![](\"https:\/\/www.europesays.com\/us\/wp-content\/uploads\/2025\/08\/b8e1c9a61ec0b86dffcd81febbb173f130-My2Cents-Aug14.rsquare.w400.jpg\")
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My Two Cents<\/a><\/p>\n \n Personal-finance columnist Charlotte Cowles asks the nosy, revealing, sometimes uncomfortable questions about money so you don\u2019t have to.\n <\/p>\n \n Photo-Illustration: by The Cut; Photos: Getty Images\n <\/p>\n 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\u2019ve encountered within their social circles. And you had some things to get off your chest! How to prevent difficult, petty exchanges when you\u2019re out spending money as a group? For starters, try to avoid \u2014 or at least be aware of \u2014 the following traps.<\/p>\n You\u2019re saving up points for a trip? Good for you \u2014 so is everyone else. \u201cI have one friend who\u2019s always like, \u2018I\u2019ll get the bill, Venmo me later!\u2019 and makes it seem like he\u2019s doing us this big favor, which is annoying because we know he just wants the airline miles. So do I!\u201d says Tara, 27.\u00a0\u201cRecently, another friend made a joke out of it, and the points guy got offended and said we didn\u2019t respect his financial situation. Apparently he needed the points for a plane ticket home at Christmas.\u201d Okay! But so might other people. Bottom line: You\u2019re not the only one with a credit card. Ask if anyone else is eager for the benefits before you snag them for yourself.<\/p>\n In general, ask your friends if they\u2019re comfortable paying for something before you assume they will \u2014\u00a0it\u2019s easier than you might think<\/a>. And if something weird goes down when you\u2019re out together, clear the air before you settle up the bills.<\/p>\n For instance: \u201cA friend asked me to meet her and her mom for drinks when her mom was visiting. They don\u2019t get along super-well, so she wanted a buffer, and I figured I\u2019d do her a favor,\u201d says Peter, a 39-year-old living in Texas. \u201cWhen I showed up, my friend, her mom, and my friend\u2019s random Tinder date \u2014\u00a0someone I\u2019d never met before \u2014 were all there. I left early because it was so awkward.\u201d The next day, Peter\u2019s 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. \u201cWhen I didn\u2019t respond, she called me a freeloader,\u201d he says. \u201cI haven\u2019t spoken to her since.\u201d<\/p>\n Cost-sharing apps like Venmo and Splitwise can be a godsend for group expenses, but be sure you\u2019re on the same page before you start uploading receipts. \u201cLast year, I spent a weekend with friends who wanted to put everything on Splitwise. Which is fine, but like \u2026 if you bring a bottle of wine to share, do we all have to pay for 1\/6th of it?\u201d asks Christine, 36.<\/p>\n Also, not everyone is comfortable using it. \u201cI 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,\u201d says Dani, a 35-year-old in New York. \u201cThere 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, \u2018I hate this app.\u2019\u201d The takeaway: If you want to use a different system \u2014 like setting up a group \u201ckitty\u201d that everyone contributes to equally \u2014 make your pitch. But don\u2019t complain once the plan is in motion.<\/p>\n No one likes to quibble over who ordered what, but it\u2019s important to respect that certain people may not want to pay for certain things. \u201cI\u2019m 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,\u201d says one woman from Chicago.<\/p>\n On a related note: \u201cI went to a bachelorette party in the Hamptons and the bride bought a bunch of cocaine and added it to the Splitwise,\u201d says Andrea, 40, of Philadelphia. \u201cSeveral of us did not partake. I still think it was rude that we had to pay for it.\u201d<\/p>\n The same goes for some nondrinkers. \u201cNo one likes a judgmental sober person, so I don\u2019t want to draw attention to the fact that I don\u2019t drink when I go out,\u201d says Daria, 26, from South Carolina. \u201cMost of my friends are conscious about it and offer to cover my Diet Cokes. But I have one friend who drinks a lot \u2014 definitely too much, but I was that person before I got sober, so I empathize \u2014 and is constantly splitting the bill equally between everyone. I\u2019ve probably spent hundreds on her drinking habit at this point, which sucks.\u201d<\/p>\n Ideally, you want to address these disparities before you look at the menu. (A simple \u201cDo you mind if we itemize the bill?\u201d is all it takes, and the Tab app makes it fairly easy<\/a>.) If you don\u2019t, confrontations can get ugly. \u201cA few weeks ago, my friend drank a bottle of wine by herself when we were out in a group,\u201d says Daria. \u201cAnother friend pointed it out, because she didn\u2019t 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\u2019ll be discreetly requesting separate checks going forward.\u201d<\/p>\n \u201cI used to work in restaurants, so I know it\u2019s a huge pain for the servers when a big group asks for a bunch of separate checks,\u201d says one reader in Chicago. \u201cWhen I\u2019m going out with people, I think it\u2019s best to alternate who\u2019s paying. Or, if it\u2019s really expensive, we\u2019ll settle up on Venmo after. When people ask to itemize at the table, I would rather pay for the whole bill myself.\u201d<\/p>\n Generosity is in the eye of the beholder, and not everyone feels grateful when someone else picks up the tab. \u201cI have a friend who comes from a wealthy family, and she\u2019s always paying for stuff when we go out. At first it was nice, but then it started to feel a little insulting. Like, I\u2019m 31 years old. I get that she\u2019s rich, but I can pay for my own meal!\u201d says Danya, a consultant in New York. \u201cI also hate feeling like I owe her all the time \u2014 it makes our friendship feel fundamentally uneven. When I offer to pay, she just waves me off. I don\u2019t know how to address it.\u201d<\/p>\n In other cases, offering financial help can bring up a sore subject, which is why it\u2019s best to tread carefully. \u201cI went on a bachelorette trip with a friend of mine who had recently been laid off,\u201d says Andie, 32, from San Francisco. \u201cI figured she might be in a tough spot because she\u2019d agreed to the trip before she\u2019d 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!\u201d<\/p>\n Maybe your wealthier friends don\u2019t notice or care that you\u2019re making the most of their largesse. But other people might. \u201cI have rich friends, a couple, who host groups frequently at their beach house,\u201d says Molly, 40, who lives in Brooklyn. \u201cI 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, \u2018Come here, we need your credit card!\u2019\u201d The hosts didn\u2019t object, says Molly, probably because the bill wasn\u2019t a big deal to them. \u201cBut it still shocked me and made me wary of the other guests.\u201d<\/p>\n Email your money conundrums to\u00a0mytwocents@nymag.com<\/a> (and read our submission terms here<\/a>.)<\/p>\n