
“In 2025, PayPal released a survey that showed 32% of Gen Z respondents have either received or sent a payment request for the entirety of a bad date’s costs, while a 2019 Venmo study found that 66% of participants agreed that inviting someone out and then sending a surprise bill is unacceptable date behavior.” — Bustle
Ijust stumbled upon a piece in Bustle about what the author calls the “rise of the revenge payment request,” and I have to admit, I was surprised.
The article describes people who have gone on a bad date, decided they weren’t interested in seeing the person again, and then sent the other person a payment request afterward to recoup some or all of the cost of the date. In one example, a man who had paid for a date later sent the woman a request for half the bill because he felt the date had gone badly.
My first reaction was: Really?
I have a daughter in her early 20s, and she tells me about her dates, so I find these kinds of stories particularly interesting.
The way she describes dating, the guys she goes out with typically pay for the first couple of dates. Then she pays for the next couple. Once they know each other better, they generally alternate paying. The dates aren’t extravagant, either.
And if a date doesn’t go well? Neither person expects a refund.
Her friends often take a different approach. Many of them simply split the bill when they go on dates, which means there is no question afterward about who owes whom money.
I can understand wanting to split expenses if that’s what both people prefer. What surprises me is the idea of agreeing to pay for a date and then, after deciding it wasn’t worth pursuing, sending the other person a bill.
Dating doesn’t come with a money-back guarantee. Sometimes you have a wonderful evening and never see the person again. Sometimes you realize within an hour that there is absolutely no chemistry. Isn’t that simply part of dating?
When you agree to go on a date, don’t you also accept that it may not work out? You might spend money on dinner, drinks or coffee and discover there is no chemistry. That is simply part of dating. If you’re so concerned about spending money on a date that you need to recover the cost when things don’t work out, perhaps splitting the bill from the beginning makes more sense.
There is nothing wrong with being careful with your money; what seems odd is willingly paying for a date and then deciding afterward that the other person owes you a refund because you didn’t enjoy the experience.
That’s why I can understand the approach some younger daters take and simply split the bill from the beginning. It eliminates some of the awkwardness and expectations surrounding who paid.
Dating is about taking a chance on another person. Sometimes it works out, and sometimes it doesn’t. You may spend a little money along the way, but isn’t that part of the dating experience?
Would you ever ask someone to reimburse you after a bad date?
Do you think the person who invited someone out should pay, regardless of how the date turns out? Or is splitting the bill the better approach, especially when you’re just getting to know someone?
Here is the article if you are interested in reading it.
Ew, You Sent Your Date A Payment Request?
We’ve entered a new era of romance in which virtual payment requests aren’t just about splitting the bill — they’re…
www.bustle.com
B.R. Shenoy is a lifestyle writer and the owner/editor of The Family Desk on Medium. She also publishes Musings and Reflections, a newsletter on Substack, and is the coauthor of The Invisible Lines of Poverty.
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This post was previously published on medium.com.
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