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Crappiest One-Night Stand Contest: The Winners

Wow. We knew, when we asked you guys for your tales of terrible one night stands, that we were going to see some seriously messed up shit, but you managed to surprise even our jaded, Chlamydia-ridden eyes. Below are the entries that fulfilled the admittedly narrow qualifications of both making us laugh out loud and not getting us arrested if we printed them (last names have been removed to, in some small way, preserve the dignity of all those involved). To the winners: Our congratulations and commiserations in equal measure. We hope you use your brand new Motorola ATRIX 4G Smartphones for slightly more noble pursuits (although we know you won’t).

I was 21 and in a bar trying to enjoy my last night before going on that plane trip to boot camp. I was on my fourth beer when the hottest looking woman came and sat next to me. We talked and drank for an hour and I told her my sob story about having to go into the military the next day: She was all comfort and concern and invited me to her hotel room. I felt it was my duty to go and that night was one of the best nights of my life. I left before she woke up with a note saying thank you (I felt I had to be polite). I got to boot camp and lined up with everyone else - I was feeling pretty proud of myself until I saw who the Drill Sgt was for the women. None other than my "too hot too handle but I handled it anyway" one night stand. She stared me in the eye and every part of my body shrank minute by minute. Now I know why they call them drill sgts - they have drill eyes that drill right through their bodies!

Yikes. We didn’t think there was a level beyond “Holy crap I just slept with my future employer”, but Arnie, old buddy, you found it. Ouch and ouch again.

I hate to admit it, but I was drunk (or dumb) enough to let my girlfriend follow this ex-hockey player to his house for a one night stand. She slept on the couch while we were having a great time. Afterwards, his pet Rottweiler came in and started licking my toes. Next thing I know, the dog is humping me and the guy is passed out drunk. I ran through the house naked, screaming for my friend, while the Rottweiler chased me and jumped on me again to hump me. She starts dying of laughter while I'm naked and stuck under the dog, then the guy wakes up to find me. To top it off, I had to explain the black eye and cuts! How do you do that?

Sheryl, you are clearly what is known in the Maxim office as “Dog Bait”. It is both an honor and a burden.

My crappiest one night stand was when I was 23. I met a girl at the bar and brought her home to my parent’ house. After she went down on me, I noticed something sticky all over myself… Turns out, chicky forgot to take her gum out first. I spent the next 20 minutes cutting wintergreen gum outta my pubes.

Thanks for ruining gum for us forever. And pubes.

I met this hot guy at a party, things were going so smooth! We had a few more drinks, got a bit tipsy, and then decided to get a room for the night. Once back at the room we had a few more drinks and were laughing having a great time, then... it was suddenly morning. I had passed out! I looked around and I was all alone in the room! I went to check out only to be told the credit card the guy had on file was declined and I was stuck paying the bill. What a crappy AND expensive hangover!

Always remember to run a full credit check on a one night stand, kids.

I was 22 years old and hadn’t lost my virginity yet. I was talking to this lady on a chat program and she lived close by, so I decided that was my chance to finally lose it. I drove over to find that she lived in a beat-up trailer park, and when she answered the door she looked more like 45 than 33. She undressed me and lay me down on top of her bed that was covered in clothes (dirty or clean, I don’t know, but lumpy as hell to lay on) then got on top. Being my first time I popped after about 30 seconds but it went on for much longer - she just kept going! After she finally finished, I returned home feeling a bit more like a man… until I went to change and realized I was covered in blood. And that was the time I lost my virginity in a one night stand to a trailer park woman on her period.

The story itself is bad, but what makes this entry so special for us is that last line, which sounds like a deleted scene from the unrated edition of Forrest Gump. Go on, read it in Gump’s voice: “And that was the time I lost my virginity in a one night stand to a trailer park woman on her period. And that’s all I have to say about that.” It’s been cracking us up for a week now.


My crappiest one night stand went as follows: The woman I had this one night stand with, we met on Twitter. We talked a few times and exchanged the obligatory sext messages. We both finally were able to agree upon a place and time to meet. Once in the hotel room, she nearly squeezed the life out of me by clinching her thighs together with my head between them! Afterwards, we decided to go get some dinner, but later, as we’re making out again, I started to get an upset stomach. I was able to get it calmed down, but then proceeded to get a bloody nose. I started thinking these were signs, but tried to ignore them. We relaxed in the bed for a little bit, making out a little, then both of us grabbed our phones and started going through the routine of checking Facebook, Twitter, and emails. Upon checking my Twitter account, I discover a tweet SHE just sent out stating exactly, "I am in my own living hell.” I tried to will myself on, but it wasn't possible. Needless to say, I'll be more cautious on woman selection for future one night stands!

Holy God, that’s awful. Welcome to the 21st century, where there are a whole new set of ways you can be humiliated after sex!

I had a one night stand that I thought went pretty well, but in the morning she shot at me five times with a small handgun. If it gets any crappier than that, let me know.

Honestly, we don’t even care if this one was made up – the complete lack of any explanatory details just made it even funnier.

My tragic fail started out at a barbecue. There was way too much alcohol flowing, and not enough food. A lot of us were playing drinking games and I got really drunk, way too early. I decided to hit on this smoking hot babe who seemed like she was ready for a cover shoot in Maxim. Oww! After some pretty heavy flirting, I asked if she had a place we could go to and she said yeah. Next thing I remember, I wake up in bright daylight, in a room that look eerily familiar, to screams and pounding on the door. Uh oh, was I in a nightmare? I would soon find out: The chick I thought I'd picked up was my Aunt's niece, Jennifer, who was visiting from out of town! She was staying there because our Aunt was in Vegas. I was too drunk to notice the house we were going into the night before. Luckily, she said I passed out on the bed before anything could happen, but our whole family was thinking the worst. People were screaming and pounding on all doors of the house. Every phone was ringing... her cell, my cell, the house phone. It was CRAZY! We could hear her dad, my mom, and other relatives outside yelling at the top of their lungs, “Marco STOP, she's your cousin!!” “INCEST!!!” “Jennifer, open this door NOW!!” “Should we call the police?” “Break it down!” We stood horrified and frozen together inside not knowing what to do. Then miraculously, she told me to hide in a crawl space in the bedroom while she went to answer the door. They stormed in demanding to know where I was and she said I wasn't there. They accused her of lying because someone said they saw us leave together, and she laughed and said that she hadn't been feeling well and yes, I took her home, but I left right away. They checked the house as I held my breath - luckily, they didn't find me. To make it look even more legit, she went out with them for breakfast, leaving me in the "mean-hangover-with-no-means-of-escape-crawl-space." The thing was so hot, pitch black, loaded with blankets and pillows and what seemed like a thousand stuffed animals. I don't know how long I was in there, but I fell asleep and when I woke up, I escaped through the bedroom window and told my family that I slept at a buddy's house. I haven't seen Jennifer since, and I am so glad to say, I survived... the crappiest-one-night stand EVER!

Wow. Just…wow. We’re going to go out on a limb and say we “believe” you that nothing really happened, but still, the image of waking up in bed, bleary-eyed and confused, next to your cousin, while your mom hammers on the door screaming “Incest!” made us cry tears of pure, schadenfreude-y joy. Congratulations, sir – you are both a winner and a quite spectacular loser at the same time.