Humpday Hookup Horror Stories: Parental Supervision


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.

Parental Guidance
“Charlie” from Minneapolis, MN

Whenever the holidays roll around, I’m reminded of this story. My wife (then fiancée) and I stayed at her parents’ house over Thanksgiving a couple of years ago. Her parents are really cool. They were always down to help us out in any way they could. Her dad even loaned me money so I could make a down payment on our first house. They were very understanding and forward thinking. Not that they were hippies or anything, they were just very open-minded and generous for older folks.

So we were eating dinner with her family. It was her mom, dad and two older sisters. Dinner with her family is always fun. They’re a loud, opinionated bunch, but also crazy educated and intelligent. I feel overmatched every time I go over to dinner there, but at the same time, I am endlessly entertained by their dinner table debates over Irish coffee after our meal.

We stayed pretty late at their house that night. The two sisters had already gone home, and we began talking about our upcoming wedding and what our plans were. After another hour of conversation, her mom and dad went up to bed, while my fiancée and I stayed downstairs to do the dishes. Right as I heard her parents’ bedroom door close, we leapt into action right there at the sink.

So we were getting into it in her parents’ kitchen and I noticed something out of the corner of my eye. It was her dad getting his reading glasses in the living room. There weren’t any lights on downstairs, so thankfully he couldn’t see us. That is until he moved into the kitchen and turned on those lights, exposing me and his daughter in the act. My pants were around my ankles and I had my hands on her boobs. It would have been a hilarious scene, except I was absolutely mortified. Instead of screaming and shouting in disgust, he just gave me a wink and a smirk and turned the lights off.

For months after that, I couldn’t bring myself to look him in the eye without picturing that look on his face that night.


We’re Going Down
“Kara” from Chicago, IL

This story comes from back in my college days. I know this site is called Post Grad Problems, but I think this story is too funny/unfortunate/terrifying not to tell. It happened early on in my sophomore year of college. It was probably less than a week or so into our first week of classes. Since it was syllabus week, we were partying every night. One night, me and my hookup buddy were doing what we do in his lofted bed.

In this particular frat house, the beds are all lofted above one another. These “lofts” were usually just made up of 4x4s and plywood. Not exactly stable. His fraternity had thrown a party that night and he and I had snuck away during the middle of the party. I had a ton of friends at the party and I could hear them shouting my name, trying to find me. Well, they found me and all five of them tried to climb up into the loft. Right as the fifth of my friends got in the bed, we heard a crack and then the loft gave way.

We crashed down on top of the bed below us and everyone started laughing. Little did we know that we had come crashing down on someone sleeping in the bed below us. We heard muffled shouting and banging beneath us. We all jumped out of the bed and scrambled to get this poor guy out from underneath the wreckage. He had a compound fracture in his leg and the bone was sticking out of his shin. Two of my friends immediately began puking everywhere and my hookup buddy called 911.

The poor guy beneath us ended up with a broken leg that required surgery, a concussion and a contusion on his arm.

It could’ve been much worse and in retrospect, it should’ve been much, much worse.

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