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


This happened a few summers ago, a local dive bar was closing that year in our city, and every Thursday night everyone you knew would go and get hammered. This was the type of place where drinks were cheap, spaces were tight and there was lots of sweaty action on the dance floor.

This hot girl was into a rich friend of mine, who could never seal the deal. I told him I would play wingman, trying to set him up, while setting myself up for hot girl's friend.

The bar closes and I go with the two girls to my friends house to use his hot tub. I'm pretty wasted at this point off beer, as I can't stand the taste of hard alcohol.

All four of us get in the hot tub and I'm pretty drunk, I start complimenting the girls on their beautiful bodies and they seem to be pretty receptive. We're pairing off and things are going great in our two corners of the hot tub. One of the girls starts drinking some alcohol in a water bottle and offers me a sip.

Not wanting to seem like a pussy, I oblige. When the stuff hits my lips, it was some really warm rum, and because I am such a pussy that can't drink hard alcohol my gag reflex goes. I can't hold it in and puke the nights worth of beer in the hot tub.

Obviously everyone stops what they are doing and leaves the hot tub. The girls drive me home on the drive of shame. I am pretty upset because I ruined things for me, my friend, and his hot tub.

My friend didn't have the balls to tell his strict family that someone puked in his hot tub so he just poured some additional chemicals in, and let nature take its course.

Once in a while I get messages on Facebook from the girls laughing about the incident.


So me and this chick Heather (we'll call her my wife) are at a swanky, high end steak house thanks to the $150 gift certificate I won in my office Halloween contest for having the best costume (Lloyd Christmas for the win!) and we are having a great time. The drinks are flowing and we are having good conversations about various stuffs and things. As the night wears on and Heather is getting more intoxicated and starts talking about how we are going to get crazy naked-style when we get home.

We are finishing up our meal and I start to notice her ‘drunken lazy eye of intoxication' tell she gets right before happy horny Heather turns into grumpy, tired, leave me alone Heather. I have her drink a bunch of water and pay the check as fast as possible. As we are walking out to the car, I haven't lost her to the dark side yet, and she is still expressing interest in getting buck wild when we get home. On the drive home she is kissing my neck, grabbing my junk and whispering drunken slurs into my ear (with rancid breath that I ignore because I feel she is teetering on the edge of becoming grumpy Heather). 20 minutes later we arrive at home and start to get down to business.

She interjects and says that she wants to take a shower before we have at each other and off she goes. For some reason it doesn't initially click that I should have taken a shower with her, but after about 7-10 minutes it finally does and I go into the bathroom. What do I find? She is sitting in the shower against the back wall with the water hitting her in the chest, completely passed out. I start nudging her to wake up and all I get is, "I'm up, I'm up!" in her grumpy Heather voice. Knowing the night is a loss, I play with her passed-out titties for a couple seconds, go into the computer room, jack it, then get her out of the shower and put her to bed. In the morning she feels bad she fell asleep on me so I got a half-assed beej and complete breakfast of Cheerios made for me. Married life is grand!



Saturday I'm at some stupid themed frat party (the theme was twins) when Abby and I start making out and petting and she tells me she wants me to come back to her apartment, and there's no question in my mind I'm getting lucky that night.

We were safely back in her friend Mary's apartment when, within two minutes Abby gets a text from her ex and runs out into the living room sobbing. She continues bawling her eyes for the next hour while lying on the living room floor, only taking breaks to go into the bathroom and puke. Naturally, as the roommate and best friend, this entire episode requires Mary's attention, while I sit there awkwardly, not ready to give up on the night but not wanting to linger too long and seem like a creep. Abby finally makes her own bed, with Mary's assistance, and I think I might finally be back in the clear. However, after sitting there for about ten more minutes waiting for someone to come out, and with each passing minute wondering more and more if it was time to go, Mary finally comes back out with some bad news. "She's still going in there and is gonna be pissed if I leave... you can stay if you want, but I know from experience its gonna go on for awhile."

Finally defeated, I left the apartment and called my friend for a ride back, who, thinking I was still inside and not outside in a t-shirt (it was November in the northeast) with a dead phone, finished cooking and eating his late night snack before getting around to helping me out. Looking back on it, I woulda thought she was using her roommate as an excuse after changing her mind, but friends of mine who know her better than I do confirmed that sobbing and puking and demanding attention was a favorite weekend activity of Abby's.

The worst part of it was, in my confusion over the situation, and with the subconscious fear that my phone would instantly die if I so much as took it out of my pocket, I never asked for her number, and thus was never able to initiate anything until too much momentum had died off by the next time I saw her to just pick up where we had left off. Didn't help my cause that she ended up hooking up with our star basketball player (a lottery pick that year) a few weeks later and turned into a genuine jersey chaser. Nevertheless, I still hit on her every chance I could the rest of the year, and this year when I go back to visit, failing to ever again get past casual flirting.