Archive

the art of no

We are overdue for the blog feature where I answer the search strings people typed in to find this place as if they are questions. Let’s do it!

First, as is traditional, a song:

 

RIP to one of the coolest, realest artists I was lucky enough to share the space-time continuum with.

:cries for the 100th time this week and it’s only Tuesday:

:cracks knuckles:

Let’s do this.

1 “How to tell someone you don’t like talking on the phone.”

I’m not a phone person – can we take this to [text][email][chat] instead?”

“I can’t do a phone call right now, can you text/email/message instead?”

It’s okay to have strong preferences and needs around how you best communicate, and it’s also okay if those preferences are flexible and negotiable depending on who you’re communicating with, your mood and energy levels at any given time, what people in your life has access to, their strong needs or preferences, etc. You absolutely don’t have to have one blanket rule for everyone in your life or strive to be fair about this.

I wasn’t the biggest phone person before, but it turns out I prefer it vastly to Zoom (there’s a reason for that), and I’m enjoying catching up with people like it’s 1991 again, flat on my back with my feet up, twirling the charging cable around my finger like it’s an old spiral phone cord.

2 “Is it normal to hate talking on the phone when dating?”

It’s normal – or at least not uncommon – to not enjoy the phone or prefer different means of communication (see above).

I think the necessary follow-up question here is: Is it the medium or is it the conversation partner? If you don’t usually like talking on the phone, but your companion makes a normally difficult thing fun and easy, that’s a good information. If you don’t usually like talking on the phone and this person makes the prospect even less appealing, or if you do like talking on the phone with friends and family but not with this person, that’s interesting information about chemistry, compatibility, communication styles, etc.

Social distancing means that in-person dates are on hold for now and people can’t rely on non-verbal chemistry so much so figuring out how and whether you can have a comfortable, connected, enjoyable conversation with somebody is front and center for the time being. I think it’s always good to pay attention to your own enjoyment and comfort levels, especially when first getting to know someone, and “am I actually enjoying this” is perhaps a better question than “am I weird for not enjoying this as much as I think I am supposed to.”

3 “It it appropriate to put a sign on door to let neighbors know you’re resting.”

I love looking at a posted sign – especially a highly-specific rule – and wondering “What’s the story that prompted this?”

This question is a bit like that. There would be no need for a sign if these specific neighbors weren’t prone to interrupting during rest periods, right?

In that case, a sign that’s like “I work nights, please do not disturb” or “Don’t wake the baby” and then redirecting anyone who would be tempted to knock or ring a bell to another means of communication (email, text, leave a note on one of those dry erase boards people hung on their doors in the dorms) might work. “Leave your calling card on the silver tray in the hall, Jeeves will see to it.” 

Sometimes people see general “To Whom It May Concern” notes and think, “Ah, but they don’t mean me,”  so consider having a conversation with said neighbors along the lines of “Please text or email vs. just stopping by and I’ll get back to you when I can, or leave whatever it is on the mat, I’m often resting during the day and would prefer not to be awakened unless it’s a true emergency.” 

4 “My husband teases me always about my health problems.”

NOT COOL.

If you’ve already had one sincere “Stop it, that’s off limits for jokes” conversation and he’s still doing it, your husband could be afflicted with Irredeemable Asshole Problems.

Post-quarantine I’m envisioning a National No-Fault Divorce Day, with flower crowns and maypole dancing like in Midsommar as everyone celebrates being freeeeeeeeeeeeee. There will be pro-bono lawyers working the crowd, and judges at kiosks throughout the park, and in the parking lot a giant swap meet for household items as everyone tries to rebuild a functional kitchen from their half of what’s left behind. “I’ve got two blenders and a bread machine I never use, trade you for a cordless drill and a decent cutting board?” “No cutting board but there are three jars of coriander in my spice cabinet, I can throw in the drill, some placemats, and a home brewing kit?” “Done!”

Maybe see you there?

5 “Grown men who only want to smoke weed and play video games.”

If you meet an adult man who likes doing this *and only this* with his free time, probably assume that this is pretty much how he is. Weed is relaxing and video games are fun and there’s no upper age limit where that’s not true of the people who find that to be true. Assume that he has chosen freely and leave him to it!

If this is not how you are (just guessing from the “grown men” phrasing), look for partners, friends, housemates, co-parents (!!!), etc. who do things that you enjoy (or at least don’t find stinky, ridiculous, and annoying).

How a person actually is at their current age > How you think a person should be by a certain age, so select for current compatibility, not imagined future potential. You will be so much happier if your relationships aren’t ones where you see yourself as the responsible, permanently irritated parent sniffing everyone’s hair to see if it smells of concerts and view the other people in your life as permanent Large Adult Sons with bloodshot eyes who need to be motivated and molded into something else.

6 “My parents text me too much.”

If you’ve tried asking them to cut this down and it hasn’t worked, or if the pandemic is bringing out old anxieties and old habits that you thought were settled, try responding pleasantly at regular, predictable intervals when you have the energy and capacity to reply, and completely ignoring non-emergency communications from them the rest of the time. They may not like it (and may temporarily increase the flurry or test your resolve) but they will very likely adapt to it if you stay consistent.

You might slightly reduce conflict even further by changing any conversations about this from “You text me too much! Jeez!” to being more about you and your own self-care habits.  “Oh, I’ve been putting my phone on silent so I can read in the afternoons.” “I’m trying to not be glued to the news and social media, so I’m logging out for big chunks of time every day,” “A good window to reach me is between 5:30 and 6:30 pm, if I don’t respond right away I’ll try to check in around that time every day.”

My folks are not frequent texters but this seems like a good time for the story of how I was in class & meetings all day with my phone off and then went to the movies without checking messages since I just needed quiet, and the dark, and solitude, and Thor: Ragnarok on the biggest loudest screen I could find.

I came out of the movies, went to a solo dinner, and finally turned my phone back on to find a bunch of texts and voice mails from my mom along the lines of “Please call when you get this.” “Still trying to reach you, get in touch when you can.” It’s like, 8:30ish my time so 9:30 pm on the East Coast, everybody should still be up, so I call my mom’s cell back. No answer. I call my dad’s cell. No answer. I call the house line. No answer. I leave voice and text messages everywhere, and start to worry. There is zero chance that they are not home at 9:30 on a random Tuesday unless something’s up, so what’s up?

I call my older brother’s cell – is there an emergency? – no answer from him. Now I’m really worried.

Does my aunt know what’s up? She at least texts back that she knows of no emergencies but she’ll check.

When I finally hear from Mom, she tells me she called and texted because she has a question for me. Oh? Ask away! I’m dying to know!

The question? She wants to maybe buy a machine to convert Dad’s extensive VHS collection* to DVD or computer files as a holiday present and did I know which one was good? Otherwise maybe we’d have to find him a new VHS player on eBay because his most recent one gave up the ghost and he had nowhere to watch his stories. And sorry about not picking up phones, they’d both fallen asleep on the couch watching TV as had my brother.

When my heart rate returned to normal, we made a family agreement that thenceforth A LITTLE CONTEXT with any “please call me” texts or messages was ABSOLUTELY MANDATORY.

*Lest you thought I was the most intense cineaste in my family, my dad’s deep attachment to his VHS collection tells a different story. ❤

7 “My husband is not re-evaluating his life at all since the corona but I feel that I must leave because he has shown me that he has no empathy at all.”

There are going to be a lot of divorces in the next two years and that’s probably a good thing and I promise am not making light of how painful that is with all my party planning earlier in the post. (“Two, no make that three, working can openers…who’s got a bread knife?”) 

People get married for lots of reasons, one of those reasons is “You are the person I’d most like on my team when the rough parts of adulting come for us” (sometimes summed up in vows as ‘…or for worse’ ‘In sickness and…’ and ‘…and for poorer’). A partner who knowingly and uncaringly makes a crisis harder on you? Somebody who shows you that they are not on your team? Isn’t the right match for what comes next, even with the best of hopes and intentions. I’m so sorry, I hope whoever searched for this is staying safe and being very kind to yourself and making solid plans for a safe landing.

8 “My partner wants to go everywhere with me is that healthy.”

Pandemic life is making it so nobody is getting a balanced, preferred, comfortable, safe, ideal mix of alone time and togetherness, but in general,  if you’re dating someone who wants a different amount of togetherness than you, it’s 100% an issue of compatibility and 100% worth discussing, like, “You seem to want to do everything together, but I need a certain amount of alone time and one-on-one time with my other friends and family to be happy. Can we agree that I’ll be more proactive about inviting you along when I want to do stuff together, but if I just say ‘I’m going for a bike ride,’ it’s neither an automatic invitation nor is it a rejection?” vs. “Hey, I have a lot of anxiety about being invited, included, excluded, and not reading the room about that stuff so can you make it really really clear when you are inviting me and is it okay if I ask what you mean? I promise I’m not trying to pressure you if the answer is no, I just can’t always tell, and everybody who has ever told me they ‘need space’ broke up with me within a week so it would reassure me a lot if you could be way more specific than that.”  

Maybe from there you can figure something that works for everyone, but “Nope, together, always, or else you don’t love me right!” definitely isn’t the default setting.

Insisting on constant contact and togetherness with a partner (which often goes hand in hand with excessive monitoring of their activities) is a means of control. If this applies to you, I recommend looking at the resources the good people at LoveIsRespect.org have put together as a way to start planning a safe way out of a relationship where this is the norm. 

In either case, “Healthy,” “normal,” etc. aren’t reliable markers of what you’re allowed to need and expect. If someone convinced you it was perfectly normal and healthy to want to do literally everything with you, and this is how all other couples everywhere interact, like “We’re in love now, Google it” and you didn’t want that? Then you’re the boss of you and your needs are important whether or not they match a template. ❤

9 “How to respond to a guy on online dating who asks ‘what are you looking for on here?'” 

I’ve answered versions of this many times before, whether sincerely (Be very honest about what you are looking for, including “I don’t actually know” or “I’m hoping I hit it off with someone who will want to get married and have kids someday” and “I am looking for a bag-pipe playing sex unicorn with large feet and a larger trust fund” if those are what’s true for you) and jokingly (“I’ll know it when I see it.” “A willing patsy for a Double Indemnity-type situation.” “Hmmm, you seem like you have an answer prepared, so what are you looking for?”)

Can we be very, very honest today?

I haven’t online dated since 2012 but I did a ton of it before then and I’ve done a lot vicariously through my friends and all of you in Awkwardland.

“So…what are you looking for on here” is a very basic question, an obvious question, and it should be a fairly neutral, easy question with an obvious answer (“I’m looking to…date…people?”). I shouldn’t be mad at it. People are testing the waters, it’s understandable, it’s like “so…what do you do?” in the pantheon of American small-talk. The oatmeal of questions. Not everything has to sparkle, goddamnit.

And yet, I’m pretty sure I’ve never once had an actually good date where I wanted a second one with anyone who has ever asked me that. Just seeing it in my search terms month after month makes me want to yell SWIPE LEFT at it.

Theories as to why it bugs me so much:

  • I didn’t use online dating to meet women (browsing in feminist bookstores while sporting a strong shoe-and-glasses game worked for that), so my online dating experience is 99% with straight cisgender men and this immediately reads to me as a question that a guy asks every single person they write to right off the bat whether or not he’s read your profile. The dude who was just playing a numbers game of sending the same message to everyone to see who bites? That dude had nothing for me, nor I for him.
  • It’s not a connecting sort of question, it’s a weed-out sort of question that makes a flirtation suddenly and immediately feel like a job interview.
  • I feel like there’s always a secret question in that question, and it’s never a cool secret question, it’s more like:
    • “I can’t think of anything else to ask and I have no idea what I’m doing.” Honestly, fine, this is the most benign, salvageable version of this, let’s just get through this in one piece.
    • “Let me zero in quickly on whether you are looking for the same stuff I am, but in a way that makes you put it out there first.”
    • “Let me zero in quickly on what you’re looking for so I can pretend that’s what I want, too, just long enough to possibly have sex with you with the minimum effort on my part.”
    • “Let me zero in quickly on what you’re looking for in a way that makes you try to guess what I’m looking for and tailor/audition your wishes to what you think I want.”
    • “I get more casual sex when I pretend that I’m looking for a relationship and less when that becomes apparent so I like to keep my wants ambiguous until I know what I’m dealing with.”
    • “If I know what you are looking for, I can selectively edit my life correctly to seem like I fit the bill long enough to entice you to overlook the sketchy stuff like how ‘separated’ means ‘I absolutely intend to tell my wife someday that I want to separate, once I’ve met the right new woman’ and ‘single’ means ‘separated.'”
    • “Let’s not waste time with small talk, a total stranger I just walked up to in a virtual bar. Are you going to try to trick me into making babies with you right away or are you going to be cool and let me date you for 8 years while I wonder if parenting is really right for me and then leave you when it’s too late for you to make babies because I got my 23-year-old assistant pregnant on last quarter’s sales retreat and now I think it’s time to really follow my dream of being a dad?”
    • “You’re not going to try to gold-dig my $27,3000/year salary like all those other lying vultures who couldn’t appreciate a REAL MAN who is NICE, right?”

It’s an obvious question so the answer should be obvious, too, right? So why is it a constantly recurring question in my inbox and my search data?

I think at least some of the anxiety about answering it is about sensing there some kind of a test being administered by someone who is already showing they haven’t put much thought into things. Like, there is clearly a right answer, something they are looking for, so why won’t they just say? Or, it gets asked so often, like one of those job interview questions like ‘what is your greatest weakness’ so surely someone has written a guide to turning it around, like ‘my greatest weakness is actually how awesome I am,’ so can someone put out the cheat codes already?

“It’s just efficient for figuring out if you’re on the same page or not.” You know what’s efficient? Actually reading people’s profiles and only messaging the ones who seem like they might like you and vice versa. See also: Leading with what you are looking for.

If you have asked this question in the process of dating, or love someone who did, I don’t think you are inherently boring or bad. “Do we want the same stuff y/n” is an important question for finding someone who is compatible with you, so please do not feel the need to share examples of how this is good, actually, I blanket-believe you and blanket-support you in your happy love story and I will die content in my theory that it worked out because you quickly skipped past this awkward question the way people fast forward past “so what do you do” and found something meatier to talk about when the formalities were over.

But my answer to the general “how should I answer this?” is, now and forever:

Answer it literally however the fuck you feel like answering it at the time. Do not worry about giving a “right” answer, secret or otherwise, because there isn’t one. There’s only what you actually want and how it intersects with what the other person wants.

However you answer, it will either lead to a fun conversation where you learn something true about each other (because everybody starts asking & answering more specific questions), or it won’t and you’ll probably never have to talk to the person again.

If you fail a total stranger’s boring secret test? OH WELL, GUESS YOU WANTED DIFFERENT THINGS FROM LIFE.

Please never, ever worry that you will get this wrong somehow or that there was some magical, maximally palatable way with just the right mix of reassuring and fascinating and sexy but unthreatening way – like the hot girl taking off her glasses at the end of a 1990s movie about prom dates and becoming the Objectively! Hot! Girl! for a moment and then putting them back on and becoming accessibly hot once more-  that  you could have answered  that would guarantee that the person would have fallen in love with you if only you had known what it was.

Thank you for coming to my Ted talk.

10 “What to say when someone says ‘why should I date you.'” & “What does ‘Give me one good reason I should date you’ mean in online dating.”

I had just typed the answer to #10 and then dipped back into the search terms to see if there was anything else, and found…this. Okayyyyyyyyy.

Why should I date you?” 

SWIPE LEFT

Why should I date you?” 

Sounds like a you-question.

Why should I date you?” 

Sir/Ma’am, this is a Wendy’s.

Why should I date you?” 

SWIPE FASTER. LEFT! ONLY LEFT!

“Give me one good reason I should date you.”

You…messaged…me? I don’t actually know who you are? Wat?

“What’s one good reason I should date you.”

Lol, I’m not going to date you, but I’ve got five minutes, so be honest – does that actually ever work? Do people actually start listing reasons like they’re trying to convince you that you should take a chance on them? Tell me all about that!

Look, there’s an outside chance that “what are you looking for in a relationship/ on this site” is a sincere question with no hidden messages or tests, we all start somewhere, basic is always better than mean.

“Why do I actually want to date this person” is a question to ask oneself, definitely explore that.

“Why should I date you?” is what you ask when you think Alec Baldwin is the hero of Glengarry Glen Ross and you practice the speech in the mirror to yourself in the morning when you think no one is looking but hope that at least one of your housemates is awake enough to overhear how hard you nailed it today and you jerk off in the shower to the tantalizing prospect of a worshipful secret audience while your housemate desperately googles “Best earplugs for total silence.”

“Why should I date you” is for when you are actually contemplating becoming a contestant on The Bachelor and you know that the dullard-of-the-month-club is 100% going to ask you that on camera and you need to find the right mix of charm and smarm to snag your rose and the opportunity to go on a humiliating hot air balloon ride “solo date” while America watches you resist your impulse to toss this polo-shirted absolute void out of the basket like excess ballast and rise, rise, rise forever into the sky, victorious and alone like some avenging Valkyrie, in which case, carry on.

“Why should I date you” is a “neg”, in my opinion, which is a gross, pathetic pick-up-artist strategy designed to manipulate you into auditioning for being worthy of someone who would ask you THAT instead of wondering wait, why the hell am I auditioning for this person’s approval? Can’t they see I’m hot and cool and nice? Is this actually a job interview? I don’t actually want to be on The Bachelor?

Friends don’t let friends reward negging. Never answer this question. It’s a trap.

Comments are open. Be gentle. Be gentle specifically with me, I’m rusty. ❤

Hi Capt. Awkward,

I/she/her am a high school teacher and we’re not returning to campus until next year. That means we have 12 more weeks of distance learning. Right now we’re completing Week 3.

I have a student (11th grade, so around 17) who has a variety of mental health needs, gender identity stuff, etc. This student and I got along very well when we met on campus, and I was able to make a good and empathic connection. The kid likes and trusts me. I knew before we went into the shelter-in-place that the kid’s parents aren’t very keen about the gender identity issues that this kid has.

Fast-forward to now. All of my students are sheltering in place and all of us teachers are trying to figure out distance learning. I figured very early on that we wouldn’t be coming back to campus for at least 2 months, so as soon as we were sent home I started a Slack workspace and invited my students into it. We keep in touch on a daily basis and I help them and, overall, Slack’s been great.

Except this student of mine, who I am very fond of, is stuck at home with their unfortunate parental situation. Like most of my students, being at home with the parents 24/7 is wearing on them. Add to that the gender stuff and the mental health issues, and the student really needs someone to talk to. They’re in pre-crisis mode. So the student has been reaching out to me.

I spent several hours last Thursday evening chatting with this student in Slack, and they told me several things in strict confidence (nothing alarming or that would require CPS reporting, but very personal, like what you would say to a friend). I was really trying to be there for the kid, but I ended up with searing pain in my legs from sitting for so long in my office chair – this was after a solid day of sitting at my computer, working. I was there for the student, but I also suggested the student find their own people, their peer group, folks with the same gender identity experiences, mental health needs, and so forth.

I’m worried that the student currently sees me as the only person who is sympathetic and approachable, and that the student will then want to talk to me for several hours at a go, several days a week. I am sympathetic to the student, but the student isn’t my friend, and I have my own family concerns and mental and physical health issues. I don’t want to leave the student in the lurch. I want to be supportive. I want to do a good job as a teacher. And I recognize that these are strange times and that nothing is going the way anyone expected and I should have added empathy and availability for my students, but I’m already stretched pretty thin here as it is.

How do I tell the student that, while I’m there and interested, I can’t do these 4 hour long conversations while my legs are screaming in pain without hurting their feelings, making them feel rejected, etc.? How can I further reinforce that they need to find their own Team You without sounding dismissive?

–Just a teacher

Hi there, Just A Teacher,

You did a very, very kind thing for your student that day.

Can you try to sit with just that for a moment?

Let go for a moment of framing this in terms of boundaries, professional conduct, the future, the fear of  letting someone down in the future, or the panic of being stretched too thin and wanting to conserve your resources for yourself and your family. You’re skipping ahead to anxiety and guilt about “what if I can’t do this next time/all the time” before letting yourself feel good about what you did do, i.e. When the chips were down and a struggling student needed you, you were there.

You might not always be able to be there in exactly that way, nobody should expect you to do that all the time, it’s okay to set limits and offer alternative support systems, you can’t singlehandedly stand in for a school full of peers and counselors and fellow teachers or make up for the lack caused by faulty parenting, that’s all true! But none of that changes the importance of what you did that day. Can you let that generosity and service and grace be the starting point of the story, just for today, instead of coming at it from a place of scarcity?

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Dear Captain Awkward:

Well, not exactly. First, some background: I (she/her) am a member of a Face Book group for fan-fiction readers and writers. I’m a longtime writer of both original work and fan works, so I like to leave comments when people post questions about plotting, characterization, etc. Trouble is, I commented on one post a couple of weeks ago, and now the original poster won’t leave me alone.

It wasn’t so bad at first. She private messaged me within about an hour of me leaving the comment, specifically requesting elaboration on what I’d said. Sure, fine, not the first time this has happened. We kept chatting, about the fandoms we were in, that sort of thing. Hey, great, maybe I’m making a writer friend, I’ve been looking for that. And then she dug a little deeper into what I liked- did I read/write mostly G rated or X rated, was it mainstream stuff or fringe, etc. For the sake of the story, we’ll say that I ended up saying, well, I mostly like m/m, I sometimes like f/f, and I’ll only read m/f if it’s really special, and that I really like reading when men tie other men up and have sex with them. So she starts sending me bits and snippets of stories she’s been writing, and most of them turn out to be m/f, where the woman is being tied up to work through childhood trauma. And in between there are questions- “if her legs were tied like that, would she be able to stay in that position?” “would he check in with her at this point, or would he just keep tying knots?” I’ve tried to answer and respond in good faith, but it’s becoming draining. Worse, as all this has progressed, I’ve realized that the writer herself probably has childhood trauma surrounding being tied up, and she is using the writing, and by extension me, as free therapy.

I didn’t sign up for any of this! I was never even asked if I was up for (or even interested in) so much as being a beta reader, let alone this mish-mash of editor and therapist that I’ve been shoehorned into. I’m generally a big fan of “use your words” but this situation has me speechless. Can you recommend any scripts to disentangle from this boundary-challenged person before I say something I’ll regret?

Thanks for all you do!

Dragooned

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Hey Captain Awkward.

I read some of your responses to other writers who had concerns about their partners’ finances, and I feel like this is related but not quite the same.

I’m stressed about my boyfriend’s money management skills and how I can help him without getting myself into a bad financial situation. I also recognize that he’s probably embarrassed on top of being stressed, so I’m trying not to make him feel ashamed. He was raised below the poverty line and when he made it “big” in his industry, he was earning huge salaries, so I think he’s allowed himself to fully enjoy it. Now he’s unemployed but is still living a “huge salary” lifestyle.

About me: I’ve always lived pretty frugally. I’m kind of a prepper in some ways – I buy a lot of dried or bulk foods, and I park nearly a mile away from work and walk every day so I don’t have to buy a $400 annual parking pass, plus I get some exercise which is hard to come by in my 9-5 cubicle lifestyle. My mortgage is manageable, 90% of my furniture is thrifted (thank god eclectic/Boho decor is “in” right now), I pay my bills on time, I have a modest emergency savings, and I have excellent credit — with a little bit of revolving credit card debt. My house is my first home purchase, and in addition to receiving some assistance from my grandparents, I participated in a federally funded first-time home buyer program and saved for years to come up with the down payment. My house isn’t fancy, but I love it because it’s mine goddamnit, and after changing addresses every year for 18 years, I finally get to lay down some roots! I‘ll hit my one-year anniversary of homeownership next week. Yay.

I do not typically seek out partners with tons of money. In fact, I’ve been known to date transient wildlife biologist types who briefly stay in the area to work for six months out of the year, and then squirrel their earnings away to get by the other six months. I just happened to fall in love with my BF who – up until last summer – was successful in his career, made a lot of money as a senior level designer with some recognizable household brands, and was promptly relieved of his duties the same week we met. He felt it was a blessing in disguise because he’s burned out on doing design for a living and wants to pursue his passion of selling rare European cars.

BF was earning a gratuitous salary last year, and while he lived within his means, said means were extravagant and now unsustainable: he owns two houses and has 7 cars (or 8? I actually don’t know anymore). Again, cars are his hobby/passion, as well as his side business, so some of this is to be expected. Two of them are “investment” items that will continue to appreciate in value, two are for driving, and the rest are “projects” that he plans to sell… but as you might imagine, this ties up a lot of capital in non-liquid assets.

BF is hemorrhaging money, but not cash, and is putting a lot of charges onto credit cards. He justifies this by saying that most entrepreneurs fund their businesses through credit. BF also owes his best friend a sizable amount for a recent generous loan which seems to have strained their friendship a little.

Three months ago, BF put his second house, which is in a popular resort town a few hours away from where we both live, on the market. He’s received multiple offers on the second house, but due to complications beyond his control, they continue to fall through, and so it remains on the market. BF was relying on the sale of this second house to kick-start the car business.

His monthly expenses (e.g. mortgages, private school tuition for his two kids, and commercial space for his new business) are over $5k. Not included are utilities, groceries, gasoline, health insurance, pet expenses, or anything else fun/recreational like an occasional meal out or outing to the nearby large city. BF has very little income right now except for infrequent freelance design work which he loathes and the car side hustle. Currently, he sells a car every 4-8 weeks and each sale results in a few thousand dollars. I in believe he’s receiving unemployment, but I’m not sure that he’ll qualify for much longer.

I told him he could sell his primary house and move into mine if he wanted. My mortgage is literally half the size of his, and if he paid HALF of my mortgage he’d still save $2k/month. However, he doesn’t want to sell his primary residence for a lot of (legitimate) reasons, and he wants to keep trying to sell the vacation home that’s been on the market for four months. OK, I get that… But right now, it’s just him and his dog occupying a 3,000 square foot space. He wants me to rent out rooms in my house and move in with him (I would contribute to his mortgage, which would only cover 25% of his monthly payment). I am considering it, but I’m also so happy to finally have a home of my own… it would make me sad to move out of my first home so soon.

I know he’s filed for bankruptcy once before, and he recently said he doesn’t want to do that again (he said it semi-jokingly, so I don’t know how much of a real possibility it is for him). He also told me early on that he thought I’d be a good influence on him as far as spending habits go. These were yellow-orange flags for me at the time. Now, he’s asking me to go with him to a cousin’s wedding on the absolute opposite side of the country in two months. We both have airline miles that will cover the trip, but it’s honestly not how I want to use those miles — the whole reason I got a credit card that gives airline miles is because he suggested I get one so we can travel overseas together this year. I wouldn’t have taken out a second line of credit if I didn’t think we weren’t going to use it for an *international* vacation. Plus, the wedding trip in two months becomes more expensive when you add up the other items that will not be covered: lodging, dining out for five days, hiring a pet sitter for our two dogs, rental car, etc. And I’m also just feeling less and less secure about out future together as the weeks roll by. Like what kind of message would I send to his family by attending this big family event if I’m not sure how into/secure I feel about the relationship by the time the wedding rolls around?

He has also half-joked about how I should have offered to pay for a recent ticket he got because he’s so broke. (He wouldn’t have received the ticket in the first place had he agreed for us to take my car that morning — which gets twice the MPGs — instead of his… but he insisted on taking his car. It apparently didn’t have a front license plate which resulted in a ticket.) The irony is that I almost offered to pay for it as a “sorry you’re broke, happy belated birthday” gift… but after he said that, I thought “NOPE. Nevermind; I don’t owe you shit.”

Let me preface that BF is the closest I’ve found to “my person”, if you get me — our connection, chemistry, and compatibility are mind bending. I’ve dated a lot of people in my day and never felt about them the way I do about him. I want to live with him at some point, get married, and maybe even have a child. How can I communicate my concerns to him without compounding his stress and sounding like a tightwad? (Also… Am I a tightwad? I’m starting to doubt myself and my saving habits…) And how do I support him without getting myself into a bad financial situation of my own? I don’t want to lose my savings, wreck my good credit, or be his cash cow, but I do want to be there for him in a way that empowers, not enables. I can see a future with him… so do I just sit tight through this rough spot and hope it all works out soon, or am I aboard a sinking ship and just don’t have the perspective to see it? Also, is there a way I can get out of attending this wedding?!

Thanks Captain Awkward!

Hello! I am so glad you wrote!

And congratulations on this month’s award for “burying the lede”! I retained the subject line of your email as the subject line of the post because I wanted readers to ride the same “oh, only 7 cars? Or is it 8?” roller coaster I did. 🙂

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Image: A certificate for excellence in “buring the lede in an advice column letter”

You have been so candid and such a good advocate for yourself that it makes my job very easy. My advice is:

  • Do not jeopardize anything about your finances or housing to “help” or “support” a man with 2 houses and 7-8 cars. 
  • Re-examine the idea that it is your job to help him figure out his money & his relationship with money. 

I’ll elaborate but here are some scripts:

  • “I do not want to move out of my house.”
  • “I do not want to move out of my house to make housing payments on a house I don’t own.”
  • “I’d rather save my miles and money for a vacation than go to that wedding, and I can’t afford to do both, so you’ll have to fly solo on that one. I’ll have to meet your family some other time.” 
  • “We approach money really differently, and I do not think it will be good for either my credit score or our relationship if we combine money or housing, especially while you’re still getting your business off the ground.” 
  • “I want to help you through this, but ultimately it’s your money and your decision, so one way I can ‘help’ is by having really clear boundaries especially around financial decisions that affect me.” 

Additionally, scriptwise, be very blunt and specific about money in your dating life. Do not let this flounder in expectations and hints, get in the habit of nailing stuff down like where are we going, what is the anticipated cost, who is paying. When you are offering to pay, make that offer up front: “Can I take you to ____ tonight? Dinner’s on me.”  (This is a good thing to do anytime you are treating a known poor-er person, the anxiety of guessing and mentally running the budget numbers is just awful and fun-destroying). When you are splitting costs or expenses, settle up right away. “The bill is ______, do you want the waiter to split it for us or do you want to pay and I can Venmo (etc.) you my half?”

This may seem unromantic and tedious, and it might bring out some weird shame behaviors and avoidance in him, but do it anyway. If you can’t afford something, say so. “That sounds nice but pricier than I can handle right now, can we save it as a treat for next month and stay in tonight?”  Make this shit matter-of-fact and normal. Make yourselves a couple who can talk frankly about money in mundane, routine ways that doesn’t require big negotiations or emotional processing.

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Thank you all for the kind words and end-of-year donations and patronage that have flowed in over the last week or so. I’ve been traveling and kind of made a point about not touching my laptop for a week or so, but I read everything and I’m very grateful. ❤

Everyone’s doing decade-retrospectives and my brain is melting at the thought of it. Ten years ago, I was still technically a grad student/adjunct teacher, I lived with roommates, I’d just finished my very last student film, Captain Awkward Dot Com didn’t launch until January 2011, and I didn’t meet Mr. Awkward until 2012.

But let’s do a 2019 round-up, yes? Here were the most-viewed/shared/discussed posts from the site in 2019:

First, a timely seasonal carryover from the very end of 2018,  “#1162: Is there room to compromise when it comes to alcohol and driving? (Answer: Why not set the default at “Don’t drink and drive”? I made a chart and everything.)

Next: #1215: ” ‘So…about your private reproductive decisions’ and other ‘small’ talk.” 

Let’s please stop asking people about their intense private life stuff out of passing curiosity, the idea of politeness, or because we think we’re entitled to know. When people have big news about babies, THEY’LL TELL U.

While the rest of the world catches up, this post has lots of strategies for answering (and deflecting/de-escalating) potentially fraught “small-talk” questions that can unknowingly hit real sore spots.

P.S. Letter Writer #1228 you’ve been in my thoughts and the offer to fight your family in real life if necessary is still incredibly open.

Third, #1219: “My friend’s boyfriend keeps ‘negging’ me.” 

This post has THREE HUNDRED AND EIGHTY ONE comments strategizing about whether it’s okay to tell a serially annoying dude “Look, could you stop?” and is often re-shared/cited for mention of “Schrödinger’s Autist,” a theoretical construct who only comes out in Internet discussions of cis men behaving badly toward women as a way to pre-excuse bad behavior (and has nothing to do with actual autism).

Fourth-most viewed is #1186: “How do I restore trust in my relationship?

Like the faux rank of “Captain” Awkward, “The Marie Kondo of Breakups” is a self-assigned comedy title because it’s one of my life’s missions to tell my younger self young people, especially young women, that a partner who keeps letting you down and leaving you wondering in the early stages of a relationship is probably not going to change for the better, and there’s nothing you can do to “love somebody more” into being who you need them to be.

It’s okay to want love, to risk, to try to make things work, but working at somebody who isn’t doing any work to be a good partner to you is a lonely and disappointing bet.

Fifth, #1218: “Irritability and constant criticism in a marriage. The post and comments are a good roundup of previous discussions of verbal abuse and safely extricating oneself from a draining and damaging partnership.

Good “Could this be abuse?” guideline: When someone who is supposed to love you is constantly mean and you start asking yourself “what’s wrong with me that’s making this person be so mean, how can I fix myself?” it might be time to visit LoveIsRespect.org from a private browsing window and start making plans.

Sixth, #1198: “How do I deal with work burnout and make my partner* happy?” (*My partner = my boss, who is *a* partner in the law firm where I work)

Notable for link to description of “insecure overachievers”and how capitalism hijacks anxieties and perfectionism in search of star performers, not caring who burns out along the way or how unsustainable and unhealthy the culture can get.

VERY GOOD NEWS: This Letter Writer sent me an update and is doing MUCH, MUCH, MUCH BETTER. ❤

Seventh, #1197: “He broke up with me but hasn’t moved out yet. How do I not ruin our last chance to make this work?” 

I had the worst time moving on after breakups (rejection sensitive dysphoria, yaaaaaaaay) and learning how to let people go was one of the hardest and best lessons I ever learned. I’m proud of this heartbreak omnibus and hope it can make a difference to others. There are enough ballrooms in you, Letter Writer, and I hope you are in much better straits now.

Eighth, #1194: “I’m moving in with my girlfriend and now my homophobic parents want to disown me. One of a series of posts on family estrangement and how to close doors to protect yourself and leave some open in hope of better things. “Forever is a long time, Sally.” Letter Writer, your parents don’t deserve you and I hope your new home with your girlfriend is a cozy and happy one that is everything you want it to be.

Ninth, #1233: “Is it ever safe to take a parent off a low-information diet?” 

People have choices about how they treat you, and relationships don’t get messed up overnight or for no reason, so when a parent wants you to have a “closer” relationship, does that obligate you to try to repair things in some way? Can they acknowledge why distance made sense at the time?

Probably one of the most personal posts I’ve made on the site, this brought up lots of stuff for me and was very much on my mind during holiday visits with my folks. When people talk about the past, my mom says “I don’t remember that” a lot ( A LOT) in a sharp, pointed way that clearly means “So, obviously it didn’t happen.” She’s telling the truth (she doesn’t remember) but it doesn’t mean that it didn’t happen or that my memories are lies. I still don’t know how to ever ethically tell our story or tell her about my writing here, but I know our story lies at the heart of many of the things I write here.

In tenth place, several posts around the topic of “WEDDINGS, WHY ARE THEY SO WEIRD?” came in within 100 page views of each other so I’m re-sharing them all:

  • It’s Mother-Effing Wedding Season Again So Let’s Chat. Your wedding doesn’t exist to fix you, your family, your friendships, your partnership, your body. It does not have to be your sole creative act that communicates your exact social class and crafting ability.
  • #1223: “Feminist Etiquette Wedding Help”. Your wedding doesn’t exist to fix you, your family, your relationship, your body, or the world. It’s a party so try to throw a good one that makes you happy and invites your guests in to what you want vs. trying to argue with each of them about why you’re allowed to want what you want. “Oh thanks, but we’re all set!” is a very useful phrase.
  • #1188: “Grief and empty chairs at the wedding feast.Maybe the idea of ghosts first sprang from the divided vision of grieving people, the way we can both see the party as it’s happening and see the echoes of what the party should be like, our longing giving shape and color to the empty spaces where our loves should be.”
  • #1189: “Fox News, Immigrant Family, and the F**ing Wedding Invite List.Probably the Uncle could have behaved himself for one day, but this thing where we tiptoe around bigots and keep negotiating with non-bigots for “more tolerance” toward bigots has gotta stop. We can work on tolerating/convincing/courting them once we’ve out-organized and out-voted them, let people who aren’t their direct targets run interference for a change.

I should also highlight the awesome series of guest posts from Lenée aka dopegirlfresh aka the GOAT who filled in for me during surgery in the spring. I plan to have her back in 2020, as well as some other exciting guests (Rae McDaniel has volunteered to peek into the inbox to answer questions about gender, we’re just trying to get a meeting on the calendar to figure out the logistics).

The blog motto for 2019 was “Quit working so hard on relationships that aren’t working for you” and I’m still ruminating on 2020’s. How do people feel about “Do even less work than that and see how you feel?”

Love and good New Year wishes to all of you in Awkwardland, comments are open.

Got an update for us (never an obligation, but we love to read them)?

Is there a post from the past year that you found especially useful?

Did you kick ass at setting a difficult boundary this year?

Did you decide to put in “less work” with a thorny relationship? What happened?

Hi Captain!

I’m an adjunct professor at a mid-sized University, a new mom, and I just had a very awkward encounter with my department head. I’m teaching one of the sections of my department head’s courses; so myself, the department head and all the other section instructors meet up each week to discuss things and make sure we’re on the same page. Before the semester started, I emailed her to let her know that I recently had a baby and if there was a place I could pump between our course meeting and the start of class. She responded that I was welcome to use her office anytime (I don’t have an office) and to let her know if I needed anything. Great! Fast forward to the first day of class: we have our course meeting and all is going well. At the end of the meeting, I ask my department head if now is convenient for her to lend me her office so I can pump; and if not, I’m happy to wait until she’s ready. She enthusiastically responds that now is a great time and that she’s totally comfortable “being around exposed boobies.”

I’m a bit taken aback at this point, I expected I’d be able to pump privately. I start mumbling about not wanting to interrupt her work when another one of my fellow adjuncts comes to my rescue and informs me the adjunct lounge is currently empty and the door has a lock. I’m relieved and my department head cheerfully remarks that’s the perfect place to pump. I make my way over to the adjunct lounge, lock the door and get to work. Five minutes later, I hear a knock on the door… it’s my department head. She whispers through the door to be let in, saying she has something important to discuss with me. Unnerved, I unlock the door and let her in. At this point, I have all my pumping gear on and am wearing my pumping bra, so I’m mostly covered up, but my shoulders are bare and one can clearly see my pumping bra. My department head looks at me for a moment, then asks me if I’ve seen where one of the other adjuncts has gone. Umm….what? She could have asked anyone else in the hallway that question, why did she have to come in and ask me? I’m clearly super uncomfortable and I respond that I haven’t seen her since the meeting. My department head stares for another moment, then apologizes profusely for disturbing me and leaves.

My question is: what on earth should I do about this? I’m incredibly uncomfortable with how she conducted herself, especially since she’s my boss. Should I speak to her about this? What should I say? Should I just pretend this never happened and hope it doesn’t happen again? I’m definitely not going to use her office to pump (or pump anywhere in that building if I can help it).

Thanks!
Awkward Academic (she/her/hers)

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Dear Captain Awkward,

Yesterday night, seemingly out of nowhere, my husband “Andy” (he/him) got a message from a friend of ours, “Marc” (he/him). In this very long message, Marc wrote that he felt hurt and attacked by Andy during his recent (2-3 days ago) visit to our house. Marc used words like “venomous” and “vitriol” to describe Andy’s “ceaseless attacks” on him from the moment he came home that reminded him of how he (Marc) was bullied and abused as a child. Marc ended the message by saying he has always valued Andy’s friendship and hopes Andy would tell him if he’d done something to upset him. Andy called Marc twice last night and once this morning, in addition to sending him a message but got no
response. I also called Marc but he didn’t pick up my call either.

Some background. We are all in our late thirties/early forties. We met Marc through a mutual friend about 5 or 6 years ago, and both Andy and I have been friendly with Marc, especially for the last 18 months that we have lived in the same city. Marc comes over to our house once a week, and usually hangs out for most of the day. Marc is independently
wealthy and would like to do more travel, outings, etc. but Andy and I both work and are trying to save money to start a family, buy a house, etc and usually aren’t up for it. We’ve always enjoyed hanging out with Marc. He was at our wedding! I think both Andy and I would describe him as one of our closest friends in the city.

The message really hit Andy hard. Andy is one of the kindest, most considerate people I have ever met who will bend over backwards to help people. This is not just wifely bias, but lots of people, even acquaintances/colleagues will say that about him. It’s possible that Andy maybe made a joke or comment that hurt Marc’s feelings but nothing rising the level of the constant, vitriolic attacks that Marc describes. Andy wanted to get in touch with Marc to get some examples of what he said wrong so he can apologise and not hurt him like that again. Despite saying he values the friendship, Marc is refusing to
engage with us.

So here’s the tricky part. For the past couple of months, I’ve gotten a feeling that Marc may have a crush on me. It’s little things that are easy enough to ignore, complimenting the way I look or the food I make, suggesting a time to hang out when he knows my husband will be working. Nothing substantial but you know how women sometimes just
have a sixth sense for when men are flirting. Like you just know? I never said anything to Andy because a) Marc was never inappropriate with me, b) I enjoyed Marc’s company and so did Andy, c) people have crushes and I figured it would fade and things would go back to normal. Now I’m wondering if Marc is purposely burning the bridge or got upset with Andy because of feelings for me? Ahhh, even writing that makes me feel so stuck up. I promise I don’t think everyone is in love with me.

Two questions: What should Andy and I do, if anything to try to address this with Marc?Should I be honest with Andy about my theory on Marc’s behavior?

*I read your rules and I swear I’m not simply doing emotional labour
for my husband, but I feel like this is my problem too.

(She/Her)

Hi there,

I’m sorry you’re dealing with this. I’m going to suggest, bluntly:

Let Andy & Marc work it out (or not). Do not attempt to mediate, explain, intervene, or search your soul for reasons a man is behaving badly and how you might have caused it or somehow affect the outcome. Question of the century: What if we collectively stopped pretending that volatile and hostile men are everyone else’s problem to fix?

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