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


I was recently visiting my buddy Jeff in DC for 4th of July weekend. I have been interning in NYC all summer and although it's been a great time, the ladies haven't been paying me too much attention. To say that I was in a sexual dryspell at the time would be a heinous understatement. Jeff introduced me to some his friends, including a girl named Melissa who also had a friend in town that weekend who we'll call Laura. We were hanging out all day, watched the fireworks together and I bought her a bunch of drinks that night.

We get back to Jeff's apartment and within seconds we were making out and her top came off. The first sight of her chesticles made it apparent that my long hiatus was well worth the wait. I began to creep my fingers down her side and started to unzip her pants. I was centimeters from the holiest of holies when she suddenly grabbed my hand and the night took a terrible turn down shit-street. Here is how it went down:

Laura: "I don't think you should go down there."

Me: "What, are you on your period?"

Laura: "Not exactly."

Me: Very confused and scared face. "Then…. what is it?"

Laura: "Well I have something inside me that girls in Africa get to prevent getting raped, and if you stuck anything in there it would hurt you really badly."

Me: (Blank stare.)

Feeling like an asshole for trying to get with a girl who has apparently been sexually assaulted before and not really knowing what to say, I just laid there in bed until I passed out. The next morning, still perplexed by the happenings of the night, I asked Jeff's roommate Carter if he knew anything about this contraption and he informed me that it is called a Rape-aXe. He said that it essentially is a vaginal sheath that has barbs on the inside of it that snag onto a guy's dick when he tries to pull out which is excruciatingly painful and that it can only be removed surgically.

Although I was still upset that I missed out on getting with a hot girl, I felt a little better because I managed to avoid getting my dick mutilated by her vaginal dentata. This sentiment did not last long however because a week later, Laura's friend Melissa, having caught wind of what Jeff and his buddies were now calling the "Guillo-vagin", dismissed the story and was adamant that Laura had a Rape-aXe free vagina and that she gets with guys all the time.

I think celibacy might be my only choice now that I am at the point that girls are making up fictional Rape-aXe's just so they don't have to get with me.

Oof. I understand the need for RapeaXe, but it's a flawed vagina trap that forces the rapist to remain inside you until help arrives. Do you really want your angry rapist hanging around there any longer than is necessary? It should just cut the penis clean off so that you can get away from him quickly and easily.

Broken Shoelace:

My friend Sarah (not her real name) was a bartender at my favorite bar. I would drink unlimited rail G&Ts all night and pay $5 at the end of the night as long as I tipped her nicely. So this one night I was getting drunk. Sarah's friend Lucy comes in to the bar and starts chatting up Sarah. I guess Lucy was being annoying, so Sarah told her "Go talk to Bill (not my real name), you know he wants you. You need to hook up with someone tonight." It was quiet enough and Sarah was loud enough that I heard her say it. Lucy was already drunk enough that she actually came over to me. I had made it known a few months back that I thought she was really hot. Lucy was beautiful. I had known her since freshman year. I never had a chance until this night for whatever reason.

We start chatting. We took a shot of something or other. Probably a woo-woo, but who knows. I didn't need it that was for sure. Lucy starting hinting at the time I had let it be known I was into her. I helped her along and basically just told her I'd love to go home with her. She was game. Her roommate was leaving soon so we hitched a ride with her (it was like 1am on a Friday so the roommate MUST have been drunk, but that's neither here nor there). We get back to Lucy's place. Her bedroom is a typical girl's room. Big fluffy pillows. Feather bed. Really comfy. Smelled nice. A great place to hook up. We start making out on her bed. My shoes, shirt and jeans come off. I get her shirt off so she's in her bra, but she excuses herself to the bathroom after that to "change". Ok whatever, i'm thinking. It's still gonna happen. She's totally into me. No problem here. I wasn't sure if it was just gonna be third base or if more was going to happen, but I was going to be happy with just her bra off. She had a wonderful pair.

Oh right, but I'm drunk. I used to chug these huge G&Ts all night back then. So gross. She's in the bathroom and i'm in my boxers on the bed sort of fiddling with my little guy. You know, I'm aiming to impress. I get it in my head that I should surprise her with my wang out when she comes out of the bathroom. I take him out through the fly on the boxers. Full mast.

So she comes out of the bathroom in her bra and some little shorts and sees me and it. She is immediately repulsed. Fuck. Fuck. Fuck. This was not a good idea at all. My drunken playfullness is now coming across as rapey-aggressive or something. Fuck. So she basically walks over to the bed and tells me to leave. I'm drunk so I dont even have my thoughts together enough to put up a fight. I put my clothes back on and start to tie my shoe. I pulled too hard and broke a shoelace. For the next year or so, whenever I put on those shoes with the short lace, I thought back to that night and how stupid I was. PLAY IT COOL NEXT TIME IDIOT.


Ah, the dreaded Roethlisberger Technique. Never works.


First night (actually afternoon) of college, I ended up getting drunk with my new roommate immediately after our parents leave. We are pretty toasted when our RA shows up telling us we have to go to some useless orientation event. We are well and truly drunk by this point but make our way down while the RA gives us a load of crap. The event is a joke, a bunch of speeches and useless welcomes. I notice a good looking young coed sitting by herself a few rows up. I move up a few rows, sit down next to her and start in with my drunken high school "game". For some unknown reason, this is actually successful. She invites me back to her car ("my parents are in my room"). We are just getting down to business when my parents call, where was I we were supposed to meet for dinner? I throw every excuse I can while she is actively giving me head. I mention we need to hurry up and we proceed to have sex with her on top of me in the backseat, no condom. She gives me her phone number, and I head back to meet my parents wreaking of sex and whiskey with an idiot grin on my face. Dinner was uncomfortable. I called the girl the next day, disconnected phone...seriously WTF. Never find her again.

Fast forward to my bachelor party years later. Low key event, the groom's party, brother-in-law to be, and my father. Towards the end of the night, we end up at the hotel bar, its me and one of the groomsmen, we'll call Dani. Yes I had a girl on my side. We're hammered and trading hookup stories. Dani had always been 'one of the guys'. I start telling her the above story and she looks utterly ashen, and then starts to cry. I, stunned, try and find out what's going on. She proceeds to tell me that SHE was the girl I hooked up with in the car. She said she was truly bummed I never called. OHHHH...it all drops into place now. I hadn't been able to call her because she had gotten a new cell phone when she moved to school, but gave me the old number. Damn, opportunity missed there.

Further, she had ended up with an ectopic pregnancy (don't look up images of that). Had emergency surgery, almost died, and had to drop out of her first year and start over. When she came back, she had gained about 25 lbs, cut and dyed her hair and looked totally different. I met Dani through my wife, they became friends at orientation the next fall. So I had just found out that I had unknowingly hooked up with one of my groomsmen, and nearly killed her in the process, the day before the wedding. The wedding went off without a hitch but man did it feel awkward. My wife still doesn't know and we all hang out regularly.


Sounds healthy.


My friend "Chuck" and I are in Texas on business. We each have our own hotel room but they're in different hotels a couple of blocks away from each other.

We go to a bar one night and meet two very good-looking girls. The redhead is into Chuck, the blonde is into me. This is phenomenal. The only problem is that I'm drunk out of my mind, and as many can attest to, that can be a blessing and a curse. In this case, a hell of a curse.

The blonde girl offers to drive us all to Chuck's hotel, but first we stop at Taco Bell. The other three get Mountain Dew and maybe a quesadilla, but not me. I eat a huge, huge fourth meal of greasy, disgusting fast food. We continue on.

We then go back to Chuck's hotel. While the girls are in the bathroom doing whatever chicks do, Chuck and I come up with a plan. I'm going to ask the blonde to drive me back to my hotel room. That way, Chuck and the redhead are alone, and the blonde and I are alone after I invite her up and she surely accepts. Also, just asking for a ride won't force us to address the obvious elephant in the room—that we all want to fuck—because many girls don't want to admit that out loud.

The girls like the idea. They want this as bad as we do, and they appreciate our subtle idea to set this up without declaring that we're all whores.

So I climb in the passenger seat of the blonde's car, the plan is working amazingly, when I start to feel it. The stomach is gurgling. Bad. The Taco Bell passed right through my system and now it's demanding its release. Now.

I have to take a dump so bad that it's taking undivided concentration just to keep my ass sealed. And the obvious question surfaces. Do I invite this blonde up to my room, then excuse myself and take a massive (and probably loud) shit while she's sitting on the bed waiting for me?

I couldn't do it. I was in such agony that when we pulled up at my hotel, I politely said "Thank you for the ride. Have a lovely night" and gave her a kiss on the cheek. The blonde, dumbfounded, gave a forced smile and says "Oh, OK" before driving off.

What's worse, the blonde girl then immediately drove back over to Chuck's hotel, banged on the door and told her redhead friend that it was time to go home (they were at 3rd base by this point). So my drunkenly ravaged bowels cockblocked not only me, but my buddy too.

The dump, however, didn't disappoint. It was every bit as violent and noisy as I anticipated. There was no way the blonde could've come up to the hotel room and not been mortified at what would've undoubtedly transpired. The way I see it, I had no choice.

Naturally, neither of us ever saw those girls again.