New Yorkers Share Their Freakiest First Date Stories

first date, first impression, nyc dating

New Yorkers Share Their Freakiest First Date Stories

The women of Sex and the City have endured all means of wild and unimaginable first dates, but what do real New Yorkers experience on the daily? According to literally everyone, dating in NYC can be a shitstorm not easily endured by the faint of heart. These first date horror stories, curated by a community on Reddit, are just some of ways New Yorkers have been romantically hazed before finding “the one” in the Big Apple.

Loitering at Penn Station

“He took me to Penn station – no, not a bar in Penn Station. We got two beers at one of those convenience stores and sat in the train station chatting. I thought, ‘Maybe he’s commuter.’ He was not. He lived in Brooklyn, and never commuted out of Penn.”

  • Best Response: I am so sorry. That is horrifying. On the bright side…at least it wasn’t Port Authority?

Do You Even Date, Bro?

“I met a guy who was 40 minutes late to the date, and when he arrived, he was bleeding from a longboard accident in Central Park. We walked the High Line, and at the end of the night, he tried to sell me on a new dating app he created.”

  • Best Response: I’ve showed up to a date with a longboard accident cut. At least I didn’t try to sell a dating app!

Reuse, Reduce, Recycle

“I left a date because the guy told me, unsolicited, that he makes his own towels. Does he weave them? No. He goes down to the garment district every few months to buy a bolt of cotton fabric, cuts off a few feet every week, and uses that as a towel. I asked why. His direct quote, his ‘apartment is too dank and musty for regular towels to dry.’ OK, bye.”

  • Best Response: Did you go on a date with Kramer.

Surprise Photoshoot

“The guy I was on a date with took my photo at dinner without asking and without my knowledge, then posted it immediately on Facebook like I was his girlfriend. That was real fuckin’ weird. I didn’t find out until later, when I discovered that he’d screen-grabbed a photo from my Instagram and used it as his cellphone background. That shit straight up scared me.”

  • Best Response: Really happy to see none of my first dates described so far.

Some Guys Just Can’t Hold Their Hamburgers

“I went out with a guy to a particularly swanky place and he had two martinis. He got so drunk that he took one massive bite of his hamburger and threw it up on the table. It was mostly frustrating, because before he got wasted, there was so much promise. One of those dates where I was having the ‘holy shit, this could be it’ thought. Clearly, I was wrong.”

  • Best Response: This is my favorite story ever.

The End Game

Do you have a weird first date story you want to share with The Rendez? We regularly collect stories to feature on our blog. Get in touch with our concierge, or explore our blog and prep your next first impression.

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