Bartenders Tell Us The Worst Valentine’s Dates They’ve Ever Seen


For some people, Valentine’s Day is filled with heart-shaped candies, stuffed cupid dolls, chocolate, flowers, and an overload of romantic gestures. For others, it’s one of the most dreaded days of the year. While they sit front row for all the stomach-churning PDA, they’re forced to stare down another year of single existence. It can be… aggravating.

There’s a third group in this mix. Those bold souls who embrace their single-ness and celebrate the chance to meet people. That’s who we’re interested in today. The optimistic few who believe that February 14th is the perfect night for a first date. Because that’s a huge risk and deserves a shout out.

Alas — if you’re a member of this bold crew — be aware that bartenders don’t miss anything. They’ve seen your disastrous Valentine’s Day first dates and they told us all about them. Sorry in advance.

The Polyamorous party

Kim Spence, national beverage director at Moxie’s Grill & Bar

“I had a polyamorous table in the restaurant one year, but I think you normally tell the other people involved that it’s polyamorous… needless to say, it ended poorly. Hilarious, but poorly.”

Champagne bath


Brock Schulte, Beverage Director for The Monarch in Kansas City

“I think the worst date I’ve ever seen ended in the woman throwing her glass of champagne in the man’s face after the truth came out about a situation he must have lied about previously. He definitely didn’t see it coming… I should note sparkling wine really stings in your eyes.”

Restroom rendezvous


Morgan Zuch, beverage director for Datz in Tampa, Florida

“Last year we had a couple go to the restroom together and cause a scene with the amount of noise they were making. When the manager went to knock on the door, they stopped and exited a minute or so later. As they left the restroom, disheveled and definitely tipsy, they cursed out the manager on duty with several offensive remarks. We anticipated the ultimate bad yelp review—One Star: “Datz wouldn’t let us bang in their bathroom on Valentines Day!”

Awkward online


Jenn Harvey, bar manager at Temple Bar in Cambridge, Massachusetts

“A couple once came to the bar on Valentine’s Day (they had never met in person, and have only spoken online a few times). The awkward part is, when they sat at the bar, the guy asked the woman if she wanted any food, but she had just eaten. Then he was asking her about drinks and she said she was just drinking club soda. So the guy, not wanting to be rude, or look like a lush or whatever, decided to just have soda water as well. They chatted for 45 minutes or so, and he occasionally checked in with her to see if she had changed her mind about a drink or an app which she kept turning down. There was no check to give them since we served sparkling water complimentary and he was very apologetic to me (which was unnecessary!) and left me some cash as a tip. So, not the craziest story to tell, just clearly not a connection.”

Forced fun


Walker Pickering, bar manager at Crafted at NOSE DIVE, in Greenville, SC

“I don’t think I’ve ever seen a good Valentine’s Day date. I know it sounds cynical but they always seemed forced. (I’m sure the best ones are spent at home.)”

Tinder time


Tainah Soares , bar manager at Area Four Boston

“It was a Tinder date from a regular who would come in at least three to four times a week with a different date. I just felt bad for the girl and maybe felt like I needed to obey to girl code and give her a heads up. I didn’t though — I shut my big mouth and let their evening go on. Needless to say, I never saw her again.”

Financial flub


Eric Tschudi, Sommelier at Shuko in New York

“The worst Valentine’s date we’ve ever seen wasn’t exactly a Valentine’s Day date, per se. A couple who had clearly met via Tinder pulled up to the bar together. After a few minutes of conversation, she asked him ‘So, do you, like, work in finance?’ He did not. Her face immediately turned sour and she just responded ‘Oh’ She proceeded to order a shot of whiskey and left a few minutes later. Not all Tinder dates can be true love, I guess.”

Closing time


Jesse Ostroski, bar manager at Botellón in San Francisco

“I haven’t seen a lot of strange or weird dates, but I have seen a lot of people looking very desperate around closing time. It’s funny how this one certain day can make people lower their standards so much.”

Not a murderer


Jesse Mychal Smith, bartender at Old Major in Denver

“Recently I’ve had the pleasure of watching Tinder dates go wrong. In this episode, a couple that had clearly met on Tinder decided to have their first date at my bar on Valentine’s Day. He was wearing plain but decent clothes and she was dressed to the nines. Then things took a turn: She kept bringing up the fact that the dude she was with could be a psychopath and could murder her (he had given no indication of this). She even went on Tinder while he was still sitting beside her at the bar. She kept telling him he was lucky that she agreed to meet him at all, and she hadn’t thought he’d be this boring. Damn! She ordered about 4 or 5 Long Island Teas and several shots, while he literally just had 2 drinks — she made him pay for everything. My favorite part of this disaster was that he excused himself to go to the bathroom and left through an entrance towards the back of the building. I thought it was money. To be clear, there was only one official entrance and exit. This dude escaped out the back and she went searching for him. Straight up thought he had vanished from the bar.”

Trading up


Tenzin Samdo, bar director at Café ArtScience in Cambridge, Massachusetts

“One girl set up two dates on the same night. The first guy recommended the bar and she met him for one drink. The whole date lasted about 20 minutes. I guess she wasn’t feeling it because she made an excuse to leave. About three hours later, she shows up with a different guy and the first guy was still there. She pretended like she’d never met him and he just kept staring at her, but I honestly don’t know if he realized it was her. I was so nervous, but just shrugged like I didn’t see anything.”