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


So it's late in high school and by unfortunate turns of events I am still a virgin. I had been going back and forth between two girls all year but had yet to seal the deal with either. They both knew about this and hated each other, yet for some reason would still talk to me. So the first girl, Jane, I figure I have a better chance with, and so one night at a party I find myself alone with her in the basement. After lots of making out I ask her if she wants to have sex.

She starts hysterically crying and whining about how I'll go back to the other girl, Jill. Mid crying rant I get a call from my friends upstairs saying there's a better party going on. I leave her in tears on the couch, jump in the car, and immediately call Jill. She says she wants to hang out later so I figure I'll drink some more then find my way over to her somehow. Suddenly, Jane shows up at the party, and tells me she wants to have sex later that night. I can hardly control my excitement, and the appointed hour comes around and we go to my car, a shitty small sedan.

We're in the back seat while our phones are in the passenger's seat. It's cramped, I have no idea what I'm doing, I'm struggling to get the condom on, I can tell she's getting frustrated and then a phone rings. She checks to see if it's her parents, but it's Jill calling. Jane then goes through my texts, sees everything from the whole night, gets out of the car and doesn't say a word. I sit there naked with a condom on my flaccid penis incredulous at what happened. I ended up not moving and falling asleep in my car in a deep state of depression.



It was my first year of grad school at a large public university in Indiana. I went to a popular bar on campus one night wearing a T-shirt with the logo of another large public university from my home state a few states away. Thanks to that shirt, I took up a conversation with a nice-looking young lady with a huge rack - let's call her "Anne" - who was an alum of my home state university and happened to live in town. She was with a cockblocking friend, so we didn't get anywhere that night, aside from introductions, as we didn't get to talk for that long. However, about a month or two later I ran into her again... this time we were both a bit more drunk, and she was obviously quite happy to see me. One thing led to another; we started making out at the bar, and she demanded she enter her number into my phone so I could save it. (The thought of calling her phone, at that point, was clearly too easy for either of us to figure out.)

Here's where the DHF started. I had just gotten a new phone that week and hadn't entered any new numbers yet that weren't still there from my old phone, and apparently when you type in a number on this phone, you are presented with two options to save the contact: "Done" and "Cancel." In my drunken state, reading which one was which was not an option, so I incorrectly assumed that the "Done" was on the left. Bad idea. She may have entered that number, but it sure didn't save. The problem was I was way too drunk to notice this little fact.

Eventually, she asked me to walk her home and I figured I was in for sure. We were upstairs in the bar, so we had to walk down to go out. When we got downstairs, she wanted water, so I walked with her on my arm to the bar to get some from the bartender. It took literally two seconds to get the water, but when I turned around she disappeared. I ran out the door to the bar with water in hand, to no avail. No freaking clue where she went. This is when the shitty new phone thing started to rear its ugly head. I looked in my phone under "Anne" and saw nothing. I probably called a few people in the As at that point, waking them up I'm sure as it was 3 a.m. at this point. Did a thorough (or as thorough as can be given how drunk I was) search of the existing contacts hoping for a typo, but it was not to be. I stumbled home and passed out, never seeing her again - well, that's not entirely true. Thanks to my incredible creeping skills, I did manage to find her on Facebook despite only knowing a first name... but she denied my friend request.



So a few week ago I meet up with this chick, we'll call her Katie. Katie's really really really into my roommate James but he, having a girlfriend, shows no interest in her. Naturally she begins to gravitate towards me, being that I'm James' roommate and by getting with me she think it'll make him jealous or something. So long story short Katie throws herself at me and we and up banging. End of story, right?

Turns out Katie feels really bad about us hooking up, like she betrayed James or something, which is complete crap since he doesn't give a shit about her. She spends the week sending texts to him, which he pretty much ignores. She also sends me Facebook messages, which I respond to, saying that she should hit me up if I'm out next weekend.

So that brings us to this past Thursday. I end up going out with another of my roommates, Barry, and a few other friends. We get blazed as fuck (like to the point that I'm struggling to control myself....I hadn't smoked in like 5 months), and then head to a Mexican restaurant where we proceed to get shitfaced of margaritas. After that, we head to a bar close to my apartment where my rugby coach is the manager. It's like 2:30 by this point so the place is pretty empty when we walk in, but who should come up to me but Katie.

We talk a little, and she says she got separated from her friends and needs a ride home, aka she's all over me. Being the gentleman I am, I offer that my friends will give me and Barry a ride home, and then drop her at her apartment, which is nearby. We go to my place first and she seems crushed that I'm gonna leave, but in my current state I feel like I don't wanna make shit awkward, so I say "goodnight" to my friends and let them take her to her place. Dumb, I know. The second that I get back into my apartment, I text Katie asking if she wants to come over and "hang out or watch a movie". She seems up to it, but wants me to pick her up.

It's important at this point to mention that this girl is Asian, and that I've been known to have a thing for Asians in the past. James and Barry are still up while I'm trying to meet up with her, and naturally start giving me shit. Anyways I rush out, pick her up and get her back to my place. Again she's a little awkward to come back cuz of James, but I eventually get her inside under the premise of "watching" Superbad. We go into my room to get to my laptop and Katie, going into my room first, sees my computer open to a full screen video of hardcorn asian porn.

While I was picking her up, my roommates, being the assholes that they are, had gone to some kinky ass asian porn website. I quickly hurry to shut it off, but the moment is clearly lost. We go back to the car and talk for a while and bs, with me trying to get her back into the mood, but in the end it's a loss. We end up having some hardcore make-out/heavy petting stuff, but nothing more, and sadly I'm forced to drop her back at her place with enormous blue balls and return home to the hardcorn asian porn.

The lesson here: Don't give your roommates time to fuck shit up for you.