Welcome to Great Moments in Drunken Hookup Failure, where we showcase five heartwarming true stories of drunken love gone horribly awry. Off we go.
I went to Vassar College, which housed an inordinate amount of future TV/Movie stars during my tenure. (Marguerite Moreau from Mighty Ducks and most recently Mad Men, and Jonathan Togo from CSI: Miami among them; I've even proudly seen my freshman year roommate kicking a copier in a MNF commercial.)
Vassar also had it's own on-campus bar and almost zero relationship with the town of Poughkeepsie, which means most of the student population was in The Mug on a given weekend night. The added perk of bartender friends giving out nearly free drinks also helped. During my junior year I dated a great girl for a little while, then screwed it up by hooking up with her friends (not good). A year later I'm a senior, I'm blind drunk, and I see her in The Mug and decide it's time to hook up again (not correct).
I saunter/stumble over and give her my best garbledygook pickup line, which probably sounded like a cross between Steven Wright and a lewd, drowning hippo. To which she soberly responds, "I'm dating Justin now," and points beside her. And there he is, Justin Long, before the Dodgeball/Mac ads/Drew Barrymore fame. My response? "Really? THIS guy?! Are you serious?" In a shocking turn of events, we did not hook up that night. And now, every time I flip by Live Free or Die Hard on FX, I think, "Really? This fucking guy?"
Brutal. I've shifted a great deal of my Jimmy Fallon hatred over to Justin Long. It just makes sense.
This was in freshman year of undergrad. Some friends were holding a party to watch our team's biggest game of the year. Suffice to say, we got blown out. By the 3rd quarter I was downing beers as fast as possible to make the pain of losing go away while yelling obscenities. I decided to peel myself off the couch to go mingle, refill my cup at the keg, and try to get some action from the fairer sex.
I turn around and a group of 3 girls I've never seen before walks in. I introduce myself by yelling "HEYYY" and get them some keg cups. I start talking to one of the 3 for a bit, she is short and cute. Her friends see where this is going and promptly separate from us. Within 10 minutes she and I are making out. Hardcore. In the middle of the room where everyone else is sitting and watching the game.
She goes to a neighboring college about 2 miles down the road; we thus go back to my dorm. Luckily, my roommate was gone for the weekend. I open the door to let her in. By the time I close the door and turn around, she is somehow already naked in my bed. I hop in and things get going well, but I remember I am out of condoms. I inform her of this, which she is fine with and begins going down on me.
Now, she was doing well on me, but I come to the realization that while I am hard, there is NO WAY that I'm going to finish. I decide to just let her keep going and hope maybe I'll finish. For over 20 minutes. I lay back and think how good this is, having a girl blowing me for a while, after the night started pretty badly. But then it hit me: The spins.
I had indeed had a bit too much to drink, as I was getting the drunk spins as I laid back. I try putting a foot on the floor, but room is still spinning. I am thinking happy thoughts and just trying not to puke. This works for about 2 seconds before my body says that this stuff is coming up.
I throw her off me (She's still been working on me) and sprint to the garbage can in the opposite corner of my room and heave up a night's worth of cheap beer and pizza. I spend a solid minute projectile vomiting. It was one of THOSE pukes. I laugh to myself as I see that even while puking, I still maintain my boner and it had been poking my stomach through the heaves.
I get up, wipe off my mouth with my forearm and turn towards her. She is silent. I saunter over towards her and put a hand up on the wall to look cool. In a kinda seductive voice, I say to her, "So, where were we?" Her face is one of pure repulsion and horror. She only stammers "..I..I, uh, think maybe I should go home now?" It is only then that I realize the ridiculousness of what I just said, agree with her, and walk her out of my building.
Gotta admire our boy's moxie.
In college I was in love with this girl Michelle. We hung out a lot and she invited me to sleep over many times and I would sleep over IN HER BED WITH HER but I was a huge pussy and never hooked up with her. One summer, her roommate Melissa had a party at her parents' house. I was excited about the opportunity to see my Michelle (who lived out of state) over summer break so I convinced my friend Dan to come with me on this 45 minute drive to a party where I would know 2 people and he would know zero.
By the time we got there, Michelle was already passed out in some upstairs bedroom. She had been playing beer pong and smoking weed and puking all night so she was just totally out of commission. When we decided to leave I went to say goodbye to Melissa, the host of the party, who (don't forget) was Michelle's roommate all through college. She drunkenly insisted that I could not leave yet, we barely had a chance to talk. Before I even realized that she was coming on to me, she started jamming her tongue down my throat. We made out for quite some time while my friend Dan just stood there with his jacket on, waiting to leave. I ended up telling him to sit tight for a while cause I wanted to hook up with this girl.
At this point it was pretty late so all the beds and couches were occupied. We thought it was a great idea to set up a couple blankets in the upstairs hallway. We weren't even the only ones hooking up in that hallway. It was a pretty sloppy night all around. I took about a million years to get her jeans off (tight jeans are the worst!) and she didn't have much luck unbuckling my belt. It's always an embarrassing hookup moment when somebody has to take their own clothes off.
So after I unbuckle my own belt and pull my own pants down around my ankles she starts giving me this weird reverse hand job. Like her hand was clasped around my dick in such a way that her thumb and forefinger were at the base and her pinky was up near the tip. It soon became obvious that this wasn't some thrilling new technique. She just didn't know what she was doing. This is how I imagine every girl I've ever hooked up with felt when I tried to finger them.
At one point we agreed it was a good idea to have sex so I started trying to get my semi-aroused penis into her semi-aroused vagina and a bedroom door opened up right next to us. It was Michelle, the girl who I was in love with, the girl who I really WANTED to hook up with at this party. She was finally done being passed out and had to use the bathroom across the hall. When she saw me and her roommate awkwardly going at it under a He-Man blanket on the floor she just said 'HA!' and walked into the bathroom. I immediately realized that A) I looked fucking ridiculous and that B) I would never have a chance to hook up with her again. And I never did.
Ah, the claw grip. Always a fun thing to experience. Has anyone ever received a GOOD handjob?
A friend of mine and about 15 friends were renting a house on the beach in New England for a couple of weeks in the summer. I was invited to join them for a weekend. The place was crowded, maybe only 4 bedrooms or so, so the beds were all full and there was a lot of cramming sleeping bags on the floor.
The second night, everyone is getting really drunk by a fire pit they have. At about 2am, the most beautiful girl in the group (tall, slim, long-naturally-large-curled blond hair, lip ring - way out of my league) announces she wants to go swimming. Who wants to go with her? I do! Once we hit the sand, she starts stripping her clothes and running into the ocean. I follow her lead. The late night nude swimming inevitably leads to late night nude making out in the Atlantic Ocean. Honestly, despite the fact that I didn't know her name, it was probably the most cinematically romantic moment of my life. Snogging under the full moon as the waves crashed down around us. I mean, right? (Although in the movies, you never see the boner poking into her lower abdomen - is that embarrassing or flattering?)
We'd had enough "swimming" and it was time to head back to the house. When we got back, everyone was already in bed, and neither of us had established our sleeping quarters for the night. Someone gave me the idea to drag a mattress into the top floor bathroom where we could have some privacy. She agreed. We were there together for a few minutes, when I decided that I should go to the bathroom (elsewhere). She was going to stay and wait. While I was gone, I got the even more brilliant idea to take my contact lenses out before I fell asleep in them, which involved finding my luggage in the dark, finding the stuff, going down like 3 or 4 flights of stairs to get to a free bathroom, and so on.
Well, you get the picture - I took too long and when I got back she had vanished from the mattress on the disgusting bathroom floor to go sleep like a normal person would. When I asked her about it in the morning, she claimed she thought *I* left, although from the awkwardness and avoidance the balance of that day, it was clear that she felt she dodged a bullet. The moral of the story: don't ever give a girl a free second to reflect on the mistake she's about to make.
Oh, Christ. That SUCKS. Now I'm pissed. You give a woman ANY open window, they flee. What gives, ladies? This is why we men always have to throw you in car trunks.
Sophomore year of college, I'm at a house party with jungle juice and meet a girl and I'm way too drunk to remember her name. Stuff happens. An hour later we're back in her dorm room messing around, with no light except for what's coming from the Ronco infomercial on her 12" TV. I slide her panties off as I go downstairs.
Then it's... wait a second.
The entire right side of her pubic hair is smooth and freshly shorn. The left side has enough growth to stick together and curl. We're talking all along the side and up to the top, straight down the middle. She has a hemispheric bald vagina. Here, I drew a picture.
I look up at her, confused.
"What?.." [reaches down] "OHMIGOD! I'M SO SORRY!" Then she runs out room after grabbing a towel and darts to, I guess the bathroom? Somewhere else. After like ten minutes of waiting there I just up and leave. Never saw her again. It's not so much that it was a failure.. it's that for the past seven years I've been completely unable to come up with ANY explanation as to why.
I worked at an ad agency once with a dude who had half a beard, and the half beard he did had was braided on the bottom. And he was a white person. I'll never understand why anyone would ever do that. FIX YO ASYMMETRY!