Humpday Hookup Horror Stories: Stay With Me


If you’ve got a Humpday Hookup Horror Story, submit it to support (at) postgradproblems (dot) com. Try to keep it less than 500 words. All submissions will be made anonymous. Thou shalt not judge, lest ye be judged.

The Other Man
“Brandon” from St. Paul, Minn.

Let me start off by saying this is a story full of comedy, horror, and shame. I was back home for the Christmas holidays on my way to meet up with friends. All of the sudden, a very attractive old hookup called me up and wanted me to come over. I thought, “Well, I have enough time to kill for a quickie. My friends would understand if I’m a little late.”

I got to her house and she needed to go to the gas station first before we did the deed. While we were there, a hobo came up to us and asked us for money so we politely said no. As we walked away, he grabbed her purse. She started screaming, so I put in a nice right hook to his face. Then we decided to head back to her house. Like any high maintenance, overly dramatic girl, she couldn’t stop crying and freaking out. And on top of all that, some guy she had been friend-zoning for a long time started calling her nonstop (he hates my guts, by the way).

I finally calmed her down and we got down to business. After we shed some clothes, at the very moment of insertion, the guy she had been friend-zoning just decided to stop by. He walked in on us–my hands were on her boobs and everything. So he was mortified by this image and we both freaked out and put our clothes back on. He was upset like a little girl and refused to leave. I sat by myself in the bedroom for almost a half hour and decided this guy had enough, and that it was time for him to leave.

I walked in the living room and those two were arguing about how he loved her. Just really pathetic. He saw me, came over, and pushed me. For the second time that night, I punched someone out of pure instinct. I started to apologize, but she told me to leave. So I left. I went to meet up with my friends and told them the whole story. I’ve never seen my friends laugh harder.

Stay With Me
“Thomas” from Oakland, Calif.

This was a really, really rough wedding season for me. I had seven nuptials in less than three months. I had my last one a few weeks ago, and it was the crowned jewel of the 2014 wedding season. It was at the Casino Ballroom on Catalina Island–probably the nicest, most expensive wedding anyone in my family has ever been to. Shit, it was probably the classiest thing I’ll ever do in my life. I labored through the summer with this weekend in mind, and by the time it rolled around, I wasn’t going to hold back.

So, after dropping roughly an entire paycheck into attending this wedding, I drove down to L.A. on Wednesday. If you get married at the Casino Ballroom, you and your family can afford to take a week off work to celebrate your wedding. I had a big family dinner on Wednesday night, played golf at the Riviera Thursday, went to the rehearsal dinner Friday, and the wedding was Saturday. By Friday morning, I was exhausted and damn near broke. I wasn’t even sure how I was going to get back to my hometown on Sunday. I met this gorgeous bridesmaid at the rehearsal dinner on Friday. She was an L.A. nine, and she was into me. We hit it off that night and shared a cigarette later in the evening, talking about how excited we were for the wedding and how we’d never seen something so extravagant.

The wedding day comes and goes and I find myself yet again talking to this smokeshow, completely hammered. We head back to the hotel and hook up. I wish I remembered it. I woke up around 8 a.m. and she’s getting ready to leave. Still drunk from the night before and all caught up in the romance of the weekend, I begged her to stay. She wasn’t having it, but she was still being flirty. This is where I blow it.

She’s getting ready to leave and I decide it was a good time to start singing. I am a terrible singer. I start singing Sam Smith’s “Stay With Me.” For some reason, I thought it was incredibly appropriate and this girl would hop right back in the sack with me and marry me six months later. Instead, she starts laughing uncontrollably and quickly puts her dress back on. She was out of the door before I could even try to cover it up as a joke.

The things we do when we’re desperate.

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