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


This story goes back to my high school days. I had been dating a girl for several months and things were going great. We had taken it all the way to 3rd base and were doing so on a regular basis as we had her house to ourselves every day after school. I soon started joking around and hinting that we should try the 'ol 69, but she was somewhat reluctant.

Fastforward a few weeks and we were at a friends party partaking in the regular shots, shotgunning, beer pong, etc... Towards the end of the night she whispers in my ear that she's ready to do the deed and to meet her upstairs up on the 3rd floor which was a small, private media room. A few minutes later, half-chubbed, I walk into the dark room where she jumps on me already naked and ready to 69.

I was gung ho from the start, however I couldn't help but notice it didn't smell that great. I figured this must be normal due to the nature of the position and kept at it. After we finished, I hopped up, got dressed, but still had the stench of poo following me around. At that moment, my lady friend flipped on the light as we locked eyes I noticed she was sporting a ghastly face. I crossed my eyes, looked down at the tip of my nose and discovered....

A dingleberry.

She flicked it off and we never spoke of it again. Looking back, that was probably the beginning of the end.


It's my last year in law school and I decide to go on a second date with this girl I met on-line named Mary Kate. We go out to dinner and have a cocktail or three, so I'm starting to feel better about the situation. She invites me back to her place but says "I live with my parents, but we can hang out in my room and watch a movie." After my mostly liquid dinner, this suggestion doesn't phase me.

We head straight up to her room and somehow avoid any interaction with either of her parents. We start the movie and I'm about to sit down on the bed when Mary Kate screams "NO OUTSIDE CLOTHES ON THE BED!!" I don't know what this means, but I decide that if anything is going to happen that night, I should listen. The floor it is. We sit on the floor and just start making out when her phone rings. I can't tell who is on the other line, but she ends the call by saying "I love you." I ask her who was on the line. She says "Oh, it was my mom. She wanted to know if you were staying for breakfast."

When I realized that this happened so often that her mom was ok with it, and happy to make breakfast for the guy, I freaked out and suddenly "remembered" that I had to be somewhere else that night. Probably a good thing because on my way out her mom came to say goodbye, shook my hand, and said "So nice to meet you, Dustin. We've never had a Dustin before." I look over at Mary Kate, who just shrugs. There wasn't a 3rd date.


So there was this girl I knew somewhat from back in high school, named Katie R. She was always an absolute smoke show and my friends and I were kind of obsessed with her. We didn't see her that often since she didn't go to the same school as us, but we would be at the same parties sometimes and I got to know her a little bit one summer when we both worked at the shitty Mexican restaurant down the street from my school. Anyways, nothing ever came of it and pretty soon we both headed off to college in different places.

My story takes place the summer after I graduated college and everybody was back home before leaving again for new jobs and things like that. One Saturday evening a couple friends and I decided to pregame and head to the bars, which we did. The first bar we walk into has a pretty light crowd, and I'm surprised to see Katie standing in the middle of the room with a couple guys. I stop and say hi for a minute as we walk past and she seems pretty happy to see me, which I'm pumped about, but I don't linger since she's with dudes and I have drinking to do.

Fast forward 3 hours and a couple different bars, and my buddies and I are walking into this one spot that stays open later than most of the bars in my area. I'm pretty hammered by this point. Not falling over or vomiting or anything, but definitely not sober. Anyways, we make our way up to the bar, grab drinks, look around, and who do I see over by the dance floor but Katie, who seems to have lost the two guys she was with earlier. I'm way beyond being nervous at this point so I go over and grab her and take her onto the packed dance floor. She seems to be not against this idea. As time goes on she starts getting really into it-reaching for my neck from behind, running her fingers through my hair, I think she grabbed my crotch at one point. So of course I'm thinking, "fuck yeah," and because I'm a classy gentleman, I go for the dance floor makeout. She's into this as well, and soon enough we are full on getting after it on the dance floor. I literally remember thinking to myself "here I am, making out with Katie R, the legendary girl from high school, and she wants to go home with me. I am THE MAN." About this time the lights come on as the bar is about to close, so its time to make my move if I'm going to get her over to my place. As she's turning around to face me I take a deep breath, look her in the eyes, and…

…and it's not her. It's some girl I've never seen before in my life. I must have stared at her at her like an asshole for five to ten seconds before I could wrap my head around this fact, and when I realized what happened I think laughed right in her face. It's not like this girl was ugly or anything; I think she was actually kind of cute, and a rational guy might have tried to keep things going with her, rando or no. But in my drunken state I found it so hilarious that I had been dancing and making out with this chick, thinking I was hot shit for bagging essentially the prom queen, while it was actually some unknown girl the whole time, that all I could do was mumble something and get the fuck out of there before I laughed my ass off.


It was my junior year of college when I had somehow escaped from a doomed relationship and was looking to make up for lost time. There was a girl I had made progress with whom I ran into during a drinking night out and we made plans to meet up at my single room back at the frat house later that night.

Now it's later when I see her approach the house and I abandon my heavy drinking session with my brothers to go hook up. We're barely into my room and our clothes are coming off. In short notice we're naked, standing up against the wall midway between the heavy bedroom door and the window (but the room itself isn't much more than 8-10 feet in length), and my dick is in her hand ready to go.

While I'm already planning where this is headed next, my spurned and jealous drunk brothers call an audible on my night. The coordinated attack happens simultaneously as they rattle my window and kick the door open on us caught in the middle. In that moment, several things happen at once:

-the door swings open right over my big toe, taking part of the top of its skin with it
-she panics for her life, reacting by tightening her grip on my dick and yanking hard as she can
-I scream for the loss of my toe, dick, and dignity

Somehow this response satisfies my brothers and they retreat, leaving me naked with a bloody toe, a mangled dick with serious Indian burn, and an irate female who blames me for leaving her so vulnerable (ok, fair enough), who will never hook up with me again - not that I was in game shape for many days after that.

Seriously, what the fuck is wrong with my gender? DON'T COCKBLOCK FRIENDS.