Updated: January 26, 2023
We asked New Yorkers to tell us the absolute worst date they’ve ever been on. Here are the best (worst) responses:
The possible thief:
We went to a Nets game, and at halftime I went to get us more beers. When I came back, he had completely left Barclays and all my stuff was missing. I promptly returned to his hotel in Midtown to try to get my stuff, but the hotel staff couldn’t get in touch with him. I’m informed that the best thing to do is to call the cops. So, I do. I report my date for stealing my property and ask them to come to the hotel and get my stuff back. Meanwhile, he waltzes into the lobby carrying McDonald’s acting like he didn’t know who I was or that he had just left me in Brooklyn.
The armed robber:
I met a guy at a bar one night who seemed cool; we flirted for a bit and exchanged numbers. I went on a date with him a week later and found out he was on parole for attempted robbery (which I eventually remembered hearing about on the news). He had no problem telling me about the incident in detail and even had the nerve to act like he wasn’t in the wrong.
I’m a native New Yorker and a teacher; he was from Florida and an accountant. He spent the entire dinner explaining how the NYC public school system (the same system I had spent 13 years of my life in as a student and several years as a teacher) works and what the problems with it are. The waitress didn’t even offer us a dessert menu. I think she could sense how much I wanted to get out of there.
The possible murderer:
I went on a first date with a guy who wanted to do something unusual, so he took me to Roosevelt Island in the dead of winter to explore. There was no one around as it was so cold. During our frigid walk, he stopped and stared at the river, then asked, “I wonder how many dead bodies a year wash up here?” I legit thought I was on a date with a murderer. He repeatedly texted me after that date to say what a wonderful time he had and how he wanted to go out again. Hard pass!
The lubricant deceiver:
My parents came into the city and this guy I had gone on a few dates with messaged me the same day to see if I wanted to hang out. I responded with, “Oh shoot! I’m sorry! I actually have plans today, but maybe another time?” He responded with the following: “You know, I really don’t appreciate this. I am looking for someone serious and if you’re fucking around with multiple guys, I really think we should just end this now! I fucking hate women who play games!” I replied, “I’m hanging out with my parents…” It took him two hours to apologize, but by that time I was done. I told him it was nice meeting him, but I didn’t think it was going to work out. A month later he randomly messaged me a picture of his newest tattoo: a camel on his toe. I did not respond.
The “whacky” guy:
We had a good time, he was super silly, and had a whacky energy…turns out he was tripping balls on mushrooms.
I went on a date with someone I matched with on the League. He showed up 20 minutes late and said that he’d just come from the office, but I could tell he had already had a few drinks. He kept me there a long time and drank a ton of vodka sodas with Grey Goose, which he specifically asked for. At 11 p.m. I was ready to go home, but he suggested we go to one more bar. I declined and when we got the bill, which was outrageously expensive because of all of his top-shelf vodkas, he said he’d left his wallet at the office. But he said it in a way that I just knew he’d known this the whole time. (He also took a yellow cab to the date, which I saw him get out of, and paid for it somehow?!) I was pissed and tired by this point, so I agreed to pay the bill with the expectation that he’d Venmo me like he promised he would. He was still bitter about me not wanting to go to another bar (but excuse me, why would I agree to that knowing I’d have to foot the whole bill?!), so we ended the date on a bad note. While in the cab home he Venmoed me $5 “for the drinks.” The bill was almost $150! He definitely saw the bill, as well, so he knew how much it was. I blocked him on everything after that. I’m not one to believe that men should pick up the tab on every date, but that was just BEYOND.
I went out with a guy I met through friends who was an engineer. Over dinner, he consistently told me that he didn’t think many women are engineers because “they are social creatures and are better at being schoolteachers and nurses.” When I told him that he was being offensive and ignorant, he said that I was attacking him and didn’t want to talk about it anymore. He still tried to kiss me and take me home.
The deli dater:
There was this guy who I met on Tinder and had been on a couple of dates with. On our third date, he invited me out to a show. I was really excited because I was actually pretty into him. Once we were at the venue, he casually mentioned that a friend of his was going to meet up with us; I didn’t think much of it. Well, I met his “friend” and she seemed nice enough, but pretty uncomfortable. When he went to the bathroom, I tried to make small talk and asked, “So how do you know _____?” She said, “I don’t.” It turned out that he had just found her on Tinder and invited her to OUR date! When we confronted him about it, he said that he was hoping for a threesome. He literally thought that if he got two bi girls in the same room, he could trick us into a threesome! The girl and I ended up leaving and getting drinks together without him.
The cop evader:
On a date with a guy in Central Park, we saw police officers and he said we should avoid them. I wasn’t sure why he wanted to avoid the police, but I knew it was a red flag. He said he was really concerned about a sign there that said “Icy conditions,” even though all the ice had melted.
I met a guy at NYCCT [New York City College of Technology] who was the same year as me. We had been dating for about three years when he told me that he has a kid who is 15 years older than me, that he has a front set of dentures, and that he’s recently separated.
And finally, the…whatever this is:
My favorite is the guy who blacked out mid-date, forgot who I was, ran away from me when I tried to help him into a cab, and then called me an hour later to accuse me of stealing his money.
Some responses have been edited for length and/or clarity.
What’s the worst date you’ve ever been on? Tell us in the comments!