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You're Not As Cool During A Hookup As You Think You Are

Welcome to Great Moments in Drunken Hookup Failure, where we showcase three heartwarming true stories of drunken love gone horribly awry. Off we go.


It was the summer after my senior year of college, and I decided to have one last hurrah with all of my friends before we went our separate ways. What better way of doing that than throwing a kickass 4th of July party? After all, I lived in one of the most ideal locations to view the fireworks in Pittsburgh.

We started the drinking marathon at 11 in the morning, and it went all day and into the night. By the time the ladies arrived, it was around 6, and lo and behold, one of the girls that I wanted to hook up with my entire 4 years of college is at my party. Michelle. I knew that this would be my last chance to hook up with her because she was on her way to grad school in another state. After a while, I was able to find a simple way of extending an invite to my room, and she accepted. Walking up the stairs behind her, staring at her marvelous assets, realizing that I am about to engage in an activity that I had wanted to do for 4 years, I became overly excited.

We hopped onto my bed and started to make out. It was July, and there was no AC in my house, and my upstairs bedroom became a little hot and steamy. I decided to open the window next to my bed. As I opened the window, I saw that all of my friends that assisted me in a huge way with this operation were on the patio in the backyard below me doing keg stands. Perhaps if I had not been completely shithammered, I would've opened the window and then gotten back to Michelle. But, sadly, that was not the case.

My bed was along the wall, so after I opened the window, I laid on my back, and kicked the screen out of the window onto those still partying outside. I then leaned out the window and yelled, in my best version of Dave Chappelle's Rick James voice, "IT'S A CELEBRATION BITCHES!!!!" Then, Michelle leaned out the window next to me, and as soon as she showed her face to the crowd below, all of my friends erupted like they were at a Pens game and Sid just won the Cup with goal in double OT.

Again, if I wasn't totally obliterated, I would've remembered that not 30 seconds before, I opened the window to try to cool the room down. However, after I showcased what I was about to conquer, I slammed the window shut. And to my surprise, Michelle's fingers remained on the window sill. Instantly, I was deafened by her shrieking "AHHHHHHHHHHHHHHHHHHH!" I had no idea what happened, but I looked down through the window and saw all of my friends pointing and laughing their asses off. They told me later that all they saw were her little fingers wiggling around, and her screaming. Anyway, I quickly lifted up the window, and saw her bloody fingers, all 8 of them. She ran to the bathroom, washed them in agony, grabbed a towel, then grabbed her friends, and left.



In high school I had a crush on Jess. I was, and still am a big loser so my game consisted of gawking at her from afar and talking to her friends about how much I liked her in the hopes that she would find out. Eventually she found out I liked her and wasn't repulsed which gave me the courage to ask her out. My parents were going out of town so I figured I could bring her over to my house for some alone time. Once the plan came together I nearly shit my pants with anxiety because I had never had alone time with a girl at my house. I had nearly a week to plan and the best I could come up with was to rent the movie Clerks to watch on VHS in my living room.

So the actual date: I picked her up in my mom's Camry, drive her over to my house. On the way over I mention several times how my parents are away and that it's a borrowed Camry, like that would make it less bad. We get back to my house and walk into the living room and she sits on the couch. I put in the DVD and then go and sit in some shitty IKEA chair that every kid had in college on the far side of the room. I don't know why I did it. But that's how we sat for the duration of that movie. Not saying a word, sitting 10 feet from each other. Afterwards, I got up and suggested I take her home thinking I would make my move in the car. When I pulled up to her house she quickly got out, and said Clerks wasn't her type of movie, and ran to her door. I went home and JO'd to bad porn.


That's every date I've ever had right there.


In 2005, I went with some college friends to NYC to see my friend's band play at some dive bar and hang out. After his show, about 12 of us hit the bars and proceed to enjoy the nightlife NYC has to offer. One of the people with me was my college roommate's friend from home who happened to be in the Army and thus, had no sense of remorse. After a couple hours of drinking, most of the people I was with had left to go back and stay in the HoJo hotel room we booked (One NYC boutique hotel room for 12 people and it was still costing too much for a bunch of college kids).

The friend, who I had met and hung out with several times before, begins chatting up an older woman and her daughter. I'm not ready to go in for the night so I decided to stay back and keep drinking and see where the night took us. We separate our conversations with our respective partners (him with the mother, me with the daughter). The ladies say they are heading back to drink at their hotel bar (The W Hotel) and we decide to walk them back and grab a couple drinks as well. The mother looked pretty good for her age (probably mid-40's) and the daughter was pretty fresh out of college herself and was cute enough but I wasn't thinking any of this would lead to anything.

As the daughter and I are drinking at the W bar area we notice that my friend and her mom were gone. Figuring they were getting some food or something, we decide to see if we can hook up real quick in the hotel room she was sharing with her mom. Heavy touching and making out on the elevator proceeds, with several hotel patrons complaining after we couldn't stop before the doors on the elevator opened.

This PDA continues to her room door where she opens the door only to find her mom on her back being railed by the friend. She screams, "Mom!" and begins to run and push me toward the hotel room bathroom. While in the bathroom she tells me that she can't believe my friend is fucking her mom (they stopped when we came in). I tell her we should just get out of there for a while and let things cool off and say we should get some food in the meantime. On the way out of the room, she covers her eyes and I make eye contact with the friend who gives me a two thumbs up.

At this point, I definitely think the night has been shot as I thought that was pretty traumatic for a daughter to see. Not so. She was still ready to do this. We go to a busy diner where we attempt to order food but it is taking too long for her. After we put the order in she thinks we need to leave and just get this deed done for the night. Knowing I had over 10 people in my HoJo room I decide to go to the Marriott beside the W Hotel cause I figured it was my cheapest chance at getting laid and it was about 5 AM at this point. I was wrong. $500 later we are heading up to the hotel room to finally put all the drama behind us. We go to the room and she suggests foreplay in the shower. We mess around and FINALLY get to the bed and start business. This is where the night ends. I had passed out in the middle of it. I was awoken in the morning by my cell phone ringing. It was the friend. He asks, "Hey, is Meghan there? Her mom wants to make sure she's ok."

I walked her back to the W Hotel to meet my friend and cab back to the HoJo. I ask her for her number and she tells me never to talk to her again.


Now that is how you do a DHF story.

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