“I Hooked Up With The Wrong Roommate” & Other Halloween Hookup Horror Stories

Halloween is the one time of year when your costume might be hotter than your one-night stand, your hookup might be scarier than the haunted house down the street, and your pride is probably abandoned somewhere on the sticky floor of a frat basement. From parking-lot quickies to regrettable dorm-room flings, Gen Z has officially made Halloweekend the Super Bowl of questionable hookups. So, we asked seven students to spill their spiciest, scariest, and most unhinged Halloween hookup stories — equal parts tricks and treats.

What’s fun about Halloweekend is the built-in excuse for chaos. Everyone’s drunk on some liquid courage (and maybe lukewarm jungle juice leftover in your Halloween borg), half-naked in the name of “costume creativity,” and just spooky enough to blame blackout decisions on the moon. Forget haunted houses. Nothing’s more terrifying than bad breath, puke breaks in communal bathrooms, whiskey dick, making out with someone only to realize you actually wanted their roommate, or finding out your sneaky link has been hiding… a MAGA hat. (Chills.)

So, light your new TJ’s pumpkin candle and get cozy, because whether you’re slipping into fairy wings, channeling your inner slutty nurse, or rocking your favorite pop-star alter ego, Halloween is creeping up fast. And if you end up with a ghost (aka no texts back), a goblin (aka the situationship you regret), or something surprisingly magical, one thing’s certain: Halloween hookups write themselves, and these seven stories are hauntingly entertaining.

All names have been changed for privacy. Responses have been edited for clarity and length.

Ella, 22: “Before I knew it, I was running to the bathroom.”

“So one night during Halloweekend, I was dressed as a fairy when I met this guy at a party. I was pretty drunk, and before I knew it, we were in my dorm room. We started hooking up — as I was wearing ear cuffs and a fairy dress — when everything started spinning. I was pretty drunk and told him I needed a minute. I felt like throwing up, and he opened the communal bathroom door and asked if I was OK, and I said I just needed a minute, and he left. Right after he left, though, I instantly felt better — basically a sign from the universe that we weren’t meant to hook up.”

Julia, 22: “I literally texted him, ‘I have a riddle for you. Come see me.’”

“I take Halloween really seriously, almost like my birthday. Every Halloween since my senior year of high school, I dress up as somebody who has red hair because I’m a redhead. But, throwing it back to when I finally had my first boyfriend as a college freshman, I dressed up as the Riddler from Batman. I texted him because we had plans for Halloween that night, and I was trying to be sexy — sending him funny riddles and stuff. It worked for the night, but then he broke up with me the next day.”

Grant, 22: “I was flirting with this guy at a party, but I ended up going back to his dorm with his roommate.”

“Freshman year, I started making out with this one guy, and while we kissed for a little bit, his breath was terrible. I fled when I could, hid out in the gender-neutral bathroom, and texted the first guy I’d actually wanted from the party. When his roommate finally left, I went back to his room and confessed, ‘I regret my decision. I hooked up with the wrong roommate.’ He laughed, pinned me down, and, well… we slept together.”

Taylor, 22: “He didn’t even drive me back.”

“During sophomore year, I was talking to this guy on Tinder. He was five years older than me, and he was in town for the night from out of state. It was Halloween night, and I had a cross-country meet the next morning, so I wanted to go to bed early. But, at the same time, this dude and I were messaging, and we ended up meeting up after a Halloween party. The only problem was that I was living with three other people at the time, but he was like, ‘I’ll have sex with you anywhere.’ Naturally, I was okay with that, and we ended up going to a parking lot across the street from my dorm. So, he’s on top of me, and we’re making out. But then we realize that there’s a car with headlights on, and we think we’re being watched. Basically naked, we drive to another level of the lot and continue to have sex in his backseat. He came pretty quickly, and then I literally walked back to my dorm. I never saw him again.”

Maria, 22: “I stood outside his apartment in my costume in the cold.”

“It was the week before Halloween, and I was at a house show with some friends. I had been seeing this guy for about a month, and he offered to pay for an Uber to his apartment after I finished up at the party. I ended up staying an hour or two later than planned, but I texted him saying that I would be there soon. After no response, I drunkenly walked about 25 minutes to his apartment and called him about 18 times in the process. After waiting a little bit, the door finally opened, and it was his roommate, whom I’d met a handful of times, leaving to go get Zyns from the convenience store. ‘Is so-and-so there?’ I asked. He nodded and motioned for me to come inside. I then went upstairs and found him dressed as Where’s Waldo, passed out on his bed.”

Eva, 22: “We were just having sex while he was fully soft, but I was moaning and pretending he wasn’t.”

“One night during Halloweekend, I was dressed as a pirate when I met this guy at a party. We hit it off, and TBH, he was really cute and tall, which was a plus. We went back to his dorm and hooked up, but it was just awkward. He was legally blind and wore insanely strong prescription glasses, but when we were hooking up, he took his glasses off. And it was obvious that he couldn’t see a thing — he was just staring at the ceiling the entire time we hooked up. Plus, he was my second body, and I was so inexperienced. Eventually, he asked for head, and I obliged, but he just finished himself off after some time. Funnily enough, he fell asleep blasting Lil Peep, and in the morning, when I found out he was a Republican, I never saw him again!”

Tessa, 22: “The owner of the house ended up giving us their parents’ bedroom.”

“We were at a house party, and we hooked up at our friend’s place. They set us up in this bedroom, but we didn’t know whose it was. But then someone tried to bust down the door. Whoever it was was either way too hammered, or crossed or something, and ended up kicking down the door. They ended up running away, and we had to find him. And while we were trying to find them, this girl tried to tell my boyfriend that I was cheating on him with another guy, but I was really just trying to find the person who ran off after they kicked down the door.”

At the end of the day, Halloween isn’t really about clean hookups, smooth moves, or fairytale endings. But that’s the beauty of it: no matter how messy, spooky, or unexpectedly iconic, these nights turn into the stories we laugh about for years. So, whether you’re out hunting vampires, frat boys, or maybe just free drinks, remember, Halloween hookups might not last, but the lore? Legen — wait for it — dary.