Failure At The Mile High Club

Illustration for article titled Failure At The Mile High Club

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



I was lucky enough to be matched up with a roommate in college who was from Las Vegas. After our freshman year my other roommate and I planned to take a trip out west to spend a weekend in Vegas and then drive out to Los Angeles where another of our friends was from. We met in Philly and being pre-crazy liquid rules brought a twelve pack of beers into the airport. We are only 19 at the time so taking turns shotgunning them in some sketchy corner seemed like the best idea. By the time we get to the plane we are wrecked.

We were flying Southwest (you pick your own seats on a first come basis) so while standing around waiting to board a cute girl, we can call her Amy, approaches. She gives us a story about some guy giving her weird eyes and asking if she could sit next to us. "It would make me a lot more comfortable." Of course! Who would turn that down? I have a girlfriend at the time so I immediately go into wingman mode. So we board - I am on the window, my buddy in the middle, and her on the aisle. The creepy guy continues to look over and is visibly getting more and more agitated but we think nothing of it, we're drunk and there is a small blonde with giant tits interested in talking to us in a confined space for 4 hours.

We order a few more beers on the plane via some elderly flight attendant who gave us the "are you boys sure you're 21?" question. After two more beers I fall asleep. I awake thirty minutes later to my roommate and Amy going at it. They are sucking face, her hand is giving him an over the pants handy, and I hear her whisper, "Do you want to meet me in the bathroom?" Now my friend, an aspiring lawyer, intelligently declines, but makes plans to meet up in Las Vegas.

I perk back up and make some small talk. She comments on how we are light weights and begins making very strange naive statements like "My friends drink straight vodka, so much they get kegs of it." Being an asshole, I immediately burst into laughter and call her on this stupidity. She then looks at our fake IDs and tell us how shitty they are (they were) to which I reply, "Well, show us your ID." She says she lost her driver's license but has an 'old school ID.' She proceeds to pull out an 8th grade student ID card. However, my friend is still 100% confident she is at least 17 like she originally said. While on a trip to the bathroom the creepy guy gives him a death-inducing stare and the "I'm watching you" fingers.

The story caps off by a change of numbers and a smooth landing in Vegas...until baggage claim where she proceeds to grab my buddy's hand and drags him up to her awaiting family who greet her and her UNCLE in a warm embrace. He deleted that number as soon as we got to the hotel and to this day refuses to admit had made out with a 15-year old.


So I live in a medium-sized city, where there are a finite number of bars, and unfortunately you often run into the same people when partying. Now it's New Years Eve, and since I've been on a cold streak lately, I'm looking to get down.

After a lengthy pre-game of Red Bull & vodkas we get to the club at 10:30. After pounding a couple shots at the bar, I scour the dance floor looking for single girls ready to get down for one night. I immediately run into this cute girl, Jen, and proceed to grind with her for a bit, while ‘subtly' shoving my crotch into her behind on the dance floor. I grab her number. At this point, I think I'm golden. I have this cute girl's number, and
she's a great possibility to get together after the bar.

Now the rest of the night is a bit of a haze, but at some point I remember running into this other girl, Rachel, who I hooked up with a couple times during the previous summer. We fooled around at Rachel's friend's house, but protocol always called for me to leave efore Rachel's friend awoke the next morning. Nothing materialized from this though, and we had yet to talk since. But a short, "hey, how's it going?" was said from both ends, and I moved on. I find Jen on the dance floor later on in the night. She's grinding me so hard, and even whispers in my ear, "Text me later if you want to get lucky".

So my friend who's DD'ing that night is driving my other friends and I home. On the way I obviously text Jen to see where the magic is about to happen. Her response: ‘Ya, why don't you come over?' I respond: ‘What's your address?' She then texts back: ‘It's the same address where you fucked my friend, Rachel, on my couch this summer. Fuck you! I hope you die. Delete this number you douche bag!'


Freshman year I lived next to a smoking hot, painfully shy girl, Emily. Unfortunately, she had a boyfriend at the time and I was way too intimidated to swoop in for the steal. Sophomore year she had finally broken up with her boyfriend and I saw her at a party and finally approached her. Throughout the course of the next two years, we go to a few cocktail events together from time to time and casually hook up (no banging included). It was nothing serious, we were good friends in a non-Platonic way who I seriously wanted to get in with.

On two different occasions, I had the door wide open. And on two different occasions, I failed miserably and closed the door for all time to come. The first was at another cocktail event. We went to the party, got to our usual level of blackout and made our natural progression to her house. Now for every event we had gone to together before that, I had brought a condom - just hoping that night would be the night. After hooking up for a pretty decent time, she looks up and asks if I want to bang. Problem is, I had been so used to the non-sex zone, I left the condom at home.

About a week after the incident, though, Emily texts me and asks if I want to watch a movie. I had just been feeling a little under the weather that day, knew I was coming down with a fever, but figured I'd go for it anyway. We got through the opening credits of the movie before clothes came off. This time, we were both stone-cold sober, so when she asked for sex 30 min in, I knew this was my time to shine. I jump out of bed, run to my wallet and reach for the condom.

But once the condom got on, my member deflated like a month old balloon. Only then did I notice how sick I was becoming. I had broken out sweating and Emily had noticed that I was getting hot (I tried to turn her comment into a flirtatious one and went about business as usual). We tried getting it up at least three more times to no avail and wound up passing out.

Three days later, Emily texts me saying that she was sick. No idea what was wrong - doctors did tests and said it wasn't the flu, wasn't mono, or anything else that has flu/fever/mono symptoms. They even tested her for cancer. All she knew was she had a 103 + fever, was aching all over and had finals the next day. Me? I broke my fever the next night and felt fine. Emily failed her finals, was sick for a month and a half with an unknown ailment, and knew I had gotten her sick somehow.

As for me? I was left with the humiliation of inadequacy looming over me (which all of her/my friends know about), was never forgiven for the misery I put her though, and had a long-term sure thing vanish in thin air all because I forgot a condom and got a girl sicker than the plague.


Photo: claudio zaccherini/Shutterstock.