Dating Horror Stories: Westchester Residents Tell Their Worst and Funniest Tales

One of the biggest reasons so many of us are single is because dating can be downright awful. (Or at least that’s what we tell ourselves on those lonely Saturday nights when we’re watching Netflix.) And we’re not talking about those awkward, can’t-find-something-to-talk-about dates. We’re talking about those dates that make us think it might not be so terrible living the rest of our lives collecting stray cats. We knew we weren’t alone in this misery, so we asked you to give us some of your dating nightmares—all anonymous, of course, to allow everyone to keep grasping that last shred of dignity.   

“After giving my number to a waiter one night at dinner—and a few days of texting—we met at a local bar. I learned a lot of things that night, including the following: First and foremost, that the cells in my town’s prison were small—he was an inmate for a couple months in the correctional facility located only 10 minutes from my house in Valhalla; you are not allowed to flee the scene of a crime—otherwise, you can and will be penalized under the court of law; and Colorado is not exactly an ideal location to sell weed—he moved there for a while, and came back, probably due to his poor profit margin. And if your date asks you if you want to go smoke a blunt at that exact moment (which was roughly 9:15 on a Tuesday night), college tennis is a great excuse to say no.”

“I went to Black Bear in White Plains on a Monday night—watched some football, had some wings, and met this cute guy. We talked, and he asked me to meet up with him on a Friday night at the same place. That Friday, I went back to the bar to meet up with him. He was there at the bar when I got there. We talked, but something was wrong; he kept disappearing and coming back after 15 minutes. So, as I thought it was too weird, after the fourth time, I followed him to the booth area towards the back of the bar. To my surprise, he was on another date! But I ended up meeting one of his friends that night, and we dated for 10 months.”

- Advertisement -

“I once went on a date with a girl, ‘Alice,’ who I met one night at a bar. We had exchanged numbers a few nights earlier, and were sending texts back and forth. We had a great time, had a great dinner, and had a few cocktails. I even got a kiss on the cheek at the end of the night! The next day, I got an email from a guy named Lee, who asked me if I had gone on a date the night prior with Alice—his curiosity ostensibly was so he could ‘finally get away from the relationship and have some closure.’ (I still don’t know how he got my email address.) It turns out he and Alice had broken up just a day before she met me, and the break-up was a bit vitriolic. I met her at a bar the next night, where Lee knew she’d be, and right as I first said hi to her, Lee sucker-punched me in the side of the face and was then booted out of the bar by the bouncers.”

“I had a date with a guy and, not even an hour in, he started to talk about his two nose jobs and how he got arrested when he was 15 for having sex in a Times Square hotel elevator…”

“It was a first date, and the guy was psyched that I am an ‘active’ chick. So he wanted to go for a run, which we did. During the run, he spent most of the time explaining how he is bankrupt. So, the three-mile run concludes, and he asked if I was interested in a bike ride. We head out on the bikes; I let him lead the way. He takes me through wealthy neighborhoods pointing out houses that he did some contracting work on. We come through a neighborhood, flying down a hill as he is pointing for me to look left and right at the houses. Low and behold, there is a speed bump! I hit the speed bump full force, fly over the handlebars, and launch about 15 feet down the road, landing on my arm, shoulder, ribs, and get the wind knocked out of me. It took a moment for him to realize what happened and come back to attempt to help me. He took my bike out of the road first, and left me there! He knew someone in the neighborhood who he asked if they could give us a ride back—after hosing me down in the guy’s front yard because blood was dripping from all angles!”

Our Best of Westchester Party is July 24!

Our Westchester Home Design Awards event is June 26!

Our Wine & Food Festival returns June 4-9!

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Holiday flash sale ... subscribe and save 50%

Limited time offer. New subscribers only.