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

Dumb Nice Guy:

At the start of my junior year in college, my friends and I were living off-campus. A friend of my roommate who lived near our pad was throwing a Halloween party. I was particularly looking forward to it because the hostess was the best friend of a girl I had met and the end of my sophomore year named Sara. The first time I met Sara, I had a jolt of an instant connection to her that I had never felt before (or since). I was convinced that I was going to marry her (I even played a frenzied game of Blades of Steel against a buddy for the exclusive rights to try to date her). I knew Sara would be at the party, so I was ready to get to know her better and sweep her off her feet. My pathetic plan as a "nice guy" involved inviting her over to my apartment for a dessert treat called Brownie Bottom Pie. I was convinced that she'd be blown away with me and we'd live happily ever-after.

My friends and I arrived fairly early at the party. On the way in, I recognized a freshman girl from the campus named Hannah who happened to be the roommate of the hostess's sister. She was dressed as a very attractive leopard in a skin-tight outfit. Something about seeing her and her vibe towards me made me think "uh oh." But undeterred, I found the keg and started to liberally consume its contents. After a while (and many beers for me), Sara arrived. The good news was she somehow looked amazing despite being dressed as a witch (complete with the green skin). The bad news was that she was being a responsible designated driver for her friends. I figured I could overcome this development, and we started to hang out together. She was into me, and everything seemed to be proceeding according to plan.

Then Hannah started to come over to me and pull me away from Sara for various reasons. First it was to take a whack at a piñata. Next it was to participate in some drinking game. Each time she pulled me away, I managed to escape and make my way back to Sara, who was not happy with Hannah. The next time Hannah pulled me away to dance, something short-circuited in me. I had never had two girls fighting over me before, and I had no idea how to handle it (especially while being drunk). I wound up dancing with the sexy leopard, which caused Sara to seethe. The next thing I knew, Sara was leaving to drive her friends home, and I realized that I had messed up. But, there was nothing else to do but invite Hannah back to my apartment to have the Brownie Bottom Pie dessert that I had made for Sara. She was happy to go with me, and I drunkenly figured that I could salvage the night.

After flirting over my brownies, hot fudge, and ice cream concoction, I made my move. As I went to kiss her, she stopped me cold by announcing that she had a boyfriend back home. I processed this unwelcome information, and asked "are you sure?" She confirmed it, and I mumbled something about not wanting someone to do that to me if the roles were reversed. We killed some time, and eventually she wound up sleeping over our apartment on a pullout couch while I went upstairs to my own bed. The next morning, I had to drive her back to the hostess's apartment. I assume Sara found out that her nemesis Hannah had left with me AND slept over, so she assumed some sort of hooking up had gone down. I never really had a chance with Sara after that despite my best efforts. I will always wonder what would have happened with Sara if not for that sexy leopard who happened to already have a man....


Earlier in the summer, friends from college were getting married in the Northeast. As such, alot of people I know and am friendly with from college attend. The group of us were all staying at a nearby hotel, which was separate from the reception and ceremony. One of the people in the group of friends is a girl we'll call Amy. We weren't really too friendly in college, but we had hung out in groups before, and we had been friendly and flirty, but nothing beyond that.

Fast forward to the reception: we had an open bar, which led to me having entirely too many whiskey and sodas. Anyway, Amy and I are sitting at the same table and we're hitting it off. We're talking at the bar, dancing (poorly), etc, etc.

The reception ends and we head back to the hotel. By then its only 12:30 or so, so the group decides to go back to our respective rooms, regroup and then meet at the bar. I'm sharing a room with my buddy, his girlfriend and another friend. My buddy decides to crash with his girlfriend, and the other friend decides to stay in too. I remain undeterred, knowing Amy and her friends will be there.

We all meet at the hotel bar, and we continue talking/flirting. Her friends are playing with the juke box and talking to other guys, and slowly leave and go back to the room they are all sharing. This is where it gets hazy. We make out obnoxiously at the bar, and upon her request to leave, we do the same in the hallway back to her room. Great, things are going well. We get back to her room and she's invites me in. I drunkenly accept, and this is where things go black. Nothing happens (as far as I know) because the roommates were there, and we go to bed.

Well, next thing I know, I wake up, lying down in the hallway at 7AM, and I immediately know what happened. I slept-walked right out of the room in the middle of the night. It's something I rarely do, but happens every once in a when I am particularly drunk, and based on conversations and personal witnessing, it's something my brother and cousins also do.

So, all I have on is my pants, an undershirt and socks.The only thing in my pockets is my room key, and I am not sure I am outside Amy's room, so I walk back to mine. Across the entire hotel. I received judge-filled stares from nearly every hotel staff and non-generate hotel guest I encountered. I get back, stumble in the room, pass out there, and a couple hours later have to make the unfortunate call to their room (my buddy remembered their room number) to ask "Uhh, do you have the rest of my suit, shoes, wallet and cell phone?", which thankfully she did not dispose of. Amy apparently thought I just ditched her in the middle of the night, in such a rush that I couldn't bother to grab all my stuff. I explain and she's less mad, but the damage is done. Awesome.

I then later in the day get a message from her that she still has one of my cufflinks. I have yet to get back said cufflink.



I recently traveled to San Diego for a weekend trip to visit a buddy from high school. Heavy drinking was on the agenda, as was going to the Chiefs-Chargers game (Those $100 tickets sure looked great after KC started 0-2) So it's Saturday night and my buddy has a few friends over, we grill, drink and decide to head out to a club in downtown San Diego. We stop at some Irish pub for a quick beer before the club, where my friend orders a Guinness ... and bread pudding. Fast forward to 30 min later, we're in line about to go into the club when my friend complains of an upset stomach (probably because he just consumed 2,000 calories of bread pudding).

So he takes off, leaving me with four of his friends (two couples, no less) to enjoy the night. We make it in, dance, drink, dance and drink some more. Around 1:30, they all decide to hit the bar for one more drink. I finish dancing with some girl and head up to the third floor bar to find them, only to get denied by a bouncer because it was apparently too late in the night to go to that floor. So I'm on the second floor, clueless where these people are and with no phone numbers. I start texting my friend, trying to get numbers when I'm approached by an attractive blonde who says her friend thinks I'm sexy. The friend, a very good looking brunette wearing a low-cut white dress, then sheepishly walks over. We make small talk and end up on the dance floor, where white dress girl (I think Brittany was her name) and I proceed to bump and grind all over each other. Suddenly, she's at the bar, talking with blondie. Brittany doesn't return to the dance floor so I casually go ask what's up. She then tells me that the two are lesbians and blondie is getting jealous of our dancing. Blondie then grabs Brittany's hand and storms off, leaving me hanging.

I then meet up with two of the four friends outside, telling them the story when the lesbos walk out and head the opposite direction from me. Figuring what the hell, I catch up and ask if there's room for one more in bed on this night. I glance at Brittany who smiles and starts nodding when blondie perks up. "I like pussy, not dick," she snaps. Left me with a major case of blue balls. And the closest to a threesome I'll probably ever get. Woke up with a massive hangover the next morning, drank even more at the game only to see the Matt Cassel gift-wrap a win for San Diego on the final possession.