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Humpday Hookup Horror Stories: Roommate Drama

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If you’ve got a hookup horror story, send it in using our submission form, and be sure to select “Column.” All stories will be made anonymous. Try to keep it under 500 words. Thou shalt not judge lest ye be judged.

Roommate Drama
“Bryan” from Austin, TX

I went back home to Chicago for Thanksgiving and partook in Black Wednesday activities, as is tradition. After living in Austin for two years after graduating, it was just my second time back home for a holiday. I saw people that I hadn’t seen in years. The nostalgia was overpowering at times.

After pregaming at a buddy’s house, we headed out to the bars and got the night started. I had one of those feelings before the night began that I would be hooking up with someone. I don’t feel like a douche saying that, because I’m pretty certain everyone had had a brush with sexual intuition. Sure enough, around midnight in Wrigleyville, I ran into the chick I lost my virginity to. The years had been kind to her. We ordered shots and drank beer until the bar closed.

We headed back to her place after the bar closed. Without getting into much detail, the cabbie wasn’t too happy with what we were doing to his backseat, but we just kept going at it anyway. We pulled up to her place, I gave the cabbie a nice tip for being such a gentleman about everything and we headed upstairs.

We burst into her apartment, making out and about to tear each other’s clothes off, when I heard the worst noise you can possibly hear pre-hookup: a woman crying. Her roommate was on the floor, in her underwear, sobbing uncontrollably. Naturally, the nurturing began between the roomies. I took a seat on the couch and watched it all unfold.

In between blubbering and gasps of air, I deduced that the roommate saw her ex-boyfriend and his new girlfriend at the bar, and the ex’s new girlfriend was much prettier than the roommate. We were in for a long night. The two went back and forth with a dialogue that was more dramatic than a Nicholas Sparks movie. Apparently the roommate tried to tell the ex-boyfriend that she still had feelings for him, and the boyfriend shot that idea out of the sky repeatedly, and then she got confronted by the ex-boyfriend’s current girlfriend and was eventually thrown out of the bar for causing a scene.

Two hours later, the sobbing roommate had been neutralized and we headed to her bedroom. Then, she laid it on me. “I’m so tired. I’m so sorry. Maybe we can try in the morning?”

That wasn’t gonna happen. My family is one of those weird families that starts Thanksgiving at 11 in the morning, and I wasn’t about to show up to family Thanksgiving in a cab. So I piled out of a cab in front of my parent’s house at 4am, and just like clockwork, my mother was there waiting to lay the Catholic guilt on thick.

Women, right?

Ice, Ice Baby
“Jess” from Washington, DC

This happened a couple of years ago, but it is the absolute definition of a “Hookup Horror Story.” I met a really cute guy at a bar one night and we decided to go home together after a long night of drinking.

It had snowed earlier in the week, but it warmed up and the snow melted during the day, leaving everything covered in that disgusting, half-ice, half-mud mixture and making the sidewalks almost unwalkable. Of course, while we were in the bar, all of that stuff froze over and made the sidewalk outside the bar into a sheet of ice.

So naturally, I’m all over this guy as we leave the bar, take one step out the door onto a fresh patch of black ice, my knee buckles under me and I nosedive right in front of him. Others rushed to my aid, but like a true gentleman, he scooped me up and loaded me into the cab back to my place where we then hooked up. He even carried me up the stairs to my apartment. Swoon.

The next morning, I woke up and my left knee was the size of a melon. I freaked out and looked next to me. My former mate had left before I woke up. Chivalry is dead, and so are guys who like morning sex too, apparently, not that I was in any condition to perform.

So I went to the doctor later that morning to see what was wrong with my knee, which was still swollen to twice its normal size. I got an MRI ($1,600 bucks) at the hospital and sure enough, my knee was torn to shreds. A torn ACL, MCL and a broken patella.

Total surgery cost: $17,000 dollars. Only half covered by my insurance. I’m still paying it off.

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