Get us in your inbox

Photograph: Lauren Spinelli

New Yorkers share stories of their worst Valentine’s Day

Written by
Rebecca Fontana

Oh, Valentine’s Day. It’s the holiday with the highest stakes for couples—and the high probability that something will go wrong and leave you with a dating horror story you’ll be using as brunch entertainment for years to come. (Can you believe he thought a gym membership would be a good gift?) Whether you have a brand-new relationship status, are a newly engaged lovebird or are just into Netflix and chilling, we want to share your suffering. It can’t be as bad as these eight New Yorkers’ stories…or can it?

RECOMMENDED: Find more Valentine’s Day ideas in NYC

“I was away on business and was sexting my girlfriend on Valentine’s Day. But at the same time, I was also sexting another girl from work who I’d always had sexual chemistry with. She was drunk and texted me, and I was having some kind of SMS threesome. Except that I was also drunk and got confused and sent a text meant for girl No. 2 to my girlfriend. The whole thing blew up in my face, and I broke my girlfriend’s heart. Nothing ever came of the girl from work either. Yeah, I’m an asshole.” 
—Kevin, 39, Hell’s Kitchen 

“My boyfriend wanted to try anal sex for the first time, and since it was Valentine’s Day, I figured, Why not? But we didn’t have any lube, so we ended up using a nearby bottle of water instead, and it was pretty cold and wet, and we were essentially doing it in a puddle on his bed. That was one of my least favorite days. I’m lucky there’s not more permanent damage from that experience.”
—Ariel, 25, Astoria, Queens
“I translated one of [Federico] García Lorca’s love poems for my girlfriend, and she got pissed off and said a real lover would write his own poetry. She ignored me and was really mad. I made a sign on poster board, which I bought at the art store, that read: I LOVE YOU, TAKE ME BACK. I waited outside her office for her to come out, like I was her taxi driver. Eventually, she forgave me.”
—Harry, 28, East Village
“I found out my girlfriend was cheating on me with a dude. So we broke up, but I’d already bought a prix-fixe dinner at a very fancy steak restaurant in Queens. So instead, I brought my straight friend, and the waiter thought we were a couple. He kept nudging us, making suggestive comments about what a great date this was. All the plates had rose petal hearts on them, so it was really romantic. We got super drunk.”
—Becca, 28, Williamsburg, Brooklyn
“I made reservations for my boyfriend and myself to go to a hotel that was doing dinner and a movie. He was supposed to text me when he woke up from his nap and was getting ready, but he never did, and eventually the event was about to start, and I was still at home. I had to call and cancel. He called me an hour later to tell me he overslept. I cried.”
—Elizabeth, 30, Astoria, Queens
“I took my new girlfriend out for a romantic dinner at Bianca, a [now-closed] Italian restaurant on Bleecker Street. The dinner went really well, wine was flowing, and I was feeling on my game. We went back to her place and had sex, which was awesome. Afterward, I went to throw out the condom and found another condom wrapper in the trash. Not my brand. And she lived alone.”
—Dan, 32, Greenpoint, Brooklyn
“This guy at the gym finally asked me out. So Valentine’s Day came, and we had an amazing dinner—it was obvious we were just waiting to get back to his place to rip our clothes off. We started having sex, and after a few minutes he yelled, 'Oh my God!' Yeah, I got my period. All over the place. It was a crime scene. From then on, he thought it would be cute to call me his bloody valentine. It was not cute.”
—Anna, 27, Park Slope, Brooklyn
“One Valentine’s Day I ate Wendy’s, was given conversation hearts as a gift from my boyfriend of a year and lost my virginity. Then two weeks later he broke up with me. That was a real memorable one.”
—Lauren, 20, Financial District

Tweet us your stories and tag then #myworstvday (we promise not to laugh).

Popular on Time Out

    You may also like
    You may also like