Dear Salty Waitress: A couple weeks ago, I went away on a girls’ weekend for my friend’s 40th birthday. The group included people I know well, as well as some women I had only met a few times. We paid for the big stuff up front: hotel, wine tasting trip, etc. But over the course of the weekend, each of us picked up the tab for smaller expenses, like snacks at the winery or an Uber trip or some coffees.
Then, a couple days after the trip, I got a series of Venmo requests from one of the women. She requested I pay her back for—I’m not shitting you—a $4 latte, my $5 portion of the cheese plate, etc. It only added up to about $20, which I guess I’ll pay, but this just seems totally tacky to me. I paid for some small stuff, too, with no expectation of being reimbursed.
We are all adults, and it seems like these smaller expenses are to be expected in the course of the weekend. Am I reasonable to think this is tacky, and should I do anything different next time I’m out with this woman and the bill comes around?
This is why I avoid group vacations like the plague. (That and because I would rather not see friends of friends in white string bikinis.)
So honey, to your first question—yes, I find her request tacky if you all covered roughly the same amount of minor expenses. When you’re in a group of more than three, it definitely makes a cashier’s life easier if just one person pays for the coffees or ice creams or wine or what have you. You’re adults, and after a whole weekend, you’d expect it to come out in the wash. Resist the temptation to request money from her back for the food you covered—take the high road, I say.
As for what you can do next time around… never see her again? Kidding. Maybe. But if she’s good friends with your friend, I guess it’s likely you’ll have the pleasure of her company in the future. If it’s another group-dining situation where there’s bound to be sharing and wine and some separate appetizers yada yada, you could try to bring it up ahead of time. But, you know, be classy about it: “Are we all comfortable splitting the check evenly? Who knows, I may have one more glass of wine than someone else.” (In your dream world, Claire or whatever her name is will recognize herself in this. In reality, she won’t.)
Some people just can’t bear to spend one dime more than they think they should, no matter how well-off they are. You can either try to avoid her company altogether, or just order your own, non-sharing food when she’s around.
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