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The 7 Cringiest Things You Can Do On A Date, According To Bartenders

Yes, they can tell if you're on a first date from behind the bar.

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First dates are rarely perfect. Whether you’ve been on Hinge forever or recently re-entered the singles pool, meeting up with someone you don’t know can feel inherently awkward — and a lot more can go wrong than spilling a drink on your companion or calling them by the wrong name. And few have a better front-row seat to all the cringeworthy moments than bartenders: They can pinpoint the exact moment when a meetup is about to go from bad to worse, whether it involves people drinking too much or bringing up hot-button topics before the second round’s been ordered. Ahead, seven barkeeps on the biggest mistakes they’ve seen people make on dates.

Ordering For The Other Person

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Ordering a drink for someone you don’t know very well has “disaster” written all over it, especially on a first date. Just ask Richmond, Virginia-based bartender and TikToker Katie Stuart, who has witnessed the cringey habit firsthand.

“I had one time where this guy kept ordering for the other person, his date, and she got mad. Before I said ‘Hi, my name is...,’ he’s like, ‘I’m going to get blah, blah, blah, she’s going to get this, and can we get two waters?’ I looked at the date, and I was like, ‘Hi, I’m Katie. What’s your name?’ And she told me her name and that she didn’t want wine. She wanted a beer because we’re a beer place.”

Ordering a second or third drink for the other person after they’ve already expressed they’ve had enough is a pretty undesirable practice, too. Trevor Easton Langer, head bartender at Jac’s on Bond in New York City, considers this to be one of his “bartender red flags.” “I always side with [the] person who says they don’t want another,” says the expert. “It’s a manipulative and gross power dynamic to essentially force another drink on someone just because you want another or since it’s on you.”

Flaunting Money To Impress Your Date

Talking about how much money you have isn’t as attractive as you might think it is. In fact, New Jersey-based bartender Jeff Umana shares that he’s seen dates ruined by someone trying to show off how much money they have or how they used to pay for things for their ex. According to Umana, using money as a social crutch really becomes an issue when one party orders an expensive drink and the other doesn’t. “When one of them orders a top-shelf whiskey and the other orders a Tito’s club, and Mr. Top Shelf says something like, ‘Oh, I used to drink that in college…’ and there goes the date,” he says.

Having A Go-To First Date Spot

You might think it’s convenient to have a consistent first date location, but bartenders say it can get you in trouble down the line, especially if your fellow barflies don’t know how to keep a secret. Michelle Kimball, a bartender in Charlotte, North Carolina, recalls an instance when one regular informed another of his first date plans, only for them to run into each other the next night… while the regular was out with someone else.

“The [second] regular was like, ‘Oh, my God. How was your date yesterday? Wasn’t it your first date with that girl?’” Kimball says the guy on the date tried to play it off, assuring the other regular that he was currently on the date she was referring to, but there’s no coming back from that.

Stuart points out that you also run the risk of running into your past flings (or even ongoing situationships) this way, which almost always leads to one party asking “Do you just bring all your dates here?”

Addressing Sensitive Topics

Several bartenders say it’s best to steer clear of any sensitive topics, like religion or politics, the first time you see someone — classic advice, sure, but they’ve seen the consequences firsthand. “If you don’t agree, and that gets brought up… you can just tell that there’s not going to be a second date,” Kimball says. If those subjects are deal-breakers for you, there are filters you can apply to your dating app profile to ensure you align on those topics before you even pencil in a meetup.

Abbey Fickley, a bartender in Pittsburgh, says she’s seen dates devolve into screaming matches, adding that it almost always starts with a smaller argument about differing beliefs before escalating into something bigger. Once, a date got so bad the staff had to physically separate the couple. “We literally had to put one in one room and one in the other until their Ubers got there,” says Fickley.

Similarly, SoCal bartender Sally Chan recommends refraining from oversharing on a first date, whether that means disclosing how much you make or committing the ultimate no-no: talking about your ex. “It’s not a good look on [you] for sure,” she says.

Drinking Too Much

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It might seem obvious, but be sure to know your limits before arriving at your date. Still, first date nerves are a very real thing, and according to the bartenders, sometimes they lead to people getting too drunk when meeting someone new. Stuart says a regular once came in a half-hour early and asked for shots before his date had even walked in.

“Four shots later, his date arrives, and he is obliterated… And then he asked for another shot. I said, ‘You’re five shots deep and your date just got here. Are you going to even remember who she is?’ in front of both of them,” Stuart says. It’s always important to know your limits — especially when going out with someone — not only to ensure your safety but to prevent yourself from committing other first-date faux pas that might happen if you loosen up a little too much.

Hitting On Other People

No matter how badly your date is going, don’t hit on other people while you’re with someone — including the bar staff. Chan shares a story about a customer who would always come in with a different woman and repeatedly flirt with the bartenders, calling them “mi amor” presumably behind his dates’ backs. Consider this your reminder to turn off the first-date flirting when talking to the bar staff, folks.

Being Awkward About The Tab

Deciding who’s covering the tab already isn’t fun to begin with, but nothing kills the vibe more than being forced to pay the bill unexpectedly. Umana once witnessed a cringey date that involved one party being cut off because he got too drunk and was acting obnoxiously toward his partner. When the night was over, his card was declined. Ultimately, his date had to pay for his drinks — and his ride home. That’s strike one, two, and three, all in one go.

These may be an extreme scenario, but there’s no denying that paying the bill is one of the most uncomfortable parts of a date. To avoid the whole song and dance, Fickley recommends getting to the bar first and starting a tab beforehand so there’s no debate about who should pay. Plus, if you cover it on the first date, it gives you an excuse to plan the second date. “Tell your crush they can pay next time [if all goes well],” says Misha Chavez, a bartender at Lullaby in New York City.


Katie Stuart, bartender and TikTok creator

Trevor Easton Langer, head bartender at Jac’s on Bond in New York City

Jeff Umana, bartender at Village Hall in South Orange, New Jersey

Sally Chan, bartender and TikTok creator

Michelle Kimball, bartender and TikTok creator

Abbey Fickley, bartender and TikTok creator

Misha Chavez, bartender at Lullaby in New York City

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