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Dear Captain Awkward,

I have a great, strong, smart female friend who has fallen head over heels for her boyfriend. They’ve been dating for under a year but already live together.

This friend has been attending a weekly trivia night with us now for over a year. When the new guy came on the scene he said how much he loved trivia and asked to join. We are a very inclusive team with friends from all over so of course we let him.

While he isn’t the favourite at trivia (he is very competitive and we are very bad at trivia but we have fun) things had been mostly fine, until he lost his job. He has been unemployed now for about 4 months, which I get is tough. However, he went from having a few beers at a casual Monday trivia to having 6+ over the course of 2 hours.

It’s awkward when he gets drunk for sure, but again I could have put up with this. I get it being sad about not having a job is hard. However, in the last month there has been a pattern of him not paying for said drinks. The bar we go to refuses to do separate tabs, so what often happens is people put their cash down and go. Consistently it seems he doesn’t put enough in or any at all, and by the time we realize those of us who are left are stuck with the bill. It’s one thing to forget once or twice, but it seems to be a pattern.

I’m not really sure what to do. I don’t want to embarrass him, and I don’t feel we are good enough friends for me to confront him about it. But I also know my best friend wants to spend the rest of her life with this man, and I’m worried that if I bring it up she’ll get angry with me. Money is such an awkward subject, what do I do?

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Dearest Captain,

I have had a rough few months in which I have temporarily moved home to deal with a highly stressful situation. The crisis itself has largely passed, but I’ve decided to stick around for the holidays, since I do love my family and they don’t seem to mind me crashing with them for a while longer.

The most prominent issue in my life right now is with one of my new friends in my new state. He’s a nice guy and all, but he’s kind of…irritating. I didn’t say much to him before I left to go back home, but he knows that there was an emergency and that I’d be out of town indefinitely. Since I left, he hasn’t stopped pestering me to ask me how I’m doing (crisis situation, wtf does he think?) and sending me pictures and motivational quotes in the name of trying to cheer me up at least once a week. The latest was a picture of a rainbow intended to “Brighton [sic] your day!”

I’m aware that there are far worse problems to have, but he’s driving me nuts. I haven’t responded to him in nearly two months because of other priorities, including not wanting to get sucked into a drawn-out conversation I don’t have the energy for, and he is damn near impossible to shake once he’s got any sort of handhold. However, he’s also damn near impossible to shake even after two months of silence on my part, go figure.

I feel like I’m on the other side of Letter 366, where I’ve got the avoidant attachment style, and the harder people cling, the harder I push them away. I consider myself very independent, and I know that’s feeding into this as well…if I’m going to be cheered up or have my day brightened, I want it to come from within, when I’m ready to start feeling better on my own. My close friends know to let me wallow in self-pity until I arrive at a more balanced frame of mind on my own.

Is it all right to tell him, “Don’t call me, I’ll call you?” I’m not necessarily sure I want to cut him out of my life entirely, but I am sure that I need him to drop the contact attempts way back and make the ones he does send less saccharinely feel-good.

-Let Me Mope in Peace

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I’m a 17 year old homeschooled dual-creadit student who attends my local community college. I have a 4.0 there, and I am part of the honor society and an officer in the Honors Student Organization. I’m not, at least not in by my family’s standards, brilliant, but I am smart. I always try to be a nice person and do good things, but I am worried that I come off as condescending and sometimes bitchy to my class mates. My grades are a large part of my identity because I am so focused on school, and because of that I have a reputation as an overachiever in all of my classes. I use my reputation as, at least somewhat, a defense mechanism. I have never had a boyfriend, had any alcohol,done any sort of drugs, etc. The people in my classes call me a baby because I don’t lie about being extremely inexperienced, and I don’t really mind that. I my be inexperienced, but I am not as naive as they seem to think I am. I use my inexperience as a reason I don’t throw parties when my parents leave me home alone for sometimes up to a week (they both travel for work). I don’t hide my grades from my fellow class mates; in fact, I share them openly. However, sometimes I worry that I come off as condescending because a lot of people make Bs or Cs, which I consider failing for me. I know that considering that a B is failing isn’t healthy, but school is my life and I don’t know how to let it go. I generally don’t understand why people don’t try hard in school and do their best. I understand that a lot of people have a job, kids, or both; but those aren’t really the people I’m talking about. The people I don’t understand are the ones that complain about doing poorly on tests and having to drop classes and then do to festivals on the weekend when they have homework. I also know that sometimes I can see the world in too much black and white and not take into account the environment somebody grew up in. I want to understand them better, but it is so much easier to call them stupid and write them off in my head as a lost cause. How do I learn to think of people as people and try to understand where they are coming from? When should I stop giving them leeway and say they need to step up and try harder? How do I not let my school define myself and my life when they are so important to me? How do I/ should I hold back on what my grades are because I may come off as a insensitive and condescending? Why do some people ignore their school and then freak out because they are failing?

Thank you for your time,
– The Overachiever

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Dear Captain Awkward:

I’m in my late sixties, and I have some health challenges that mean I’m occasionally caught short and need to use the ladies’ room rather urgently. This happened to me earlier today in a restaurant, where I was in the (single) ladies’ room for about ten minutes. After I’d been in for one minute, someone came and pounded (like, with the side of a closed fist) on the door. I said I’d just be a few minutes, and the pounding stopped. For about another minute, after which time it started up again. I said I was sorry, but that I’d only be a few minutes. I get that I’m not the only one in the world with this issue, but I was being as quick as I could. Really, I was helpless to leave at that point, if you know what I mean. When I was able, I completed my business, washed my hands, and opened the door, to find a woman of thirty-odd standing in the hall with a scowl and a raised fist. “There are four people out here waiting to get in there!” she snarled. (I looked. There weren’t.) “Maybe you should have used the men’s,” I said. “Instead of standing there arguing, why don’t you just get the hell out!” she said. Very loudly. People were looking, though they were trying not to meet my eyes. And I’m not proud of this, but I said, “Why don’t you go fuck yourself?” and collected my coat and purse in a leisurely fashion while she reared back and gave a Victorian-maiden impression over my use of the f-bomb. Nobody in the place would look at me as I left.

I don’t feel like I can ever go back to that restaurant, which is unfortunate, since they make a great scallopini. I feel humiliated, and I feel powerless, because that was the only comeback I could think of. What should I have done?


Dear IBS in CA,

You could have said “WOW” or “EXCUSE YOU” but I think you should take a page from Dame Helen Mirren, who regrets not telling people to “fuck off” more in life.

I feel bad for that lady, in exactly one respect, in that she probably had to use the bathroom really badly and was not her best self in that moment. However, that’s not your fault, abusing you was not the answer, and you don’t have to care about her feelings. Let her clutch her pearls forever while you go back to that restaurant any time you feel like it and eat some scallopini.

Let’s take this as yet another argument in favor of gender-neutral bathrooms.


Captain Awkward

Hi Captain,

A bit of backstory: last spring, Fiancée and I (both US citizens) returned to the US from Europe, where I had been working and she was going to school. My parents offered to let me stay with them while I looked for a job, and Fiancée went to stay with her mom several states away.

My mother has decided that Fiancée is a directionless gold-digger with no career prospects (Fiancée is a former professional ballerina who is now working on a degree in rehabilitative physiotherapy), and has also accused her of giving me an STD (apropos of nothing). Obviously, this makes the topic of Fiancée somewhere I’d prefer not to go, since it turns into a stream of baseless accusations (and then veiled threats if I try to refute them).

Now that I’m employed again (yay!), I am moving into my own place again. Having gone to university Far Away and worked for five years somewhere Even Further Away, most of Team Me isn’t accessible to help with the move, so my parents are helping me out. The problem is that my mom feels that if Fiancée moves in with me, this proves that Fiancée is a leech for not helping with the move. I get my mom’s point– it’s obnoxious to have someone reap the benefits of your hard work. My extended family, who I’d thought of as Team Me, agrees with her (and helpfully relayed to her that we’d had a conversation! Because the concept of a private conversation is lost on them, and now).

After some silent treatment after hearing from my extended family, my mom decided to offer to talk. Given her past behavior, I do not believe this will be a productive conversation– she is the master of derailing, belittling, gaslighting (‘I never said/did that! You’re clearly delusional/making things up!’ or ‘you just have a skewed perception’). But now if I outright refuse to engage, I’m 100% the bad guy, not just with her but with my extended family (‘I tried to talk, and she just ignored me!’).

How on earth do I navigate this drama bomb minefield with a minimum of stress and family awfulness?

-Want to Quit Drama Llama Farming

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Dear Captain,

I recently started dating a guy I really like. He’s a techie and most of his friends are friends from work. They do a lot of social stuff together. He’s been great about introducing me to them and inviting me to things like happy hours, which is important to me after having dated two guys who pretty much refused to introduce me to anyone else they knew for Reasons They Could Certainly Justify.

So, that’s great, right? Except hanging out with them is quickly becoming excruciating. I am not a shy person and am a pretty good conversationalist – hell, my JOB is making people feel comfortable and welcome and I spend a lot of time having dinners with people in my industry where I’m pretty much there to hear them talk about work and convincingly feign being fascinated.

What will happen is that he’ll extend an invitation, I’ll accept, and then I’ll spend anywhere from 1 to 5 hours staring at my plate or glass of wine while they talk about work. Constantly. Nonstop. If it’s not the highly technical details of whatever program they’re working on now, it’s dissecting everyone else they work with. I’ve tried gently steering the conversation towards not-work topics and contributing where I can (limited, because 1. I don’t know the people they’re referencing and 2. I don’t work in the tech field) and I’ve not been successful.

After the last outing, I asked him if hanging out with his friends = all work talk all the time? And he seems vaguely apologetic but also like yeah, this is how it is and will always be.

So. He’s spent time with my friends, most of whom are not people I work with, and we’re all able to have lively conversations about things we’re all interested in – not rehashing all the inside jokes from the last tech convention that only those who attended would get.

Applying the Sheelzebub Principle, if I have to put up with this for a few more months, much less 5 years, I will lose my mind. But I do like this guy and I want to give this a chance (I have been known to hit the eject button on new relationships very quickly in the past).

Thoughts? It’s important to me to be on good terms with his friends, even if I’m not interested in making them my friends, and he does a lot – a LOT – of socializing with them. I’m hesitant to bring this up with him because it will make me feel like that Whiny Girlfriend Who Doesn’t Understand Coding and wants everyone to dumb things down for her sake, which is not the case, and I also get that he does not control their behavior (although he certainly isn’t helping things when we’re in this situation, because he’ll sit there and do the All Work All The Time Channel too).

I get that some of these people probably are used to not having others understand what they’re talking about, and there is a fair amount of on-the-spectrum-y, social awkwardness going on here, but I come from a family of peeps with autism and actually worked in the engineering field for a while, so I consider myself pretty good at empathizing and interacting with people who might, for certain reasons, be a little wrapped up in explaining to you how the widget works, even if you’ve no interest.

– It’s Ok to Talk To Me Even if I’m Not a Programmer

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