self esteem as it has some good suggestions for how to challenge your negative beliefs:

      This probably isn’t what you want to hear, but I think you’re trying to run before you can walk if you’re looking for a romantic relationship right now. You’re not in the right place yet. If you start dating right now, you will end up sabotaging yourself and it will knock your confidence still further. You need to take care of yourself right now – that should be your top priority.

      How long have you been in therapy for? Have you properly opened up to them and told them everything you’re telling us about how you feel about yourself (and all the things you haven’t even told us)? If you’ve been seeing someone twice a week for a while and you’re not feeling different in some way, then perhaps this person isn’t the right therapist for you. But you need to open up fully – if you’re hiding things from your therapist then they can’t help you. It’s confidential and they won’t judge you. Close your eyes and jump right in. Believe me, it’s also amazing how liberating it can be to TELL SOMEONE all the worst things that you think about yourself, all the most painful, self-pitying, nasty, poisonous things that you have kept inside you for so long. Almost as soon as they’re out of your mouth, you can see some of them for the chimeras that they are, and the therapist will help you to work through the ones that have somehow hung on to their power even though you’ve dragged them into the daylight.

      I really wish you the best and hope that you can find a way through this. You are not unlovable – you are someone who has not yet found a way to love yourself. You will.

    5. Glad to have you check back in. I would expect that the candor of some of these critical remarks would make this tough reading. I admire you for sharing more.

      Here’s a suggestion that has nothing to do with your love life; it came to mind because you say you’re pretty disconnected and unappreciated. One of the ways you might be able to feel more connected, worthy, and appreciated is to start spreading that money around to local charitable causes. Your money can open doors for you; that may sound crass but it’s absolutely true. It is a valid, time-tested way to connect with people when you have $$ to spare.

      Start exploring local causes and non-profit organizations. Send a modest donation to some of the ones that sound most interesting to you. Get on their mailing list and you’ll start getting invited to their fundraising events (dinners, auctions, etc). Attend those, meet more people, get hit up for more money. You will not be ignored. I am here to tell you that there there are people and causes out there who need you and your money, who will get to know you because they want your money. That sounds distastefully like “gold digging,” I know. But guess what? This is the normal course of non-profit fundraising. Wealthy donors get used to this kind of thing. And the reason they tolerate it, as I understand it, is that it ends up being about more than just your checkbook. You may make some genuine friends, and learn of interesting opportunities to volunteer time, & feel a bigger part of important causes. You will be doing good along the way.

      There are probably numerous local organizations out there you are not aware of yet. They all need your money. Some need it more than others, some may feel more like a natural fit for you; it may take some time to find your niche. But I believe it’s out there, whether it’s an animal shelter, or a group trying to build a skatepark, or a children’s theatre troupe, or the homeless shelter, or a horseriding stable for disabled citizens. I say get out there and start changing the world, Batman. It’s okay to get your foot in the door with your money. It’s how people do it!

      1. Oh no, I say things to myself ten times worse than any remark here. I feel very awkward about donating publicly. I actually donate a considerable amount of money to charities because it makes me feel good, but I always do it anonymously. If it is a charity that benefits children, I’ll donate to it. I don’t have enough money to help every disadvantaged child in the world but someday maybe I will. I know what it is like to be a neglected child searching for help from someone, anyone, and receiving none. I just feel weird about people knowing I have a soft spot for children, because it would mean I might have to bring up why.

        1. I just feel weird about people knowing I have a soft spot for children, because it would mean I might have to bring up why.

          First, it’s awesome that you do this; I liked you before but I like you even more now. But let me assure you, having a soft spot for children means that you have a big thing in common with a hell of a lot of people, and everyone has a different reason for it, and nobody really wants to discuss why because most of us have that sympathy because of fucked-up things in our past.

          Thank you, by the way, for doing that. I’m in a strapped financial situation right now and it hurts my heart to have to say no to helping kids, but it helps to know that you do. Thank you.

        2. I’m going to suggest that you couple your monetary investment with a personal investment. If disadvantaged children tug at your heartstrings (as they do most people’s!), there are many, many things you can do that will help them AND help you. Kids will respond to WHO you are, not how much money you have. Pick one of your charities and ask if they need some help during their annual fundraiser. This could be signing people in at registration or running the baked goods booth. Or go to your local library branch and ask if they need someone to read during story time. Most reputable organizations will ask you to undergo a background check, to make sure you aren’t super, legitimately creepy (which I don’t think you are).

          I don’t think you have to explain your interest with reference to your past. I inhabit the non-profit world (I’ve worked at several and am on the board of others) and saying, “I want to give back to my community,” is sufficient. The focus is on the kids and on the future, not the story of what brought you there. Even, “I remember what it was like to be a kid,” would be an adequate explanation.

          It might help if you have a one-minute version, a five-minute version, and a half-hour long version of your life story. Believe me, most people only have patience for the shorter stories!

          You could not have picked a better cause to get yourself involved in. Disadvantaged kids trump everything–historic preservation, archival supplies for disintegrating film, spaying/neutering stray animals–kids are where it’s at. They are many, many, MANY programs around that would love not just your money but your actual physical presence. As long as you are willing to work, you will be welcome.

          I was once volunteering at an animal shelter and I was paired with the nicest lady. She was obviously well known to the staff. She knew where all the supplies were and how to calm the most frightened dog. She gave all the critters baths that day and she was covered in fur and scratches. I only knew her as “Robin.” The following week, when I got the newsletter from the shelter, I realized that the building was named after her. I was super impressed with that women because she really got in there and did the work. She didn’t act like she owned the place; she checked with the director before making decisions. But she was the heart and soul of that place. She had found her niche–the way that she was able to make a difference. She made MY day better as well as gave comfort to countless cats and dogs. You will get to know people like that and they will serve as models for you.

        3. Thank you for being a donor already!

          If you want to be anonymous to the public, organizations will comply with your request to not be named or listed in their materials. But you don’t have to be anonymous to the organization itself. You can be involved without wearing a big “I’M A DONOR” sign. And so what if you donate to children’s causes? That’s a common cause to be soft-hearted for; it doesn’t make you a target nor does it mean you owe anyone an explanation. Lots of people & foundations do “specialize” in their charitable focus because otherwise it’s too overwhelming to field requests and evaluate the worthiness of organizations. That said, organizations don’t know where else you have or haven’t donated (especially if you give money anonymously); they don’t know whether you have one favorite cause or ten.

          I see your charitable giving as an entree into being more involved. It gives you a really great opportunity to connect with people and to revitalize your sense of self-worth. Of course, you don’t need money to accomplish that, but in your particular situation, it may be the catalyst you need to overcome some of your doubts & concerns.

        4. Everyone’s given you really good advice–I just wanted to say that it’s okay to let people know you have a soft spot for kids. *I* have a soft spot for kids, and I not only had a good childhood, but I’m pretty sure I’m never going to reproduce. Most people have soft spots for kids. If (when!) you volunteer and someone asks, you don’t need to tell them things you’re not comfortable with. You can just say that you had some tough times as a kid, and you want to help others. Or if even that’s too much, just say that you want to help.

          You sound so alone and lonely right now, it breaks my heart. Could you get a pet? Would you like one? They’re not the same as a human connection, but they’re warm and fuzzy and they’ll listen to you and never judge. And some pets require activities that will let you meet other pet owners (which will normally just lead to a friendly “hi” as you’re walking your dog, or maybe someone asking you a question as you’re getting cat food from the store).

        5. Given the amounts of money it sounds like we may be talking about here, one option would be to consider starting a private foundation.

          One advantage of that is — well, aside from potential tax stuff and all that — is that it allows you to plan your giving so that you’re not just giving because you’ve randomly heard about a particular charity, you’re sitting back and thinking, “How can I give strategically to produce the best possible effects in this field?” (e.g. improving the lives of children in need).

          AND, very importantly, a foundation will involve other people (fellow trustees, financial advisors, maybe an employee or two) who are there to help you talk and think through all of this stuff.

          Which is a really good way to stop your relationship with money from being a crazy private thing that stays inside your own head where it can get tangled up with all your insecurities.

          And it means you’re not going to be thinking about money just in terms of whether it’ll make people like you or not, but in terms of the good you can do with it — and the good you do is not just about having the ability to write a big cheque, but to be thoughtful, to plan your giving, to develop knowledge about the field, to work with other organizations, and all sorts of other things. Which is something to be proud of.

          A foundation also provides you with an interface, so you can have more or less contact with the causes you’re giving to, and more or less privacy, as you need it. Which, if you’re prone to anxiety and stress, can be a very very good thing.

        6. I’m going to second the people who say you should try working directly with children, because… Batman needs a Robin. It is the best thing about him and what keeps him sane-ish. I really dislike Bruce Wayne but I love all the Robins and Batgirls. Now mind I’m not suggesting you pick a kid up off the streets and get them involved in dangerous crimefighting and hinky sexual overtones, just that you have one individual kid you care about who can care about you back. A million deaths is a statistic, one is a tragedy, yadda yadda. Knowing you gave enough money to charity to feed a dozen kids today is much more intellectual. Hanging out with one and having an ongoing relationship might help you more emotionally.

          (I am not actually mocking your comic book identification. We can’t always choose these things. Ask me about my love for Lex Luthor. Maybe someday I’ll be happy enough to be Kon instead.)

    6. I have never felt that I have value as a person

      Whoa back.

      I want to tell you a story.

      Years ago, in a Quaker Meeting, a Friend got up and talked about something his headteacher had said, in a meeting that he and other teachers were having about a really troublesome boy in a boarding school. The meeting had been going on for a little while, and all the teachers had had something to say. The headteacher sighed, the Friend said, and asked the meeting

      “Doesn’t ANYONE have anything good to say about him?”

      Then he clarified, “Seriously, ANYTHING. Does anyone have ANYTHING good to say about him?”

      There was another silence.

      “For example,” the headteacher said, “Did he brush his teeth this morning?”

      Well, one of the teachers had been supervising in the dorm bathroom and was able to say yes, he had brushed his teeth.

      “All right,” the headteacher said, “he brushed his teeth, that’s good. What else?”

      Given this lead, given permission to look for even the smallest good thing, all of the teachers – the Friend told us – had been able to find SOMETHING good to say about the boy.

      And the Friend said, what he had been thinking about this, in Meeting that morning, was how easy it is to look at the negatives, how difficult it sometimes is to acknowledge the positives.

      I do not believe that you have zero value as a person. Goodness: Dick Cheney is a heartless SOB but he loves his lesbian daughter. George W. Bush is a frat boy who’s lazed his way through life on his family money and his father’s power, but when he walks his dog he always cleans up the dogpoop. Margaret Thatcher drove the UK economy to destruction, blew away the oil money, broke the trade unions, but she was reliably pro-choice and supportive of pregnant MPs. I detest these people. But they don’t have zero value. I do not believe that anyone does.

      I don’t know what good you’ve done in your life, because I don’t know you. But I’m confident you’ve done things that give you value as a person, both in yourself and for other people. Even Batman occasionally manages that.

      Think to yourself: most really empathic people, most people you know who you think are wonderful people, most of them have at some time in their lives had the dark night of the soul when they think they’re worthless and no one should love them. I know this because it’s true of me, I found it’s true of other people I admire and respect, I think it’s true because I think goiing through that kind of emotional agony is how people learn about empathy.

      Instead of thinking about how you can get other people to love you, think about how they’re feeling. If you have something nice you can say about someone, say it to them. “That’s a nice haircut.” “You look good this morning.” “wow, you make good coffee.” Say thank you to waitstaff. When the supermarket checkout wishes you a nice day, tell them thanks and you hope they have a nice day too. It may be totally trivial, but no one ever minds hearing about the trivial good stuff. (Obviously, you do this in a non-creepy way. “Nice haircut!” is totally acceptable. “Nice ass!” not.)

      Practice random acts of kindness to total strangers because it’s *fun* to do things that will make some person’s life better and it will make you feel good about yourself.

      And making yourself feel good by having fun and making other people’s lives randomly nicer is a worthwhile goal. Donating money to charity is helpful, but feel free to do fun stuff like calling a local no-kill shelter, asking them what their estimated pet food bill for the week is (or the month, if you can afford it) then go in on their Open Day, tuck the cash they need into the donation tin when nobody’s looking, and then call their number on your cell phone to tell them it’s there. Stand around looking as surprised as Bruce Wayne while everyone is going “OMG HOW AMAZING!! WHAT SNEAKY PERSON DID THAT!”

      See? You can be superhero sneaky and lead a double life like Batman and not actually hurt anyone doing it.

      (I have a sneaky kind of envy about the Secret Apartment deal because actually, while sure it was cheaty and wrong and you should apologise to that woman for freaking her out, but still: the idea of leading a double life like that is sort of comic-booky fun. Freaky in real life relationships. Figure out which apartment you really want, and keep that one.)

    7. LW, I’m really glad you wrote back, because I feel so much more sympathy for you when you’re explaining your internal state than I did when I was having a knee-jerk reaction to your bad solution to it. Everybody else has been way more eloquent about learning to feel self-worth than I would manage on my phone keyboard.

      I’m really sorry to hear about the loss of your parents- it sounds from your comments that not growing up with the anchor of their love is a huge part of the reason why you feel so unmoored now.

      I think all the charity suggestions people have been making are really cool, and I want to add that you could think about doing something like Big Brothers/Big Sisters, which is a time commitment rather than a money commitment. You’d be able to make a really direct connection to a kid in need, which would have the additional advantage of giving you a relationship with somebody who’ll be less likely to notice your wealth markers and just be happy to have your time and attention.

      You might also be interested in the Brenee (?) Brown TED Talks about the power of vulnerability. I know those have popped up in the CA comment threads before.

    8. Oh, LW. I feel for you so bad. Partly because I was ostracized for years in elementary school, so I grew up feeling like I was essentially flawed, like no one would ever be friends with me because there was just something so awful about me that no one could ever love me. It’s so awful! Feeling unloved and ignored literally is the worst. Long-term, children who were badly abused grow up into healthier adults than ones who were never hit or shouted at–but neither touched or talked to. Neglect is actually worse for people than active unkindness. It’s why baby monkeys would rather be hungry cuddling up to a soft, warm “mother” than eat from one made out of wire.

      I am so fucking sorry you’ve had to live feeling unloved and worthless. You didn’t deserve it, and it’s hurt you bad. That is not a failing in you–it’s an ordinary and reasonable reaction to the experiences you’ve had. And it takes a lot to heal. I’m not minimizing how much crazy you’ve got going on, because god knows your circumstances call for it. But it sounds like you’ve got some things going for you.

      I honestly congratulate you on the work you’ve done so far. You’ve kept yourself together and got a great career; you’re helping other people; you managed a three-month relationship! And then you did the bravest thing: you risked vulnerability with the woman you cared about. And then when that went wrong, you asked CA for help.

      That does not say to me “someone who is going to be alone forever”. That says to me “someone who is willing to risk a lot to learn how to form relationships with other people.” That you’ve formed a caring relationship once means you have the capability and you can work on trying again.

      I really like the suggestion of volunteering with a children’s charity, especially if you can mentor or tutor. You obviously have an affinity for kids in tough spots, and you know deep in your bones how important it is for those kids to have someone who cares about them. That person can be you. If you work with a kid–face to face work, doing things that really matter, that is about you and not your money–it means both of you encounter the side of you that’s capable of caring for other people, that does that kid good just by saying, “You look sad, what’s wrong?” or “You did a really good job there, I’m proud of you.” Sure, you start out awkward at first, but a good organization can get you a little training on active listening and empathic responses to give you the essentials.

      Heck, do you have a pet? Something that loves like hell when you give it attention, affection, petting, or play. It honestly does help to have a living being out there that’s happy to see you, even if it’s not that bright.

      (Or stick around, Bruce, and see if there are other LWs you can give support, encouragement, or advice to)

      It may take years to feel as though you deserve to be a member of the human race, the same way it may take someone who was starved through childhood years to recover from the physical damage and rebuild healthy functioning. But the one thing that starvation has given you is hunger for human connection. You know how valuable it is, so you’re not going to ignore it as you grow. Trust and use that.

      Brene Brown’s stuff made me cry the first twenty times I watched/read it. I’m training to be a psychotherapist now, in a school that defines healthiness as “a sense that you belong, and deserve to belong, to a community that values you, that you want to and feel you can contribute to”. To me that’s such a huge, scary, ambitious definition, because it’s what my teachers believe every single person is capable and deserving of. But these days I believe it too.

  39. LW: I come from a humble background but have dated men with a significant wealth-gap… and there are pretty much two ways (in my experience) that rich men go about dating less wealthy women.
    a) completely flaunt their wealth. Take them to the Opera on a first date and buy them a dress. I literally had a man do this with me. I refused the dress, enjoyed the Opera, and didn’t accept a second date because I found his extravagant excess distasteful.

    b) just do what you like to do when you hang out with people. Go to a restaurant, go to a movie, hang out at the neighborhood dive, go for a walk. Things will unfold at a normal rate and eventually a smart woman will figure out “he must have money” or it will come up in conversation. But this can seriously take 5-10 dates if you’re just doing normal stuff.

    I have never had a man pull the full reveal secret apartment on me. I would have been mortified. I probably would have had a panic attack and would certainly have never spoken to him again. I honestly cannot think of a person who would respond to that in a positive way.

    You asked “How can I find people who like me for me while living a lifestyle that clearly shows how wealthy I am?”. And it’s true if on date one you pick them up in your Aston Martin that your date may be a little uncomfortable (or a little *too* comfortable). But who picks their date up any more? Meet at the restaurant. Don’t take her back to your apartment/have her meet you there until date 4-5. Be vague about details that may be more revealing than you are comfortable with (what part of town you live in, what you do for a living, etc). There is an important distinction between vague & lying, so you know, observe that.

    When it finally comes up naturally and you’re comfortable being a little more revealing you can say something along the lines of “I’ve worked hard at [ACCOMPLISHMENT], and been rewarded handsomely. I like having an apartment with the view of the city and I feel really lucky that I can afford it.” then change the subject and move on.

  40. I think it’s adorable that everyone is saying, “Don’t be like Batman!” and then calling you Bruce, LW. 🙂

    I just want to second the get-a-pet and work-with-kids advice. I have done both, and am glad I did!

    And about working with kids – I taught music in an elementary school part-time for 4 years, and I just want to say that starting to work with kids can be really terrifying. I didn’t have any kid experience, I didn’t know how to talk to them or relate to them or what they would understand or anything. But I just dived in and it was fine. So on the off-chance that you (or someone else reading this) has thought about volunteering with kids, but been scared to do so, I just want to encourage you to dive into it. People will say, “Kids love you for who you are” but that wasn’t my experience – mine was that “Kids will love you for being there.” If you show up, and treat them with respect, they will give you a lot of affection and that can be really great. And they are really not like adults at all – they have their own little alien culture – so they can be a great break from adults if you need that.

    1. This, so much. So many kids don’t get treated with respect. Even mostly happy kids from loving families aren’t necessarily treated with respect, because our culture says it’s ok to treat kids very differently from adults. And in some respects that’s appropriate, but I think we go too far with it. An adult who never talks down to you, who takes you seriously, who doesn’t just tell you “It will pass” or “You’ll grow out of it” when you have a problem (even when it’s true) — every kid should have someone like that, and so few do. It sounds to me like you’d be really good at that.

      Nthing the “get a pet” part, too. They’re good company. They love you. They provide that physical contact that is so important — people can need widely varying amounts of touch to feel happy, but almost everyone needs some. (If you’re allergic to the furry kinds, reptiles can be surprisingly good companions. Goldfish, not so much.)

  41. Okay, so I’ve been sleeping on this one. And I’ve finally come up with the solution. How to get a girl to fall for you and not your wealth, without lying, and while having a good time!

    Step 1. Meet a lady that you like that likes you. Good luck. This step is always the hardest.

    Step 2. Ask the lovely lady out on dates. No fake apartments (if you still feel the need to pay rent on another, you can pay the rent on mine.) Take her to fun and exciting places that don’t scream wealth but don’t scream poor either. Do dates that you can both wear jeans to (amusement park, zoo, flower conservatory, etc) and have a good time at. Do not go back to your place after. Go to hers, or part at the last place you’re at (or maybe drop her off. You can show her you have a nice car. Avoid other financial discussions, just say you’re not comfortable talking about it yet. Do talk about growing up, what school was like, etc, even if it means admitting into having well off parents growing up.) OR, take a taxi.

    Food dates. Okay, these get a little trickier. Do some cheap places. Don’t worry about being out of class, some of them are worth it. (For real. Best asian food in my city can be found at these two restaurants, each with a meal like no more than $7.00, served in styrofoam, and plastic when they’re feeling classy. The dining area in one is really nice. The other is dim lit, booth seats sometimes ripped, BUT BEST LO MEIN EVER.)

    Go for ice cream in the summer, or italian ice, or frozen yogurt. You can do indoor dining, or sit outside on a bench.

    This covers casual. Now, for classy. Tell her you want to treat her to a special night, and tell her to dress up. Pick her up. Take her to classier places and things you’d prefer to include in your lifestyle and dating. Remember, tell her it’s a surprise, special night that you want to treat her too, that ways she’s not feeling pressured to be able to pay for it.

    Do a healthy mixture of cheap, fun, and classy dates. I think you’ll find a lot of the “cheap” dates can be just as fun as classy.

    Step 3. After things have been going well for a while, mention you’re doing pretty well in life. She’s gonna have some idea of this already. Do feel free to mention you’ve been insecure about it, but don’t want to lie about it, or super hide it, but don’t want to flaunt it either. Give her a week* to get used to this. (*this time frame may be varied by her reaction. If she’s very overwhelmed, give her longer. If she’s not overwhelmed and excited to see your place, feel free to shorten.) Then let her see your apartment.
    Important note: Make sure she knows you have fun with her and generally like/love her. Don’t let her feel like you’ve been making fun of her place or dating the cute little poor girl or anything. She needs to know you genuinely like her and enjoy dates both classy and at places like the zoo or whatever- both for her company and that you enjoy doing things that the rest of the “real” world does. Really make sure she knows you enjoy her company, being with her, and the like.

    Step 4. Meet the parents. She needs to meet yours. You need to meet hers. Have fun, this step doesn’t get easier or harder with tips and tricks.

    Step 5. Engagement and all that other jazz. Assuming things go well enough, you’re going to make it to this step. Go with your gut on what to do here, be it engaged at the top of a ferris wheel or a fancy restaurant or your favorite noodle place. This is much farther into your future though, worry about it then.

    Step 6. Wedding. This is up to her. Let her plan how fancy or non-fancy she wants. Feel free to give advice, because this is *your combined wedding,* but remember, this is what she’s dreamed of from childhood, and you don’t want to overpressure her and her family, and she’s gonna know that your family may be judging.

    So yeah, there’s my advice from sleeping on it. Potentially, not nearly as good as a lot of the other advice here, but I figured there are some timeless dating things that don’t require wealth to do and let you get to know each other before stepping things up a little. That ways you connect for the important stuff. Or, feel free to totally scrap this if it seems to have no value to you whatsoever.

    Everyone else, feel free to critique or give supplemental suggestions or whatnot. Hopefully we can be helpful. ^^

  42. Late as always, but just in case people are still reading: I think I read the ‘secret apartment’ thing a bit more charitably than some of the other folks in this thread. Rich people often have more than one place. When I first learned this, I was completely mystified: who needs more than one place? How does that even work? But it does happen, rather a lot actually among the 1% it turns out — “my house, my cabin, my chateau in the Pyrenees, and the overnight apartment I stay at when I’m working late downtown.” I wonder if LW simply had a big place and a little place all along, and decided to take his date to the smallest one. It’s still a misdirection and a bit weird and a weaksauce way to deal with wealth anxiety… but when I read the letter it didn’t strike me as “OH MY GOD HE CREATED AN ENTIRE FALSE REALITY, MATRIX-LIKE, JUST TO TRICK A LADY”. Of course I could be wrong, and if the dominant reading in the thread is the correct one and he did create a Matrix, then I totally vote for “ew, creepy, stop that”.

    I, too, have been on both sides of the wealth divide — in fact I’m sort of both sides at the same time right now, with different groups of friends — and it can be really uncomfortable in a way that can’t just be dismissed with “if you’re feeling awkward about going to such-and-such a restaurant then it’s totally your problem and you should get over it.” I happen to be dealing with this IRL right now with a group of friends who are much wealthier than I am, and who end up having conversations I simply can’t contribute to because they involve a lot of things I can’t do: world trips, four-digit impulse buys, constant tech upgrades, and so on. They are not flaunting their wealth or being assholes; they’re just talking about their lives. But the very nature of those lives can feel exclusionary and it’s hard to deal with my discomfort about that sometimes. It’s on me, I totally get that and I’m working on it, but it’s not fair to characterize the problem as JUST my insecurity.

    Similarly, my own level of financial comfort can be alienating to people less wealthy than I am. I get a latte a couple of times a week on my way to work, and I know people (including myself, 10 years ago) who would consider that $5 coffee a major treat, something you need to plan for for days and recover from later. A casual mention of my daily latte might be as alienating to some people as my friend’s new iPhone is to me. Yes, a person’s money anxiety is theirs alone to deal with and I shouldn’t have to censor myself and it’s my right to enjoy my latte and I am genuinely happy for my friends who can buy exactly the phones they want three times a year etc. etc. etc. etc. The good Captain is exactly right about all of that, and I hope the LW heeds her. That said, it is good to realize that all the conversations we have create little universes inside them, and for people who are not naturalized citizens of those universes, it can be a strain on a relationship. I congratulate the LW for recognizing that and wish him well in creating a universe that can include all the new friends he likes.

  43. This is all wildly fascinating to read. I grew up poor, I’m still poor and I’ve never dated anyone who wasn’t as poor as me.

    I would also be upset if someone lied to me about their wealth. Mostly because I find myself thinking it would get in the way of me successfully avoiding wealthy people. I cannot get past the mind barrier that would consistently remind me that said wealthy person is always going to think I’m lesser.

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