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?
This seems like a really simple problem but nothing at the intersection of booze, shame, love, and money is ever that simple.
You could start putting in cash for your tab and leaving earlier than he does, so you’re not the one covering for him. If you do this, you could hand your friend the money and make her the Keeper/Counter of the Money, like, “I’m out, this covers me, see you next week.”
You could bring it up privately with your friend – “This is awkward, but I’ve noticed that at the past few Trivia nights, Boyfriend hasn’t put in quite enough for all of his drinks and the rest of us have ended up covering it.” Your friend will most likely be mortified and either talk to the dude about cutting back on his intake or working out a system where she treats him. Either way, she/they will handle it between themselves and it won’t be your problem anymore. This may be the beginning of a “Also, Friend, is he ok and are you cool with how much he’s been drinking lately?” conversation or it may not. Be ready to listen, but initially keep the conversation focused on the math.
You could bring it up (or someone in your group could bring it up) at the moment that he puts money down before he leaves, especially if there someone in your group who usually is the Keeper/Counter of the Money, like, “Hey, something’s not right, that’s only $20 but beers are $4, so it’s more like $30.” “Whoa, did you forget to pay? Let’s get your keys while we’re at it, too drunk to pay is definitely too drunk to drive.” You could talk to him directly about it, like, “Hey, I don’t want to embarrass you, but I’ve noticed the tab was short last time, so can you make sure you put in enough tonight? We can help you with Drunk Math if you need. And also, you’re not driving right now, are you?”
I think a compassionate strategy is to treat it like an honest mistake – “You/He probably didn’t realize, but now that you do, it surely won’t be a problem anymore!” If it was a mistake, the person now has the information to correct that mistake delivered in the least mortifying way possible. If it’s still a problem going forward, then you’ll know that it wasn’t an honest mistake.
The things that stand out to me from your letter are the anxiety that your friend would be angry with you if you brought this up or that this would somehow ruin their relationship. If she’s angry with you (instead of with him) for saying something, that’s a sign that things are not all the way okay in that relationship and I can see why you are reluctant to poke at it in case that’s the truth. However, it’s okay to not want to cover this dude’s bar tab every week, whether it’s down to sleaze or obliviousness. It’s sweet that you want to not embarrass the guy, but getting annoyingly drunk and then running out on a bar tab week after week is embarrassing stuff! I would be very embarrassed if I were doing that, as would you! You’re experiencing proxy shame and awkwardness on his behalf, and it’s time to return some of that where it belongs.