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?