As a New York City single, I can attest to the bizarre and heartbreaking milestones one goes through when you’ve lived and dated here long enough. There’s the unfortunately ordinary ghost, the awkward blind date, the messy coworker you once thought you were in love with, and well, I could go one for days. To say the least, it’s hard out there for a New York single. Which is why at our own volition, we decided to host our very first speed dating event, One Night in Two Minutes, at The Hoxton, Williamsburg. We’ve been sharing some of their craziest past dating stories (peep part one here), but first, let us tell you how we got here in the first place.
We figured if we brought some of the cities finest singles together, we could give dating the justice it deserves. And well, some pretty interesting things happened. We had over 300 applicants of all sexual orientations fill out a series of questions, and based on responses, we curated a select group of singles to speed date. The last question asked each applicant to share a snippet of the craziest dates they had ever been on. People told me of their journeys backstage at concerts, of impromptu trips to Japan, and others experienced some pretty wild nights that led until dawn. All signs led us to believe, the craziest nights do happen when they’re unplanned.
I’ll be sharing ten could’ve-been-love stories from our applicants each month. So let’s get going, here’s what happened when some of New York’s most discerning daters shared their most spontaneous dates…
My date asked if I like Elton John. I’m a fan of the classics, so I show up for the date and find out he has front row tickets to Elton John’s sold-out show at MSG. We then proceeded to go backstage and hang with Elton and his crew for the night. The concert was one of the best I’ve ever seen but unfortunately, the relationship didn’t last long…I found out my date was a part of his sex posse in New York. Should have figured something was going on when my date and his friends all took their shoes off during the show and waved them around while Elton was singing to us.
Like, good crazy or bad crazy? Good crazy is pretty low key but awesome. We hit it off and had an amazing night but never got touchy-feely or anything. We’d shut down every place we went to until 2AM and then decided to get a hotel room to “keep talking”. We grabbed a suite at Sixty LES and had the best sex of my life to-date.
Katy Perry’s bassist invited me to a Katy Perry show as our first date. He texted me from the stage the whole time. We officially met afterward when we left to get drinks.
Was in Rome alone and really wanted to see Beyonce and Jay-Z’s On The Run II Tour so I bought two tickets the day of and went on Tinder to find someone to go with me. I put that I had tickets in my bio…it was probably the most matches I’ve ever gotten. Took this cool Italian guy with me and had a blast singing and dancing together. After the show, we went for dinner and then to a party where I met his friends. I’ll never forget it.
A guy I hadn’t seen in ages flew in from California for one night and took me to Hamilton. Original cast. I’ll never forget it.
Storm King on acid. ‘Twas a very aggressive 3rd date.
Flew to Tokyo with a guy I didn’t know to relive scenes from Lost in Translation.
It’s a long story but here’s the somewhat short version…Many years ago I took a girl to a movie premiere in Manhattan and made an excuse to get out of work so I could arrive in time. Although the movie was uninspiring, she was insistent on going to the afterparty. We didn’t know where it was or how to go about it but we’re the spontaneous type so we came up with a plan. We went to the street level and watched the shiny black limos jetting off to the party. Then we found a taxi and offered the driver double fare to follow a limo. When we got to the party, she used her feminine wiles to get us upstairs. We partied till 2 am before heading to yet another party in the Lower East Side that we managed to snag an invite to (a story in itself). From there we were three sheets to the wind but not in the mood to call it a night so we staggered around the LES almost til the break of dawn randomly stopping to dance on street corners. But we still weren’t done. There was a morning dance party going on nearby so we kept things up til almost 9 am. From there, we both had to go to work. It’s the city that doesn’t sleep after all.
Had a very nice dinner date with an older European gentleman who carried a purse. I asked what he kept in there and he said he’d only show me if I showed him what was in mine. His purse contained 6 different vibrators. Mine contained a hatchet a friend insisted I took. Surprisingly he still invited me back to his place…🤪
“Jen” shows up wearing a purple leotard, I’m like “dope”. We go to a vegan restaurant eating mock meat and she proceeds to cry. She then drags me into a whiskey bar and calls me out for not pounding shots. Of course, I’m turned on by all the red flags. On the way back to my place, we stop by a psychic who called us off the street. Jen starts to cry (a recurring theme) at the psychic’s BS. We go back to mine, sleep together and then I kicked her out when I found her rummaging through my shit at 4 am.