Here Are Your Worst Prom Hookup Failures

Once upon a time at this fair site, we ran a series of posts entitled Drunken Hookup Failure, chronicling sordid tales of young lust gone horribly awry. Today, we've decided to bring DHF back for a special prom-themed edition. Here now are some of our readers' very worst prom failures.

Andrew:

It's 2006, and my senior prom was coming up, and I had just recently broken up with my girlfriend of three years, and I was struggling to find a date. My mother makes a suggestion of her friend's daughter Maria, who was just getting out of rehab for her love of prescription medication and mixing it with alcohol.

My mother says that Maria is looking to hang out with people who are clean, and she was trying to stay away from the crowd that led to her current situation. We were going to an after party where there would be alcohol, but it was BYOB, and my friend said that he stole two bottles from his uncle's house for our group of six people to drink. I didn't think it was enough for anyone to go overboard, so I decided to take Maria. On the way to Prom, I am just trying to make friendly conversation, and all Maria can keep harping on is how she has a boyfriend and that she doesn't want anything to happen between us. I said that it wasn't my goal to get with her, that I just wanted us to go and have fun.

We get to the Prom, and Maria would barely dance with me, and kept saying that she had a boyfriend and didn't want him to get mad. So we kind of just sit there for the remainder of Prom, and at this point I am just looking forward to getting drunk at the after party and hanging out with my friends. In the limo back from prom, it turns out my friend who was supposed to bring the alcohol for the group was full of shit, and he had barely half of a bottle of Absolut Vodka.

I was so concerned about drinking that I lost track of Maria once we got to the after party. I kept thinking that I just need shot or two, and I could turn the night around and at least just have fun with my friends. I ask my friend where the bottle was—he said in his backpack in the other room. We go into the other room to get the bottle, and we find Maria having sex with this guy named Dan (who was the boyfriend of another girl that was at the party), and my friend's backpack was opened, and the empty bottle of vodka was lying on the floor.

Chaos ensues, and Dan's girlfriend is flipping out; Dan frantically tries to explain that he was about to get changed out of his tux, and he entered the room to find Maria chugging the bottle of vodka, and she basically jumped on him. Dan's girlfriend leaves to go to another party, and everything calms down. I spend the rest of the party sober and fall asleep on a pool table listening to the sounds of Dan and Maria having sex again in the other room.

Scott:

So I liked this girl my entire senior year of high school. I had no balls, and even less game to make my feelings known. My strategy, looking back now, was doomed from the start. I entered the friend zone. We worked together after school at the same shitty grocery store. After about five months of being a friend and not getting anywhere, Prom season was fast approaching. She just broke up with her boyfriend, and I provided a shoulder to cry on. We had mutual friends, and they were all going to Prom together. My buddy told me this was my best chance.

I tried my best to ask her out, but my lack of intestinal fortitude wouldn't allow it. No shit, I was on the phone with her one night, and she brought up Prom. Still not finding my balls even though she was doing her best to provide opportunities, she finally asked me. Holy shit, yes, let's do this!! So Prom night finally arrived. The three couples rented the shittiest limo that broke down on the way to Prom. No harm, we had one hotel room for the three couples with plenty of liquor. I had a duffel bag full of condoms (even though I didn't know how to use one). We arrived back to the hotel and all started drinking.

One of the couples got into a drunken fight, causing his date to leave. He was all fucked up in the bathroom when my date decided to go in to talk to him. What a sweetheart. They ended up hooking up in the bathroom. So there's two beds in the room; I was embarrassed, pissed, but too much of a pussy to do anything about it. I slept on the floor next to her and her new boyfriend (for the night), with the other couple sleeping in the other bed. She ended up getting sick, and he ended up leaving. The next morning, I took her home. She looked like death warmed over. As I am stopped in her driveway, she looked at me and had the nerve to say she had a really good night, and thanked me with a high-five. My friends had a good laugh. To this day, when one of them brings up high school, they all point, laugh, and scream, "On the floor in '94." I fucking hated high school.

Anonymous:

Senior year, I took a girl to the prom who was a sophomore that was cute, and I thought I had a good chance at hooking up with her. We make it to the after party, which is being hosted by a very wealthy girl in our class at her mansion, and there is a DJ, tons of food, and even security guards.

For the party, I decided to treat my date to a bottle of alcohol of her choice, and she chose Alize (?!). She was really excited about this bottle of fruity, semi-alcoholic syrup and thanked me constantly, so I thought that would seal the deal.

As I was making my way into the party, I had three things to carry in: my bottle of liquor (Crown Royal if anyone cares), her Alize, and my sleeping bag, as no one was allowed to drive home. I grab my bottle in my right hand, and for some reason think its best to grab the sleeping bag with my left hand and hold the Alize underneath my armpit. I make it about 10 steps before the Alize slips from my armpit area and crashes onto the floor into a million pieces. I stand there completely in disbelief at what just happened and dreading walking in having to tell my date.

I walk in and my date has a huge smile, expecting her Alize, and I have to tell her I dropped it and it is no longer. Her expression does a 180 to the point where seems to be sad, disappointed, and angry all at once. She wasn't happy with me the rest of the night, and I could barely look her in the eye, I felt so bad/embarrassed, so my night with her did not end the way I was planning.

PS: Word got around pretty quickly about what I did, considering there was a huge pile of broken glass and red syrup on the way into the party. Apparently the security guards were even clued in on it, evidenced by the fact that a buddy of mine walked into the party 10 minutes after I did, asked what happened, and the security guard said, "It was [my name] — he fucked up!"

Conor:

Junior year, I was a virgin, and my girlfriend and I had decided we were going to do the deed on Prom Night. Really original, I know. But whatever; I was excited, she seemed like she was excited, my buddy had already gotten his older sister to procure us booze—we were SET. So after the dance, we made our way, along with 20 other kids, to the after-party at our friend Kaitlyn's house.

Turns out that this was going to be one of those parties where the parents were going to stay up all night with us. You know, to make sure we weren't drinking or fucking. Ironically, those were my two goals for the night. I had a waterbottle full of watermelon-flavored vodka, balls full of jizz, it was Prom Night, and I was getting laid. I was on a mission from God.

As soon as we got there, though, we realized God might have a sense of humor. This was a ranch-style house. There was nowhere to go. Except... the basement. At some point around halfway through the water bottle, my girlfriend and I snuck downstairs to get it on. It was an unfinished basement, with utility shelves and moving boxes everywhere, but right in the middle of the room was a couch and a coffee table. As romantic a place as any.

I sat down, and we started ripping each other's clothes off as she straddled me. I threw my shirt across the room, pulled my shorts down, and put on a condom. I had some trouble getting it in — possible due to being 17 and knowing nothing about lubrication. Finally, I worked my way in - and just then, we heard the basement door open. My girlfriend leapt off me and ran to the far end of the basement to hide. I saw a pair of gym shoes, and being confident and carefree (read: drunk on flavored Smirnoff), I assumed it was one of the other kids at the party and decided it would be funnier to stay put. I grabbed her discarded bra to cover myself. As the shoes came down the stairs, I realized with horror that it was NOT one of the other kids, but Kaitlyn's mom.

"Oh my God...what are you doing!?" She gasped. I couldn't do anything but try to look innocent.

"Nothing?" I shrugged.

She went into another part of the basement before returning to the stairs and taking another look at me: shirtless, shorts around my ankles, half a dozen condoms strewn in various states of opened-ness on the coffee table, bra covering my junk, and most importantly - alone. Very, very alone.

She sent her husband down shortly after. My girlfriend hid a second time, but thankfully I was dressed by then.

"Time for breakfast," he said. I followed him up. Breakfast was very silent and very awkward. There were plenty of other kids around who weren't privy to what had just happened. Eventually, we sobered up and went home, without any further discussion. My girlfriend and I laughed about it, until I realized that I needed to return my rented tux...and I didn't have my shoes.

I called Kaitlyn, asked her to look for them, but who answered the door when I showed up? Kaitlyn's mom. And she obviously remembered my face.

I talked with Kaitlyn recently about that night... to this day, her mom still thinks "that kid" was in her basement on prom night, naked, surrounded by half-opened condoms... jerking off alone.

Erin:

I'd had a huge crush on a certain gentleman in our friend group—Andrew—since junior year. We'd been running into each other and flirting at parties for well over a year, but due to his shy-as-shit personality and my relative inexperience with boys, nothing ever transpired between the two of us. It was assumed among our friends that he and I would go to the prom together, but he totally dragged his feet on asking me, which almost led me to bring a hot junior from the baseball team I'd had my eye on before Andrew swooped in with the late invite.

Cut to the night of the prom: Given the classic "special night" clichés and the collective lack of game that existed between Andrew and myself, I knew that this evening would be a) our last chance to finally hook up, and b) a situation where I was likely going to have to be the one to make the move. I was pretty much a nervous wreck by the time everyone got to my parents' house to take pictures. I tried to play it cool and let the night take its course; we were both looking pretty fine in our attire, and the close dancing, playful grabs and knowing looks very clearly set the scene: It was totally on.

Enter: The after-prom party. One of my fellow cheerleaders was hosting an epic throwdown—about 70 people in total, with each guest bringing his or her own 30-rack and an assortment of hard liquor. Wanting to conquer my frayed nerves and jump through the closing window of opportunity with my date, I kept a steady stream of apple Smirnoff, Captain Morgan, and Bud Light to my face for the first hour or so of the party as a huge group of us started to play cards. I'd lost track of Andrew by about the third or fourth round of Kings, but continued drinking in anticipation of making the big move later.

Apparently, Andrew had a similar booze-filled agenda, because the next thing I knew, someone came running in from the backyard with the announcement: "Erin, your date's making a HUGE SCENE." I stumbled outside to find a belligerent, bloodied Andrew being helped into a waiting car in the driveway by a number of partygoers. As the hostess's sister drove him home, I was informed by witnessing revelers that a blackout-drunk Andrew inexplicably pulled an R. Kelly and swandived off the one-story back deck, bashing his face in on the ensuing fall.

I woke up the next morning (on the floor next to the aforementioned junior baseball player, both of us fully clothed and otherwise untouched) to a phone call from a confused Andrew asking what had happened the night before. We haven't spoken since. I guess I'll never know if it was just nerves or an elaborate exit strategy, but tales of our mutual failure are lovingly retold by one of my friends every single time the old crew gets back together around the holidays.

And now, the worst one of all...

Michael:

This happened my junior year of high school in 1998. I was trying my best to woo a girl that went to a school in a town next to mine. The girl was certainly above my caliber, she was a year older and gorgeous. But, she was a bit odd. Looking back, I think she just wasn't very bright, but as a hot, in-demand high school senior, she was probably seen as the high school equivalent of eccentric. I started hanging out with her. We did a couple of the teenage dates where you go to a house to watch movies, wait until the awkwardness subsides, and then you make out. I made little progress in the sexual arena beyond that. I didn't push it, because I had no game and I was far out matched in the looks department, so I was intimidated.

She agreed to go to prom with me. The night was boring, not just because prom is boring, but she's boring. She mostly talked about weird stuff like raising show rabbits when she was little and really, REALLY liking animals. I can't remember the caliber of my typical conversations with girls when I was in high school, but I know I was trying to top that. I barely paid attention to what she said. No matter, she was swept away with prom romance. We made out. Her affection for me was clearly increasing. Prom was working. I was optimistic this was going somewhere and I was going to see it through to the end.

Fast forward to the end of the night. We went to some parties and stayed out after the prom until 5 or maybe later. I had made this my goal, because she had mentioned that her parents both leave for work at around 5, so no one would be home when we got to her place. It's a rural area, and she lived in the country. We get to her place and, hooray, her parents are not home. This was my chance. She knew it, I knew it. I parked the car and my teenage adrenaline was firing on all cylinders. We made out in the car and I was confident I was getting laid, I just needed some courage. All night, she (apparently) had been telling me that her cat had just had a bunch of kittens. Then she tells me I have to come in and see them. There it was, my opening, my affirmation that this was happening. (Oh, sure girl, I'll play your game. I'll let you save your dignity by concealing your unabashed desires for me under the guise of kitten viewing. But, once we get inside, it's on).

Well, it turns out she did really want to show me these kittens. So fine, let's get this over with, and then it's on to the main event. The problem is, and I am not a cat expert, but apparently mother cats move their kittens around a lot after they're born, so we had to find them. The cat had moved them from the laundry room to the back porch. The porch had random teenage girl crap stacked all over it. This included a wadded up volleyball net, next to which the cat had the deposited her kittens and within which they had all become entangled, strangled, and died. Yep. Five dead kittens.

She flipped out. Just lost it like a war widow. This is probably the worst thing she could have imagined, and it happened. She began crying, a lot. She started to untangle them from the net, and I started to help, because what else am I supposed to do. The combination of disappointment and confusion left me in a bit of a haze. Now, I don't know where co-officiating an impromptu mass kitten funeral is on the pleasure spectrum of life experiences, but I am pretty sure it is on the extreme opposite end of getting laid. But that's how my night ended. I think I even gave a brief eulogy. Ok, I know I did. I can remember saying the words, "They were taken too soon," and she said through her tears, "way too soon." She cried the entire time. She hadn't stopped when I left. We never spoke of it again.


Drew Magary writes for Deadspin. He's also a correspondent for GQ. Follow him on Twitter @drewmagary and email him at drew@deadspin.com. You can also buy Drew's new Kindle Single, The Rover, through Amazon.

Image by David Saracino.

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