One of the scariest parts about dating is the unknown – will it turn into a love story, or something more akin to a gross-out comedy? Even if your dating story turns out to be more embarrassing than romantic, at least you have a good story to tell over dinner with your friends, right? This Halloween season, we gathered some of the spookiest first date stories that include ghosts of girlfriends past, a stressful surprise in the closet, and a horrific discovery the next morning, just when you thought the romantic comedy credits were about to roll. Without further ado, here are our favorite scary first date stories shared by our community (and yes, all names have been changed).  

 

A Hair-Raising Discovery from Olivia R. 

 

I met Adam at a mutual friend’s party at the start of the summer, and we made plans to go on a date right away. We met up a few times for drinks and then he eventually asked me back to his place, and we indulged in a passionate make-out sesh the entire train ride home. We had sex that night, which was *actually* great, and afterward, I took him up on his offer to stay over. The only problem? I hadn’t brought pajamas. “Just go into my closet and grab whatever you need,” Adam said to me as he walked toward the kitchen to grab us a late-night snack. I opened his messy closet and started to rummage for a clean pair of boxers and a tee shirt when I noticed a box on the top shelf. Something drew me to that box, and I found myself pulling it off the shelf and peeking inside. There, I found tiny bags of hair, each labeled with a woman’s name. “Oh shit,” I thought to myself, “This guy is a full-blown serial killer.” 

When Adam came back, I couldn’t even pretend that everything was okay, and immediately asked him about the hair. Looking embarrassed, he claimed that it was a joke from undergrad -- all of his female friends had clipped off a lock of their hair and had given it to him. The way he explained it made it sound normal (I swear!), and I stayed the rest of the night, still feeling a bit uneasy. The next morning, I quickly changed, boarded the train, and texted Adam that I just wanted to be friends. I never saw him again, and I have always wondered if Adam clipped a lock of my hair while I was sleeping and added it to his collection… I guess I’ll never know. 

 

The Haunting Ex-Girlfriend by Lyla T. 

 

This is one of those classic New York City love stories...but sadly, I wasn’t the one with the happy ending. I had been texting with Gabe, a guy I met on a dating app, throughout the summer, but we had both been traveling and could never find a time to meet up (this was pre-COVID, btw). Finally, in the early fall, we finally agreed on a time to meet at a wine bar downtown, and the anticipation was killing me. I was fully expecting for us to split a bottle of red, throw on his jacket when it started to get chilly, and take a cab back to his place.. When I got to the wine bar, he looked as handsome as he did in his pictures (rare!) and I was feeling optimistic as he walked me to his outdoor table. But then a pretty sounding voice was calling his name, and it wasn’t mine. We spun around to see a beautiful redhead sitting a few tables away, looking effortlessly beautiful (how dare she), sitting with an uncomfortable-looking friend. It only took a few seconds into the pleasantries for me to realize that they had dated before, and when we finally sat down he told me they had been together, on and off, for three years. “We decided to take a break for the summer,” he told me, sounding distracted, “and I think it was for the best. We’re totally wrong for each other.” That statement perked me up immediately.

Despite his reassurance, I only received a quick kiss that night, right after he walked me home. We texted a bit and I tried to plan a follow-up date, but he said work was getting crazy and he would get back to me. Surprise! He never did. A few months after I stopped texting, and after hours of complaining to my friends over brunch, one of them texted me late one night at a bar in the same neighborhood. “Spotted! Your ghost,” she texted, but it was the woman he was nuzzling that sent a chill down my spine. It was her, the red-headed ex-GF, back for a rekindled romance.

 

A Cursed Stomach by Sadie F. 

 

A few years ago, I had a perfect first date. I was new to the city of Seattle and looking for new friends. If it became romantic, that was okay too! I went on Hinge and met a woman who was also bi-sexual, like myself, and was excited to tell me all about the city and all of the fun things to do. We decided to meet up at a bar that was dark and cozy, and sold these delicious, extremely alcoholic frozen drinks. I hadn’t really eaten all day because I was nervous, but 3 slushy margaritas count as dinner, right? Before I knew it, her hand was on my knee, and we even slipped inside the single-stall bathroom. She massaged my breasts and asked if I wanted to go back to her place, and I immediately said yes.

When we got back to her place we immediately stripped, and she started to go down on me. I felt myself moaning, which was initially from pleasure, and then I realized that no— it's because I need to throw up.

Before I had time to run to the bathroom, I sat up and projectile vomited all over her bed. Yup, all of it. The pillowcases, comforter, and white (ugh) sheets were splattered in my magenta fruity drinks from the bar. The worst part? She didn’t have laundry in her building, so we had to clean everything in her bathtub. I went home, and I’m pretty sure she slept on her own couch (ugh, I’m blushing in horror at the thought). And, yeah—now I typically just stick to beer.

 

A Morning-After Scare: No, Not That One by Maria L. 

 

This happened to me in college, many years ago now, but it still sticks out as one of my most horrifying dating experiences. This was your standard college hook-up: connected at a party, drank sickly sweet mixed drinks, passionately made-out in front of our mutual friends, and wordlessly made our way to my tiny dorm room, where we had sex in my tiny twin bed. The next morning, I woke up feeling excited about the night before. I had always thought this guy was cute when I saw him stroll through the library or dining hall, and he made me laugh all evening. When I rolled to my right side, his back was to me, and I remember smiling while I looked at the freckles on the back of his shoulder. Then...he made a jerking movement. And then another. And another. “Is he having a bad dream?” I naively asked myself as I inch closer to him. Nope, I was the one having the bad dream -- except it was real life, and my hook-up buddy was furiously masturbating into one of my (recently washed) pillowcases. 

“NO!” I screamed, and he yelped in surprise, flipping over and meeting my eyes with sheer horror. After a moment of silence, he quietly got off of the bed, put on his clothes, and left my room, mumbling “sorry” on the way out. My pillowcase was balled up next to me, and to my relief, dry. We never spoke again, but every time I saw him after that I remember us screaming in unison and it made me chuckle (and a little pissed, because I had to buy new pillowcases...for obvious reasons).