He paid for the first date. When she didn’t want a second, he asked for his money back

Samantha Costanza went on a first date with a man she’d met on a dating app in January 2022.

They got to know each other as they both sipped on hot cider because of the cold at the Brooklyn, New York, bar where they’d agreed to meet. When it was time to pay for the drinks, Costanza’s date handed his credit card to the bartender.

A few days later, he messaged that he’d like to see her again. Costanza didn’t feel the same.

“I spent over an hour crafting a very polite reply that assured him I had a lovely time but just did not see a future connection,” said Costanza, 29, a customer operations analyst.

In response, the man asked Costanza if she could Venmo him back payment for her drinks.

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“I was in complete shock,” she said. “It made it seem like the only reason he would offer to pay for my drinks was that he expected something from me.”

Relationship and etiquette experts say the confluence of changing gender norms, popularity of payment apps and the economic climate tightening people’s budgets is making the already fraught first date a little more tense.

One symptom may be more awkwardness around how the tab is handled, in the moment and after the fact. Like Constanza, some women say they’ve had a male date ask for his money back after they explained they didn’t want to go out again.

“We are culturally moving into a dating environment that we’re all unfamiliar in,” said New York-based psychotherapist Carli Blau.

The requests for money back after a disappointing date are a symptom of a much bigger problem with modern dating, said Jon Birger, author of “Date-onomics: How Dating Became a Lopsided Numbers Game.”

These situations would be much less likely to occur on a first date involving two people set up by a mutual friends or a family member, he said.

“It’s a byproduct of the awfulness and toxicity of online dating, where every first date is a blind date with a complete stranger,” Birger said. “There’s zero social accountability, which makes it easier for people to behave badly.”

Dating coach Blaine Anderson said a money request after a date is among the biggest taboos.

“Venmo-requesting a woman to split your first date if she doesn’t agree to a second date is pathetic and unethical,” Anderson said.

When men, in particular, ask for their money back, it can underscore the uncomfortable feeling women can get that their covered dinner came with expectations.

“The man considered the cost of that first date an investment, and that investment did not pan out,” said dating app expert Irina Manta, co-host of the podcast Strangers on the Internet.

Erin, a single 40-something in Pennsylvania who asked to use her first name only, felt unsettled when her date later asked for a refund.

After their first dinner together, she knew she wasn’t going to see him again because of his political views. When their check came, she offered to pay her portion but he insisted on covering the full bill.

But then, the next day, when she explained that she didn’t want to see him again, he asked her to Venmo him $30.

“It really did feel very off-putting,” said Erin. “It really underscores some kind of sense of entitlement on his part.”

Although many find the expectation that men pay for the first tab old-fashioned, others see it as a kind gesture or a way to show interest.

Costanza said she would have been a bit put off if her date hadn’t at least offered to pay.

“Each drink cost $10, so a total of $20 to cover me on a first date seemed like an expected and polite gesture to show his interest,” she said.

On the other hand, it’s important to consider the economy as a backdrop, said New York-based psychotherapist Carli Blau.

Wage stagnation and inflation have left many people feeling squeezed, and dating can be very expensive. Americans spend nearly $700 on dates annually, with the average man spending the most — around $860, according to a 2020 report by LendingTree.

The average cost of a full dinner and a movie across major cities in the U.S. can cost around $159, according to a more recent analysis by MoneyGeek, conducted in 2023.

“That can be really hefty when we’re talking about an economy where people are struggling to pay their rent,” Blau said.

As a result, Blau was a little kinder about the refund requests.

“Is it really that they had a bad intention [or] is it that they really couldn’t afford it?” she said.

If you receive a request from someone after your date, experts say there are pros and cons whether you ignore or pay it.

Ignoring the request sends the message that it was inappropriate, while paying it could be the fastest way to cut ties and never interact again, said Anderson.

Meanwhile, if you intend to Venmo request someone after a date, you may want to reconsider. It’s better to ask to split the bill from the beginning and make your boundaries clear, said psychotherapist Blau.

If getting the money back will help your finances or make you feel better about being rejected, “it’s your right to ask,” she said. 

“It’s also their right to say no,” Blau added.

That’s basically what Costanza did. She ignored the request, and promptly blocked him.

“My time and energy is not refundable,” she said.