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6 New Yorkers Share Their Most Bizarre Valentine's Day Story

By Gabrielle Pedriani | February 9, 2018 | People

In a city known for being anything but ordinary, it’s no wonder that its residents’ Valentine’s Days follow a similarly eclectic theme. To spice up the traditional holiday tales of windswept romance, we asked a handful of New Yorkers to reminisce on some of the most outrageous encounters they’ve had on the Day of Love. These are their stories.

Brett David, Creative Director Leave Rochelle Out of It

Brett David Leave Rochelle Out of It.

Years ago—I must have been in my late 20s—I went to a Valentine's Day party at a friend's apartment in west Chelsea. He had a huge loft, and there must have been over 200 people there. I had taken a woman I had met recently, and I thought we were hitting it off. That was, until I came back from the bathroom and saw her making out with a man who was considerably better looking than I was. Defeated, I went to grab my suit jacket off the chair I had been sitting at, only to not find my Prada suit jacket, nor the $1,800 in cash I had in the breast pocket for my rent that month (I had just gotten paid). I was beyond furious. I walked out, took the train back uptown, and went home, only to realize that my house keys were in said jacket, too. I scaled the fence to my backyard, ripped my pants, and wound up needing three stitches in my hand that next morning from the barbed wire.

Iris Smyles, Author of Novels Iris Has Free Time and Dating Tips for the Unemployed

Iris Smyles.

When I was about 20, my boyfriend at the time came over with a small heart-shaped box of chocolates he’d gotten from the drugstore. He was in tears. He really wanted the large one, he said—had always dreamed of getting one of the large ones, but he couldn’t afford it. Would I go back to the store and buy it for him? I did, and after I finished mine, he wouldn’t share any of his with me.

Nana Wereko-Brobby, Founder of Social Concierge

Nana valentine's day story name.

The date that really took the biscuit was with a charming entrepreneur I met about six years ago.

On the night of the date, he had a martini ready for me when I arrived and proceeded on the charm offensive. He suggested we move on to another Mayfair hotel bar and then piggybacked me through London to the river. As he kissed me on the steps of a church, I was smitten. And the next move was to our final destination, a stunning hotel where he'd booked a room—brashly declaring it was on him—and quickly swooping me upstairs to the mini bar (and bed).

The next morning, we watched TV shows together, chatted, and had a parting kiss. As I walked to the station 10 minutes after leaving him I received this text:

"Wonderful evening. Would you mind transferring £250 to my account for your share of the hotel? Consider it a donation to Help the Sex Heroes Foundation (smiley face)”

Dumbfounded, I wired him the funds and deleted him on Facebook.

Gabrielle Edwards, Co-Founder and Head Buyer of Mixology Clothing Company

Gabrielle Edward.

A few years ago I was dating this guy, and it was getting kind of serious. He had an allergy to most liquor and would only drink vodka made from potatoes. I called my best friend to ask where I could find this specific kind of vodka, and she gave me a place. She always knows where to go for these kinds of things. So we go out, have a great time, and I call my friend to tell her about the date. She replies… “I know.” I said, “What do you mean ‘you know’”? She said, “I was around the corner when you called me, so I decided to eavesdrop on you. I sat right behind you at the bar and listened to your whole date.” Of course I didn’t believe her, but then she literally, word for word, told me everything we spoke about on the date. We still laugh about it until this day.

Monica Piper, Writer and star of Not That Jewish

Monica Piper.

I was working a special Valentine’s show at a comedy club in Sacramento. All the couples were given champagne and little cupid hats to wear. I did a joke. Big laugh. A drunk man in front shouts, “That’s not funny!” His date screams, “Yes it was! Be quiet!” “Don’t tell me to be quiet!” The audience shouts: “Be quiet!” He now starts heckling the audience. His date shouts, “I had no idea you were such an a—hole!” The audience cheers. He tells her, “We’re through!” “Fine with me!” They stormed out of the club. And that’s how one of my jokes caused a couple in silly hats to break up on Valentine’s Day.

Josh Beckerman, The Foodie Magician

Foodie Magician.

I was on a V-Day date four years ago at Carbone with a gal and I was pretty drunk. I saw Jay-Z and Jake Gyllenhaal in the corner having a dinner with friends. I went over and started doing magic to them. Jay-Z then called my date over and started asking her questions like, “What number date is this?” He guessed “second date.” She told him we were “just friends.” I went home alone that night. #stillsingle

Photography by: Photograph by Carol Rosegg (Piper)