Get us in your inbox


10 of the worst New York City dating horror stories

Written by
Jillian Anthony

We collected some of our favorite dating horror stories from New Yorkers, and man, after reading these, our bad dates aren't sounding so rough. Have your own awful story to share? Submit it; we need to hear! 

“I was hooking up at my house with a girl I was seeing, and she was in the middle of giving me head. All of a sudden, she stopped and ran into the bathroom. She comes out five minutes later with a horrified look on her face and her hand over her mouth. She had lockjaw and couldn’t talk. I asked, ‘ER?’ and she nodded, so I drove to one near her place. I asked if she wanted me to stay with her, but she shook her head no. I got a text around 6am that she was home, but we never spoke again.”
—Joe, Soho

“I met a guy on Tinder. When we met for drinks he showed up hammered—like Anna Nicole Smith at the Billboard Awards wasted. Being the shining star of decision making that I am, I went home with him. After about five minutes of vanilla sex, I noticed he wasn’t really into it anymore, because he had fallen asleep on top of/inside of me. Mortified by the experience, I got the hell out of there. I woke up the next morning to a text from him that read, ‘LOL you leave?’”
—Lorelei, Cobble Hill

"I went on a first date with a really cute girl, and we ended up getting pretty drunk and making out. Our second date was going similarly, so I asked her to go home with me. We kissed for a while in my bed, then passed out. Around 3am, I woke up to the sound of water running. I looked up, and she was squatting beside my bed, peeing. I yelled her name, and she seemed to kind of wake up, and she just apologized, got her stuff and left. Then I cleaned up her mess."
—Derek, Bushwick

“I was hooking up with a guy for the first time, and when his shirt came off, I saw his nipple was pierced with two large balls on either end. I loved it, so I started playing around and biting it. Everything was going great, until I bit down a little too hard and immediately felt a searing pain. I had chipped off a huge piece of my tooth. After an emergency trip to the dentist, we decided not to see each other again.”
—Daria, Soho

“Back in college, I went on a first date with a guy I didn’t know well. He told me that before dinner we had to ‘stop for cash.’ He took me to a blood bank, where we both donated blood for $10 each. I was so shocked and naive that I just sat there and did it. I still went to dinner with him afterward—I was young, okay!”
—Mara, Lower East Side

“I was on a Tinder date with a really cute guy. We shared some food, then went to a local dive bar and started doing shots. Soon I was watching him fall apart in front of my eyes. He started telling me about his recent breakup, then began crying right in front of the bartender. I said I’d walk him to his house nearby, and he threw up on the way there. I don’t think he’s quite ready to date.”
—Anna, Chelsea

“I’d just had a couple of drinks with a girl on a first date, and we were wandering around the neighborhood. She suggested we stop into Pommes Frites and pick up some french fries for a snack, and I laughed and said, ‘Sorry to tell you this, but I hate french fries.’ She stopped dead in her tracks, looked at me for a long while and said, ‘I’m sorry, I can’t do this,’ before walking away. I am baffled by her reaction to this day.”
—Tommy, Lower East Side

“I had a nice date with a guy who seemed normal. He texted me right after we parted ways, and I thought I’d respond when I got home. But by the time I arrived an hour later, he had texted a few more times, which kind of creeped me out. By the time I woke up the next morning, I had 12 missed calls, three voice mails and many, many more angry texts calling me an ungrateful bitch. I definitely dodged a bullet there.”
—Tanya, Midtown East

“I once went home from the bar with this guy I barely knew. He had awful tattoos—one was a sun around his belly button, another was a clown fish with an actual clown face—but he had a great body. The next day, we took a cab together downtown. Our driver was speaking Arabic on the phone, and the guy started making bigoted remarks, loudly, then got out and said, ‘No tip for foreigners like you.’ I had no idea I’d slept with a racist!”
—Jennifer, Williamsburg

“An old friend set me up with this girl who looked cute in her pictures, but when I showed up, she looked much older. The waitress asked for our drink order, and my date said, ‘I don’t put that poison in my body.’ Okay. Then the waitress asked us what we’d like to eat, and my date said, ‘I’m vegan and can’t eat anything on this menu.’ She picked the restaurant!  I tried to ask her about herself, but she just gave me one-word answers until I finally said, ‘You can leave if you want.’ She got up and left without saying bye.”
—Artie, Chinatown

Popular on Time Out

    Latest news

      Read next