Personal-finance columnist Charlotte Cowles asks the nosy, revealing, sometimes uncomfortable questions about money so you don’t have to.
Photo-Illustration: by The Cut; Photos: Getty Images
Hanging out with friends is good. Simmering resentment over shared costs is not. We recently asked dozens of readers to share awkward financial scenarios they’ve encountered within their social circles. And you had some things to get off your chest! How to prevent difficult, petty exchanges when you’re out spending money as a group? For starters, try to avoid — or at least be aware of — the following traps.
You’re saving up points for a trip? Good for you — so is everyone else. “I have one friend who’s always like, ‘I’ll get the bill, Venmo me later!’ and makes it seem like he’s doing us this big favor, which is annoying because we know he just wants the airline miles. So do I!” says Tara, 27. “Recently, another friend made a joke out of it, and the points guy got offended and said we didn’t respect his financial situation. Apparently he needed the points for a plane ticket home at Christmas.” Okay! But so might other people. Bottom line: You’re not the only one with a credit card. Ask if anyone else is eager for the benefits before you snag them for yourself.
In general, ask your friends if they’re comfortable paying for something before you assume they will — it’s easier than you might think. And if something weird goes down when you’re out together, clear the air before you settle up the bills.
For instance: “A friend asked me to meet her and her mom for drinks when her mom was visiting. They don’t get along super-well, so she wanted a buffer, and I figured I’d do her a favor,” says Peter, a 39-year-old living in Texas. “When I showed up, my friend, her mom, and my friend’s random Tinder date — someone I’d never met before — were all there. I left early because it was so awkward.” The next day, Peter’s friend sent him a Venmo request for the drinks, which he ignored; he felt she had been disrespectful of his time and friendship, but it turned into a fight about money instead. “When I didn’t respond, she called me a freeloader,” he says. “I haven’t spoken to her since.”
Cost-sharing apps like Venmo and Splitwise can be a godsend for group expenses, but be sure you’re on the same page before you start uploading receipts. “Last year, I spent a weekend with friends who wanted to put everything on Splitwise. Which is fine, but like … if you bring a bottle of wine to share, do we all have to pay for 1/6th of it?” asks Christine, 36.
Also, not everyone is comfortable using it. “I invited friends to the Hamptons for the weekend and one of them suggested we use Splitwise to track what we spent/owed. It seemed like a good idea at first, but it ended up making things more complicated,” says Dani, a 35-year-old in New York. “There was also a limit on how many receipts we could upload in a day. It created a hilarious tension between the friend who suggested we use it and the rest of us being like, ‘I hate this app.’” The takeaway: If you want to use a different system — like setting up a group “kitty” that everyone contributes to equally — make your pitch. But don’t complain once the plan is in motion.
No one likes to quibble over who ordered what, but it’s important to respect that certain people may not want to pay for certain things. “I’m a vegetarian, and when I go out with friends it sometimes feels unfair to split the bill down the middle for my $15 vegetarian entree when they ordered a $50 surf-and-turf thing,” says one woman from Chicago.
On a related note: “I went to a bachelorette party in the Hamptons and the bride bought a bunch of cocaine and added it to the Splitwise,” says Andrea, 40, of Philadelphia. “Several of us did not partake. I still think it was rude that we had to pay for it.”
The same goes for some nondrinkers. “No one likes a judgmental sober person, so I don’t want to draw attention to the fact that I don’t drink when I go out,” says Daria, 26, from South Carolina. “Most of my friends are conscious about it and offer to cover my Diet Cokes. But I have one friend who drinks a lot — definitely too much, but I was that person before I got sober, so I empathize — and is constantly splitting the bill equally between everyone. I’ve probably spent hundreds on her drinking habit at this point, which sucks.”
Ideally, you want to address these disparities before you look at the menu. (A simple “Do you mind if we itemize the bill?” is all it takes, and the Tab app makes it fairly easy.) If you don’t, confrontations can get ugly. “A few weeks ago, my friend drank a bottle of wine by herself when we were out in a group,” says Daria. “Another friend pointed it out, because she didn’t want to pay for it, and the drunk friend kept insisting that we all shared it. It was an argument about money that was actually an argument about her drinking. We wound up splitting the bill just to get it over with, but I think I’ll be discreetly requesting separate checks going forward.”
“I used to work in restaurants, so I know it’s a huge pain for the servers when a big group asks for a bunch of separate checks,” says one reader in Chicago. “When I’m going out with people, I think it’s best to alternate who’s paying. Or, if it’s really expensive, we’ll settle up on Venmo after. When people ask to itemize at the table, I would rather pay for the whole bill myself.”
Generosity is in the eye of the beholder, and not everyone feels grateful when someone else picks up the tab. “I have a friend who comes from a wealthy family, and she’s always paying for stuff when we go out. At first it was nice, but then it started to feel a little insulting. Like, I’m 31 years old. I get that she’s rich, but I can pay for my own meal!” says Danya, a consultant in New York. “I also hate feeling like I owe her all the time — it makes our friendship feel fundamentally uneven. When I offer to pay, she just waves me off. I don’t know how to address it.”
In other cases, offering financial help can bring up a sore subject, which is why it’s best to tread carefully. “I went on a bachelorette trip with a friend of mine who had recently been laid off,” says Andie, 32, from San Francisco. “I figured she might be in a tough spot because she’d agreed to the trip before she’d lost her job, so I reached out and asked if I could help her cover some of her trip expenses. She got super-offended and said no. I guess I touched a nerve, and I felt terrible. I was just trying to be a good friend!”
Maybe your wealthier friends don’t notice or care that you’re making the most of their largesse. But other people might. “I have rich friends, a couple, who host groups frequently at their beach house,” says Molly, 40, who lives in Brooklyn. “I try to bring a nice gift and pay for wine/groceries/incidentals. But I once witnessed another friend who, while checking out at the wine store, called to our host and said, ‘Come here, we need your credit card!’” The hosts didn’t object, says Molly, probably because the bill wasn’t a big deal to them. “But it still shocked me and made me wary of the other guests.”
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