Gen Z friendships have entered their nickel-and-diming era

Getty Images; BISome Gen Zers will Venmo-request you for half an avocado.Venmo and Zelle may have made bill-splitting math easier, but they haven't made etiquette clearer.An etiquette expert shared the best way to approach bill-splitting and handle friends who don't pay back.When Joanne Wang went out for dinner to celebrate her 24th birthday, she expected to split the meal evenly. She was spending the evening with a new friend, so she figured they would each pay for their own order. When her friend decided to bring her boyfriend along at the last minute, Joanne didn't think it would complicate the economics of the dinner.Instead, Joanne said, the new friend and the boyfriend ordered oysters and calamari — appetizers Joanne couldn't share because of her shellfish allergy. They also had two more drinks than she had each. At the end of the night, Joanne's new friend put down her card. Imagine Joanne's shock when she received a Venmo request for an even, three-way split. Happy birthday!Joanne, now 26 and an MBA candidate at the Wharton School of the University of Pennsylvania, texted her to explain why she believed it was unfair to split the bill evenly. She said the friend made an excuse about being bad with math and sent her an itemized receipt, leaving Joanne to puzzle out how much to repay her.Bill-splitting has always been awkward. But for Gen Z, which came of age with Zelle, Venmo, and other money transfer apps, it has taken on new dimensions. A 2021 study from LendingTree found that Gen Z was more likely than any other generation to be owed money after lending; a Zelle survey from June found that 76% of Gen Zers said they weren't repaid in full after fronting money for a group trip. Spokespeople for Venmo and Zelle said their apps made it easier for people to repay each other.Payment apps were supposed to make settling up frictionless. They've made it possible to calculate what each person owes down to the drink, shot, or half an avocado (see below) — but haven't solved the question of what we should owe each other, or how to go about it. What should in theory be a pay-it-and-forget-it situation can devolve into ceaseless nickel-and-diming, weeks of pestering your friends to pay you back, and in some cases, the loss of relationships altogether.The cashflow swag-gapJoanne didn't lose her friendship over the bill disagreement, but not everyone is so lucky.Kathryn Yang, a 25-year-old American living in Kobe, Japan, told me that after a few years of splitting rent 50/50, her European roommate suddenly asked to pay less because she was spending most weekends in Tokyo with her partner. The roommate didn't want to stop living in the Kobe apartment; she just wanted to pay less because she was spending less time there."I said yes to paying all the utility bills when she was gone, because I thought it was fair," Kathryn tells me. "What blew my mind was like, if she pays less, that means I pay more, and I couldn't understand why she didn't get how that's selfish."Kathryn and her roommate couldn't come to an agreement, and their living situation devolved into petty fights and passive-aggressive texts. "I called her a bitch and was not nice at all," Kathryn said. They're ending their lease soon, and she hasn't seen the roommate in a month — "So I guess it worked out?"Myka Meier, an etiquette coach specializing in social, dining, and business etiquette, said part of the problem is that, in the payment app era, money is abstract. When there's no actual cash changing hands, you don't see your bank account dwindling. There's no emotional cost to the transaction."Older generations borrowed much more seriously because there was a physical aspect to it," Meier said. "When there's no physical cash exchanging hands, whether it is a $10 debt or a, you know, $500 debt, it just feels less urgent."The price of being preciseMeier thinks a lot of our growing pains around bill splitting and repayment would be eased by having direct conversations about how we expect to pay. "Every group's different, every budget's different, every person's different, but I think if you can discuss ahead, agree, and where possible in writing, it takes that awkwardness away," Meier said.The problem is that not everyone is upfront about their bill-splitting expectations. You might try to divvy up portions precisely, but it can start to feel ridiculous. CashApp's 2024 report on Gen Z's spending habits has a name for this: the Tab Tyrant, or the person who "splits bills with an intense level of nit-picking." My childhood friend Emily Osburn, 24, told me that one of her college roommates requested 25 cents from another roommate who had eaten half an avocado from their communal fridge.The example of the stingy rich friend especially grinds gears. Some people get a bad taste in their mouths when their wealthiest friends insist on splitting single-digit dollar amounts. It's not like you can't afford it, the logic goes.But Meier said that if they're the one th

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