Welcome to Great Moments in Drunken Hookup Failure, where we showcase five heartwarming true stories of drunken love gone horribly awry. Off we go.
So this one night during my senior year my buddy and I went to a party. After all options were exhausted, we slunked back to my cold Village Cedar apartment. On our way into the building, my buddy and I struck up a conversation with some drunk girls hanging out of a second floor window. One was decent looking, and it was 4:00 a.m., so why not.
When we got in the apartment, the girls were blasting "Farmhouse" by Phish so loud that we had to yell just to make conversation. Somehow, a third girl was asleep in a nearby bedroom. As the song played over and over, my friend and I spit our horrible game. Since I was in a rut, my friend let me take the hot one. We started making out and eventually, the dud went home, and my friend, went back to my apartment and passed out.
After some light petting and nasty makeout sessions (she was a smoker), I went in for the kill. She grabbed a condom and being the drunk asshole that I was - I decided I would make love to her while listening to Phish on repeat even though I didn't know her name. Since this lovely lady was such a nice person, she turned the music up even louder as to not disturb her sleeping friend. As a result, the sleeping roommate came out to yell at us mid-bone. There we were completely nude, on the couch having very bad sex because I barely knew how to use my penis. Sweet. When the roommate went back to bed, my lady friend turned the music up again. Of course, sleeping roommate came out again screaming and yelling. This happened three times which isn't awkward at all when you are completely drunk and have a flaccid penis.
After the third interruption, my lady friend turned the music off and went to apologize to the roommate. I wasn't the kind of guy who gets discouraged easily, so when she came back, I went back to work and nine-to-fived that thing for a few minutes before the girl looked to me and said "Wait, who the fuck are you and why are you inside of me?"
I immediately freaked out because I didn't know she was that drunk and felt like I was taking advantage of her. Still, I was nearly blackout myself, only sober enough to know I had to leave before she called the cops, or another male figure to come kill me. I quickly asked her if she remembered my name or where I lived (the apartment right below her). She said "no." So I told her I was "sorry" and ran out of her apt with my pants and shoes in hand. I ran downstairs to my apartment and burst in the door only to find my buddy waking up from his hour-long nap - ready to get up and go to work. (It was like 6 by this point).
He looked at me carrying my pants, grabbed his keys from the table said "Big Gulps eh? Welp See Ya Later" and walked out the door.
(About three months later my parents were up with my grandma to take me to dinner. They were waiting in the car by the street. As I came out of the apartment complex, that same girl was walking in. It was the only time I ever saw her and she gave me the strangest look. She completely craned her neck. When I got into the car my grandma said "that girl is cute you should go talk to her".)
"Hey, remember me? We kinda raped each other that one night… surely that rings a bell."
Last year my company gave me my first Blackberry, and along with it a new phone number to be used only for business things. Fast forward to the weekend when I start sending out feelers via text to anyone and everyone I believe I have a shot of hooking up with. One evening I get a response from a lady who I had hooked up with me once or twice before, asking who it is as she obviously didn't recognize the number on my new phone. I let her know it's Josh and inquire about her plans for the evening. She is happy to hear from me and indicates she'd like to see me later. Things are looking good!
2 AM rolls around and I send out the inevitable booty text, to which she is more than receptive. I haul ass to her apartment, and having only been there once or twice before have no idea what unit number she lives in. I quick text clears that problem up, however she is surprised that I don't remember which apartment it is. I finally reach the destination and confidently knock on the door, and she opens the door with a look of shock and confusion and invites me in. We settle into the living room, and she strangely takes a seat in an armchair opposite the coach I have parked on. The awkward levels in the room are sky rocketing as we participate in some belittling small talk, until finally she informs me that when she heard from "Josh" she had someone else in mind, as in her ex-boyfriend. After that bomb was dropped she just sat in the living room staring blankly at each other before I left her apartment and my pride along with it.
In the late 90's, while I was myself an undergrad, I was working in a bar on Cape Cod. It was a small town, and while the bar was a tourist trap of sorts, in the early and then late summer, even on weekend nights it was mostly inhabited by college students who were home for the summer. There was one smoking hot girl that I went to college with that was a native of the town. She was a friend of a friend at school, so I naturally rolled out the red carpet to impress her by (a) getting the bouncers to accept her ridiculously fake ID and (b) basically feeding her free drinks all summer long. The whole time, I couldn't help but think that this was the stupidest attempt I'd ever make to fight out of my weight class.
As the summer wore down, and I was getting ready to go back to school, I didn't see her for about a week or so and I figured my fears were realized (and justifiably so), but she came in the last night I was working before heading back. The bar's practically empty (with the exception of a couple of muscled Jersey boys- we'll get to them) , we're having a good time, and she mentions that her folks left that morning and she had the house to herself and asked if I wanted to come by for a drink after my shift. VINDICATION!!! I could have cut glass with my pants tent!
Not 2 minutes later, a fight breaks out behind where she is sitting at the bar, and just as this poor girl is turning around to inspect the commotion **SMACK** the guy's elbow hits her right in the nose. It appeared as if someone had hit her in the face with a balloon full of blood. She freaks out and bolts. All hell is breaking loose, so I can't just leave and give chase, and having no phone # or anything, had to wait until about a week into the next semester to bump into her on campus. When I did, she had bandages from a rhinoplasty on her nose and matching raccoon bruises under her eyes. Needless to say, nothing ever happened and her attitude towards me for the remainder of our acquaintance could best be described as coolly polite.
This was about 10 years ago during my sophomore year at college. I was living in a shitty fraternity house at the time and our rooms were about 10 feet squared, so we had to get pretty creative in cramming all of our unnecessary shit that we couldn't live with out in there. Naturally being the fine craftsman that I am, I constructed the world's most indestructible loft. Rather than sleeping in this loft, I put floor decking on it and slept on a futon that was positioned next to it, essentially creating a second floor, which at the time, I thought was fucking amazing. Fast forward to about a month later at around 2 am post party at which time I had actually secured a lady to hook up with in my prison cell sized love palace. With the lights off, we start getting busy on the futon and when the time comes, she asks "do you have a condom?" FUCK YES I DO.
I race up the ladder to my dresser which I keep up on the "second floor" loft to fetch the glove. Sitting on the edge of the loft in the dark, stark naked, I put on the glow-in-the-dark condom and rather than going back down the ladder to get my apple pie, I decide I am going to impress this lucky lady. I butt-scoot-jump off the side of the loft. The weight of my legs and lack of athletic ability ensured this would end in disaster. I fall, my legs flip to the underside of the futon and I go belly first. So from the girl's perspective all she can see is a dick, glowing in the dark, falling towards her. I fall on the side of the futon and smash the armrest that is made of wood.
Two of the decorative balusters perfectly split on either side of my abdomen, and I groan in pain as I don't realize it quite yet, but I have indeed cracked two of my ribs. If I had landed perhaps an inch to the left or right, I would have been impaled. The girl, naturally freaked out, flips on the light, asks if I'm okay, then gets dressed and says she needs to leave to make sure her roommate got home okay. I was left there to ice my ribs and contemplate masturbation (who am I kidding, I wasn't going to waste that condom, no clean up!).
I am with my girlfriend (let's call her Ann not her real name) in my late teens'. Her dad worked nights and her mom was always drunk and would pass out around 9ish most evenings. When this happened I would get the call from my girl to come over so we could do the deed. She would leave the back door open and I would sneak in.
Well, one night I get the call, I head over, and go into Ann's bedroom. Her mom is as usual passed out in her own room. Ann and I are both bare ass naked and I am right about to commence insertion when I hear my girl's bedroom door open. I do a stop, drop, and roll from the bed into the walk in closet, fully erect with a condom on Mr. Happy and quickly slide the closet door closed.
Her mom had woken up and had decided she was going to have a conversation with her daughter over god knows what. Being a teenage girl of a drunken mother, Ann didn't get along with her mom. So as per usual, any talk they had eventually turned into an argument. (Mind you my girl is naked as a jay bird under the covers arguing with her mom over god knows what.)
The argument and I am not kidding lasts a half hour in her room. The whole time I am in the closet hiding, now flaccid (condom still on however), and trying not to make a sound as I don't want her Mom to see me in my birthday suit. Eventually, the argument ends and her mom exits the room. Being a teenaged, horny boy I figured I would still try to get some from Ann. As she was already angry this just angers her more and she tells me rather loudly to leave. I have one leg in my cavaricci jeans (they were all the rage in the early 90's) when her mom hearing the ruckus walks in again.
I then have to get dressed, and do the walk of shame out the door, with a case of teenaged blue balls. I was banned from her house and Ann broke up with me a couple weeks later. The worst part is that it would be years until I would have sex with the same kind of frequency as I had with Ann.
A tragedy we'll surely never move on from. At least no one was listening to Phish.