Humpday Hookup Horror Stories: Always Bet On Red


Since launching the new PGP site, we’ve received several submissions each regarding postgrad hookup horror stories, so naturally we’re going to handpick the worst of the worst and show them to you. The names have been changed to protect the guilty’s career and personal life. Thou shalt not judge lest ye be judged.

If you’ve got a hookup horror story, submit it to with “Humpday Hookups” as the subject, or submit it through our website by using the menu right below the featured posts. All submissions will be made anonymous.

Always Bet On Red
Brendan from Chicago, IL

College had come and gone, and I had never hooked up with a redhead. It just never happened for me. I had my chances once or twice, but could never close. I was determined to make it happen before I settled down, postgrad.

It was my second summer after college, and me and some buddies were headed out on the town in celebration of a friend’s birthday. A girl’s birthday, more specifically. We showed up for drinks and appetizers at a really swanky loft in Lincoln Park. A couple of us hopped behind the bar to serve drinks and get in good with the female crowd. It was one of those perfect nights when girls outnumbered guys and there was plenty of ahem, talent, at this party.

I got myself drunk enough to start talking to the girls in attendance, and noticed a cute redhead eyeing me for most of the night. I couldn’t screw this up. I may not get another chance. After mustering up some courage (pouring myself a double scotch and water), I introduced myself and we started flirting a little bit after a few particulars. Her name was Amy. She had just moved back home after graduating from Wisconsin and was starting grad school at Loyola in the fall.

We hit the bars, got drunk, and long story short, we ended up in a cab together after a long night of dancing and shots.

She wouldn’t go back to my place, so I asked where she lived. Turns out she was living with her parents in Oak Park, an affluent suburb about 20 minutes from Lincoln Park. I couldn’t turn down this opportunity. So a $50 cab fare later, we arrived at her parents’ house.

Her house was massive. It was a legitimate mansion. We snuck in through a back door and wound our way through endless hallways, finally getting to her room. I had closed on my first redhead. We finished up after a couple rounds of sloppy, near-blackout sex, and she passed out as I went to the bathroom and planned my exit strategy. Again, this house was massive.

I was still very much drunk at this point, and stumbled my way through the hallways trying to find my way out of the massive mansion. This place was like Wayne Manor, with long, twisting hallways and multiple staircases. I finally got down to the first floor as the sun was coming up and heard voices coming from the kitchen. Her mom and dad were already awake and eating breakfast, blocking the only exit out of the back door.

I panicked and made my way towards the front of the house. The front door was locked. No key in sight. I looked towards the living room that had big French doors that led out onto the patio and decided to take that route. After opening one of the doors, the house’s security system rung, letting mom and dad know a door was open. I was home free, until I realized I was trapped in the back yard, with eight-foot tall fences everywhere I looked. Next thing I knew, her dad was staring me down in the back yard. He yelled inside for his wife to call the cops and started moving towards me. Fight or flight kicked in, and I darted toward the fence, leapt over it, and landed on the other side with a heavy thud, then twisted my ankle after clumsily picking myself up.

I hobbled into the street towards a main road, praying that her dad wasn’t hot on my trail and also that I’d be able to find a cab so far away from the city. Miraculously, I found one after about a quarter mile’s walk on the nearest main road. A total of $100 dollars in cab fare later, I crashed into my bed around 7am.

She called me a couple of days later, telling me the story about her parents telling her the story of the crazy guy they found in their back yard on Sunday morning. We had a good laugh about it. I still see her out on the town from time to time.

Family Ties
Grant from Dallas, TX

My cousin had just graduated from TCU and his family threw him a huge graduation party to celebrate. There were at least a hundred people in attendance and they had a really awesome tent setup in the backyard with an open bar and barbecue buffet.

After making the rounds and meeting a few new people, my aunt called me over to re-introduce me to one of their close family friends. She was a gorgeous, blonde MBA student at SMU. I had noticed her before at some of their family functions, but hadn’t seen her in a few years. She had really come into her own in her 20s. Her name was Lauren and she was the total package. Smart, funny, a total smokepiece and I could tell she liked to get drunk. We talked for a few minutes, and as the party was dwindling down, a party bus showed up to take us all to a few bars around town.

Lauren and I hung out alone for most of the night, sitting at the end of the bar, taking shots when we weren’t grinding it out on the dance floor. This girl was a champ. She went round for round with me until around one in the morning when we decided to ditch the party and head back to my apartment. As we were hailing a cab, my cousin was being carried out of the bar by a group of his friends. I told everyone I would take care of him and get him back home safely, sacrificing a surefire hookup with Lauren to take care of my belligerent cousin. I loaded him into the cab and as I was giving the cabbie directions, Lauren hopped in the cab with us, saying she needed to get her car, despite being in no condition to drive. My cousin passed out, and Lauren and I continued to hit it off in the cab until we got back to the house.

After we got him into bed, we headed back downstairs. The cab had already left and we couldn’t get another one to come get her to take her back to her place, so we just decided to spend the night at my aunt and uncle’s house. I went down to the basement and made myself a bed on the couch and Lauren took a bed in the guest room, which was also in the basement. I watched a little TV and then fell asleep around 2am. Just a few minutes after falling asleep, I woke up with Lauren’s lips pressed against mine and her hand down my pants. “Hi,” she seductively whispered into my ear. It was on.

She was a pro. It was obvious. But she was a little too into it. She started moaning loudly. I tried to calm her down and get her to be quiet, but she was so drunk, she couldn’t contain herself. She kept shouting my name like I was some sort of demigod.

“Grant! Oh, Grant!”

Too loud. Way too loud.

“Grant! Yes! Grant!”


The second voice was all too familiar. It wasn’t Lauren shouting my name in ecstasy, it was my aunt shouting my name in pure disgust. Lauren hopped off me, naked as the day she was born, and scampered back to the guest room.

After a lengthy discussion about respecting their house, my aunt finally left me in the basement and made Lauren go sleep upstairs.

The next morning, I had the most awkward breakfast of my life. My cousin was in the throes of an atrocious hangover, I was suffering from a devastating case of blue balls and my aunt was staring me down the entire time as Lauren and I sat next to one another in shame.

We ended up going out on a couple of dates and were really into one another, but she started dating some guy at SMU the next semester. Ah, the one that got away.

You have a Hookup Horror Story that you’d like to submit? Use our submission form on the home page or send them over to Keep it somewhat SFW. Submissions will remain anonymous.

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Brian McGannon

What do I love? I love happy hour, a good golf tan, and getting moderately drunk during dinner.

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