Sex on Friday

10 Terrible New York Dates That Actually Happened

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Everyone has at least one terrible New York date story in their arsenal. And I feel bad for you; I really do. But I don’t feel as bad for you as I do for these poor chumps who went on dates in NYC that are considerably worse than anything you’ve ever experienced.

They were the sweet and hazy first days of a summer fling...

... that could turn into more. I returned to my apartment in Astoria after his friend’s party, where I had noticed his respectable capacity for drink, but didn’t realize just how [boozed up] he was. Following a couple hours of hot-and-heavy fooling around, we fell asleep. I wake up and realize I am in a puddle, for he peed himself not once, but twice in his sleep. We had to dismantle all my bedding and wash each component... it took more than two hours. - K, 28, Astoria

His apartment in Harlem was not only small...

... but he was too poor to afford furniture, so the only pieces he had were a lofted bed and a wooden chair. After our night out partying at Elsa in Alphabet City, I went back to his place for the night. I jumped off his bed to pee and ended up breaking my ankle. He insisted I try getting back up on the bed with my brute arm strength. Since I am not an acrobat, I suggested I sleep sitting up in the chair, mummy-style. He said that was ridiculous so I slept on the wood floor underneath the lofted bed with nothing but a pillow, blanket, and frozen chicken cutlet on my foot. The next morning I dragged myself down eight flights of stairs because -- just my luck -- he also lived in a walk-up. - M, 27, Chelsea

I was encouraged by some staunch advocates of online dating to try JDate

Shockingly I met some of the edgiest, strangest men on this site. First was a man I will call Almond Man because he always brought almonds to feed me on dates since he couldn't afford to go to dinner. Once, after we went for tea, he couldn't afford to pay so we had to walk to the cash machine. But of course, in order to avoid the fee, it had to be his bank so we had to walk all the way from the East to the West Village. That was our first date. For our second date, he decided to cook dinner for me, and he picked me up at my apartment to drive me to his place in the Bronx. On the way, he got a text and suddenly swerved the car in the opposite direction.

"What's going on?" I asked.

"Jumper" he said. It was then I found out he covered the suicide beat for a local newspaper, and he was always on assignment. So our plans for the evening were delayed as he drove me to the gruesome scene of a suicide, from which I was fortunately shielded by hordes of police and firemen as I cowered in his car. When we finally got to his place, he happily showed me the Christmas gifts he'd bought for his kids who were luckily living with their mother, his ex-wife. They were two GI Joe figures. He was proud of himself because he'd dug them out of the neighbor's trash. I knew then there was slim chance of a long-term relationship with a suicide reporter and a dumpster-diving gift giver. - E, 32, Williamsburg

One of the things I found while dating online...

... was a disproportionately high number of agoraphobic men. I met one such agoraphobic individual who never left his apartment in Hudson Heights and required I go to his place for dates while he read passages to me from his extensive Philip Roth selection. On one date, he revealed to me that he had a nasty little habit he was trying to get under control. "I'm a flasher" he told me. "I used to use online dating to meet girls and flash them but they never stuck around. I finally decided I needed a stable relationship."

Of course his idea was that we meet once a week, Tuesday afternoons, at his place for a few hours. That's when I decided I didn't want to be part of his so called "stable" relationship, although I did subsequently develop a nasty little Philip Roth addiction. - B, 36, Williamsburg

I took this girl out for a first date to Bar Six in Chelsea

She was clearly very nervous and had clearly concocted a persona that she probably pulled out on all her dates. She kept calling me "Kid," like she was in a Humphrey Bogart movie. When I wasn’t responding to her very obvious attempts to make out right there at the bar, she told me that I was a typical guy with intimacy issues and that I should figure out my shit before I ask a girl out on a date. - S, 33, Inwood

He had already introduced me to his mom after our first date...

... and his version of rough sex was a little different from mine. Still... I kept going back. The final straw was while we were having sex in his Jersey City apartment, he asked me if I would suck his toes. After I said "absolutely not," he then asked if he could suck my toes. I never saw him again. - E, 28, Financial District

We matched on Tinder. He was a decent looking guy; smart, had an MBA. He kept sending me what I thought were hilarious texts.

I thought it was all deadpan humor. They would be things like, "Just got my night mouth guard so I stop grinding my teeth. I’m 'old man' strong," or "My CEO just walked by as I was talking about shoving meat in my pockets." I thought these were ridiculous ways of engaging me in conversation that were far better than a casual, "Hey." I realized after meeting him that these were not things that were intended as jokes. They were serious observations and disjointed attempts at conversation. I literally misread the whole situation. He wanted to meet at Starbucks for hot chocolate, but I wanted a place that served wine. We met at Ground Central in Midtown. The ordering of the hot chocolate turned out to be a whole complicated thing and face-to-face conversation was like pulling teeth. In fact, we even talked about the dentist. I stayed for an hour. - L, 25, Upper East Side


I found this woman on OkCupid and we really hit it off

She was very cute and our messages to each other sparkled with all the witticisms one can hope for when interacting with a stranger over a dating site. She was also from Israel and I thought that was pretty hot. We decided to meet at Shoolbred’s in the East Village. When she got there we sat down and started to talk. And here was the first problem: I couldn’t understand a single word she said. As we had never had a vocal conversation, it didn’t dawn on me that her accent would be so thickly unintelligible. The few words I could understand sounded like self-deprecation about how painfully socially awkward she is and how she can never get a second date. But I actually have no idea if that’s what she said because I couldn’t understand a freaking thing. I may have made up that entire storyline in my own head because there was nothing else to do. - A, 35, Park Slope

We were out at what NYU students affectionately called "China Wine"...

... a divey Chinese restaurant on the Upper West Side that served free, unlimited boxed white wine with dinner (its real name was Silk Road Palace; they have since closed). My date consumed her boxed Chablis with gusto. We went back to her dorm on Water St and proceeded to hook up. I woke up sometime in the middle of the night to an empty bed. I heard her rustling around in the kitchen and went to see what was up. There she was, sitting on the oven rack, peeing in the oven. "What are you doing?!" I exclaimed. "The bathroom was busy," she slurred. The bathroom was empty. - B, 29, Tribeca

One guy took me to dinner and proceeded to take his shoes off in the restaurant

He called this "Power Play." He then pulled out a weekly pill holder and took all of his meds for something I couldn’t ask about because it was our first date but it may have been serious. He also excused himself, I’m pretty sure, to take a mid-date dump. I say this because he made a joke about it that was likely not a joke. After the restaurant he wanted to walk down by the water. In the fading light we strolled (he limped, given his aching feet in his wingtip shoes) through Rockefeller University. I didn’t even know that place existed, and while I’m sure it was beautiful, it was terrifying in its dim seclusion. When we found a place to sit, a dog passed by and I asked how his dog was. "What dog?" he asked. "The dog in your Tinder photo," I answered. Spoiler alert: he has no dog. I left moments later. Power Play. - S, 25, Midtown East

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Meagan Drillinger is a freelance writer for Thrillist. One of these is about her. Follow her on Facebook, Twitter, and Instagram at @drillinjourneys.