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.