Why ’tipflation’ might ruin your chances for a second date

Last summer, Sherry Gui brought a date to her local bar in Manhattan. Gui, a law school student, had been going to the establishment for three years, and was friends with the bartenders and staff. When the evening ended, the guy picked up the check, which she was grateful for — until he wrote in the tip amount.

“It was lower than what I normally would [tip] and actually lower than the expectation I had of him, like he has a respectable job,” said Gui, 29. “I just felt like it was a representation of me, as well.”

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Early dating can put a magnifying glass to the differences between two people. One of those areas may be tipping practices, made only more fraught of late with the ubiquity of gratuity screens and changing expectations of when we should tip and how much. 

“It could be a deal breaker on a first date,” said Lizzie Post, co-host of the Awesome Etiquette podcast, about someone’s tipping practices. You or your date may conclude, Post said, “‘I’m not even going to give them a second chance.'” 

The main question in most people’s minds during the first few dates is often: Do I want to keep seeing this person? And so it makes sense that single people are taking everything into consideration about the person across from them at the table.

Their tipping behavior might be especially revealing, said Irina Manta, a New York-based dating coach and consultant. 

“I do think that someone who does not tip properly is probably going to correlate with other types of generosity,” said Manta, who also co-hosts Strangers on the Internet, a podcast series about online dating.

Simply put, not leaving a good tip — or any tip — can be a huge turn off, Manta added. 

Blaine Anderson, a dating coach for men in Austin, Texas, agreed: Tipping “is important because it can be a proxy for how you treat everyone in your life.”

But if you’re confused about how much to tip and when on a date, you’re not alone. 

During the fourth quarter of 2022, the frequency of tips provided at full-service restaurants grew 17% while tip frequency at quick-service restaurants — like coffee shops — swelled 16%, according to a study from payment processor company Square. 

It can get tense if waitstaff presents you with bigger tip percentages than they used to, or your barista flips the screen with tip options, when you’re with someone you’re trying to impress.

Keep in mind that some traditions remain in place, said Nick Leighton, the co-host of the etiquette podcast Were You Raised by Wolves?

“While the number of iPads asking us to tip 25%, 35% or 45% for a cup of coffee may be growing, the etiquette rules around tipping haven’t actually changed,” Leighton said.

Leaving a 20% tip at restaurants is still the standard, experts say. “You want to at least make sure you’re doing the minimum when it comes to tipping,” Post said. 

For pick-up food and drink options, there is more discretion. These situations should make you think back to the tip jar days, Post said: “You often leave a dollar or two per drink, depending on how complex the drink is.”

Meanwhile, you always want to have a range of bills handy for moments where cash tips are appropriate, Anderson said: “Being prepared with cash for these situations makes you look smooth.”

Manta, the New York dating coach, said it was bad form to be too nosy about your date’s tipping practices. When she was dating, she wouldn’t lean over to the other side of the table to get a look at the check. 

“It’s not like I played Sherlock Holmes to find out how they tipped,” Manta said.

While being a generous tipper can impress your date — and more importantly, fulfil your responsibility to the people serving you — you don’t want to be a show off, experts say.

“Definitely don’t call attention to your tip, no matter how generous it is,” Anderson said.

You want your tipping to be “a gracious moment,” Post said.

“If you flash your money to try to get better service, or if you’re really showy, it does just come off a little tasteless,” Post said. “People feel the show of that and it doesn’t always feel comfortable.”

You also don’t want to tip any differently on a date than you normally would, Leighton said: “If you never actually tip, that’s something your date should know about you and you shouldn’t pretend otherwise.”

In 2017, Manta matched with Carlos Farini on the dating app Bumble.

They had a few glasses of wine at bar on their first date. As a former service worker himself, Farini always tipped well, which reflected the number-one quality she searched for in a partner — kindness.

They’ve now been happily married for five years.