Ask A Bartender: The Worst (and Best) Valentine's Day Dates You've Seen

Ask a Bartender

You ask, they answer.

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Kris Doyle of Trattoria Neapolis in Pasadena, CA

Ever had a terrible Valentine's Day date? We bet that these bartenders have seen worse. As one of those holidays that prompts high expectations, V-Day is full of potential disaster. We asked bartenders about memorable Valentine's dates they've witnessed from behind the bar. Here's what they had to say.

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Thomas Gebbia of Thistle Hill Tavern in Brooklyn

"One very sad February 14th, a very good-looking couple sat at my bar for dinner. I noticed the man was rather jumpy and sweaty. At the end of the meal he stood up and asked for the room's attention. He got on one knee, pulled out a small box, professed his love and asked the woman to marry him. 'NO,' she said. 'I know you've been cheating on me.' Didn't see that one coming." — Thomas Gebbia (Thistle Hill Tavern)

"Valentine's Day is the one night of the year where people are so focused on themselves/each other that you might as well be invisible—which is fun in its own way. One year a poor group of four single ladies out for some 'anti-Valentine's' got into a screaming match (one girl threw a shoe!) and had to be escorted out. I hope they made up on February 15th." — Lauren Lathrop Williams (Jsix Restaurant)

"At a previous bar I worked at, I witnessed a guy who was clearly using an online dating service come in on multiple dates with different women. One of which was one Valentine's Day. He'd always get there first, put down two drinks before the woman arrived, and then he'd sip a glass of water when she showed up. He usually struck out." — Dan Rook (South Water Kitchen)

"I've witnessed a Valentine's Day blind date before and it's so obvious because the person who arrives first is scouting the room the whole time. Then there's a sign of relief or disappointment when the second person arrives." — Ergys Dizdari (Filini Bar and Restaurant)


Jim Kearns at PLAY in NYC

"I did have one miserable couple at my bar, years ago at Freemans, who were mad that I was making noise and moving things while I was setting up for a heavily booked dinner service. The woman picked up my garnish containers and started banging them on the bar and moving them, to try to prove a point. I would imagine theirs was not the happiest of Valentine's Days." — Jim Kearns (PLAY)

"Let's get this straight: don't bring your date to a bar for Valentine's Day. You should end up at a bar after your real date. When I see you at midnight, your date better be over or just getting started." — Dan Bronson (The Strand Smokehouse & Crescent & Vine)

"We actually just a had a couple get engaged here at FishTag. It wasn't on Valentine's Day, but they had their first date here on the holiday last year and they wanted to come back to pop the question. They even sat at the same table that they had on their first date." — Gianni Cionchi (FishTag)

"My favorite is single ladies that get wild with their girlfriends in protest of not having a Valentine." — Jen Queen (Saltbox Dining & Drinking)

"I've witnessed a lot of different scenarios on Valentine's, from first dates to long-lasting love and passionate hookups. My favorite moments are watching the older couples who break out one of their cellared bottles of wine for the special night, and hopefully they will let you in on a taste!" — Ryan Prevost (Kabocha)

"Once a man proposed to a young lady and she did not accept, so I created a cocktail called 'Crash and Burn' for his epic disaster; it's one of my all-time favorites! It's a fairly simple, straightforward recipe: 2.5 ounces of tequila, neat, and REPEAT!" — Pablo "Papi" Hurtado (The Rittenhouse)

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