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


So around 3am we leave and she agrees to come back to my house….by this point I'm beyond drunk. We get to my bedroom and start going at it. It hits me halfway through our make-out session that it's gonna be a struggle to get it up due to extreme whisky-dick, but I continue to dry hump while I remove her clothes. So we finally get to the point of no clothes, and she whispers the magic words, "Do you have a condom?"….So I scramble though the drawer in my nightstand and finally find one. I go to slide in missionary style….I start thrusting, and it my drunken haze, it feels like I'm inside her. Then the following conversation happens after about 30 seconds;

Her – "Are you gonna put it in?"

Me – "I am in."

Her – "No…you're not"

Me – "Yes I am"

Her – "Seriously….no you're not."

I glance down and notice that I'm not inside her….I had been humping the bedsheets between her legs. The mixture of condom lube, sweat, and extreme intoxication made me think it was her vag. By this point she's just disgusted, so she says we should stop….I tried pleading that I could do it, but to no avail. I passed out a short time later and never hooked up with her again.

"You got a shoehorn?"


We're making out and I get her bra off. I touch her breast and it's the silkiest, smoothest mound of pleasure I've ever felt in my life. Her long blonde hair is flowing over her breasts and she's straddling me. At the time, I didn't have a lot of experience and I couldn't control myself. Her breast in my hand and gorgeous face caused me to cum prematurely. After I came, I kept making out with her hoping I could weather the storm and be ready again soon. We change positions and she sticks her hand down my boxers before I could stop her. I'll never forget the disgusted, disappointed look on her face. She laughed a little bit and I apologized under my breath.

She puts her shirt back on and then gets a call on her cell phone. She frantically tells me it's her boyfriend and I have to "get the fuck out or he will beat my ass." I already came in my pants and now I'm about to shit my pants. She apologizes and tries to tell me how they broke up, but it's complicated…blah, blah, blah. She gives me her phone number and tells me to call her.

I call her every 3 days for two weeks and she never calls me back. I try one more time and she answers. I ask if I can get a chance to redeem myself, but she tells me that it's not a good idea because she's pregnant with the guy who was going to beat my ass if he found me with her.

I told my friends the same story, but told them that we had mad, passionate sex and then her boyfriend called.

That's a fair reason to lie.


We're completely naked and I'm pleasuring her with my hands, she's going completely crazy, when all of a sudden I hear a big bang. I look over and the girl in the heat of the moment smashed her head into the light switch next to her bed. She was out cold. What was I to do? Using my better judgment, I threw on my clothes on and got the hell out of there.

THAT is your better judgment? What's your worse judgment: shooting her?


I'd wanted to hook up with Shannon for quite a while and one drunk evening during fall semester it seemed as though everything was going my way.

When we got to her place there was a note on her door from her buzzkill friend who'd just had an abortion that day. Shannon said she had to go talk to the girl but would be right back. In the mean time I could make myself at home with her refrigerator full of beer and her new CD player. CD's were still relatively rare back in '87 and this was literally the first time I had seen one outside of a high-end electronics store. So I settled in with some beers, some Elvis Costello, some English Beat, and the certain knowledge that I would be hooking up with Shannon. So happy. So tired.

The cruel light of day found me sprawled on Shannon's living room floor, surrounded by dead soldiers and CD cases. She said that when she got home she tried multiple times to wake me up, but I wouldn't budge, so she just went to bed. Not surprisingly, I never got another shot at her again.

Oof, the dreaded abortion cockblock.


I go to Temple University and every spring we have a day called "spring fling". This is basically a day where there are tons of booths around campus selling things or hosting games. In other words everyone gets drunk as shit and makes a fool of themselves.

Anyway, I was texting the girl that I was hooking up with at the time and we decided we would meet up later that night. We literally never hung out unless we were hooking up, so it was implied that "meet up" meant "have sex".

So around 8 at night we go to my friend Luke's house where he's grilling burgers and boom, I get the text "hey come over"

So I make my way over to her place, but we end up going to my room and the hook up begins. I was, for lack of a better term, wasted and I ask her if I should get a condom and she agrees, yes it is time to have intercourse.

I attempt to put the condom on my penis and I quickly realize that putting on a condom when you can't see straight is maybe one of the most difficult tasks ever. Seriously, that should be an Olympic event, drink 15 beers, try to get hard, then try to put on a condom. If anyone can do the last two things in under 15 minutes, they deserve a medal and a parade. Well my attempts to put on said condom result in the condom only covering the top half of my dick, that's the only way I can describe it.

However, both of us agree, fuck it, we're gonna have sex regardless of the condom situation. instead of taking off the condom, we just decide to leave it on for whatever reason. Well we start effing and at one point I slip out and I look down, and the condom is just gone. And instead of just playing it cool and not saying anything I just freak out. She doesn't seem too worried about it, and I try to explain that the only place my penis went after I put on the condom, was her vagina. Therefore, the condom, is more than likely, in her vagina.

Long story short, she goes to the bathroom, comes out and goes, "I should leave". Clearly, she figured out where that condom was while she was in the bathroom. She never told me she found it, but you don't just leave mid sex unless some shit happened, such as finding a used condom in your vagina.

You missed a golden opportunity to pull that condom out of a top hat. MAGIC!


Shortly after I got married, my wife and I decided we were gonna do something different. We had talked about anal sex, but she wasn't sure she could do it. So we decided that we would try anal beads first. If you don't know what anal beads are, they are just beads that come in different sizes that are on a string with a tab on the end that goes on your finger so that they don't get lost inside of the person. Anyway, she decides on the medium size beads and there are like 9 beads on the string. So, one night after a few drinks, we head upstairs and decide to try them out. I gently slip the first one in. She flinches a little. I slip a second one in, then a third, then a fourth. She's like, "Ok, ok, no more." I, of course slip one more in. "Fuck! No more! Take them out NOW!" Now, I didn't realize that I was supposed to take them out gently, and by the way she's freaking out, I figure I need to hurry, so I pull hard and they come out with a very loud scream. My wife is pissed. She turns to me and screams, "What the fuck do you think you doing, pull starting a fucking lawnmower!" We have not even spoke of anything anal-related in the 5 years since.

Can't imagine why.