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

T Co:

I have lived with the same group of six guys for my 4 years here at the University that I currently attend, with the exception being my friend Terry. He is a year older than the rest of us, and moved out after he graduated last May and became a police officer for the city. He works the downtown bars on the weekend, checking IDs and dumb shit like that. He still went out with us when he got days off, until the fateful February evening that destroyed our friendship.

Terry was working that night, so the rest of my friends and I were at our favorite local bar, Harpo's. We were posted up in the corner, surveying the scene while sucking down dollar beers, just like every other Friday night. I decided to abandon the corner and set off on my own on the dance floor.

It was then when I spotted a beautiful girl I knew. Although I had only spoken to her a dozen times or so in the 2 years I had known her, it was common knowledge among my group of friends that I was very much into her. I wanted to go up and talk to her, but she was talking to her asshole boyfriend. He left with some of his friends, but I was still too big of a pussy to approach her, so I gave her a wink, she smiled back, and I tallied that as a small victory and left it at that. Soon thereafter, my friends and I were all kicked out for trying to steal pictures off the wall. Surprisingly, that impressed Sara.

As fate would have it, we ran into her and her friends at the local late-night Mexican joint. They were looking to keep the night going, so we offered our house as a destination for more drinking, and they were in. There ended up being a few dozen people at my house, and everybody was dancing, including me and Sara. After a few shots, I was shitfaced enough that I decided to go for it. We started making out, and seconds later we were taking part in some heavy petting in the middle of my living room. At this point in the night, the most difficult remaining obstacle would ostensibly be receiving the approbation of her best friend. The chick was actually all for it, so I thought that was the last roadblock stopping me from finally hooking up with Sara.

I took the lovely lady down to the basement into my room, locked the door, put on the Boyz II Men, etc. After we undressed one another, she took a condom out of her purse and instructed me to put it on. It was one of those generic quarter-machine condoms that you get out of a gas station bathroom. I took this opportunity to whisper something sweet softly into her ear: "I'm still pretty drunk, you might have to give me a little bit of head first." She was cool with it.

So there I was, getting my dick sucked by the girl of my dreams when I heard screaming in the other room, and someone yelled "THERE'S A FUCKIN COP HERE." I knew right away it was Terry. His weekend shifts ran from 3 p.m. to 3 a.m., and he would always come over to eat and hang out afterwards. Tonight was no different than any other night besides the fact that we had about 35 people over, about half of whom were underage, including Sara (20) and her friend (who cares). Sara expectedly freaked out and threw her clothes on. Everyone upstairs had already dispersed, and Terry made his way down to the basement to look for us, still in uniform.

Seeing that Sara was in my basement, he looked at me, laughing, and mouthed "HOLY SHIT." I nodded. Terry always fucked around and pretended to bust the guests we had over, and he did just that. He told them to come outside with him for a moment. Allowing Terry to proceed with his little joke, I stayed in the living room with Mike while he pretended to call in her information. I noticed that this joke was taking much longer than it usually does. I checked through the blinds again and witnessed the two of them making out outside of his car. Then the two of them got into his car and left together. Terry is seriously a dead ringer for Ryan Gosling, so as you can imagine he rakes in tons of ass. Not only did one of my best friends cockblock me, but he performed a robbery on me. My cop best friend robbed me. After that, I ate the rest of my chicken nachos and watched the end of Titanic on HBO-so still a pretty good night by my usual standards.


I moved about eight hours away from my girlfriend for graduate school. For the first few months of us being away we would try to meet up whenever we could in Cincinnati because it was halfway for both us.

After not seeing her for about six weeks I set up a lovely weekend in the Nasty Nati. The last time we met up, she was on her period and didn't give dome so I had gone probably two months without sex. Eight weeks with no sex was an extremely long drought for me at the time. Before I moved she was on the pill and I had been getting nearly every day. I was doing a lot of jacking off.

So I was excited to see my girl (Tanya) and excited to get laid.

We met at a hotel downtown and quickly went to a wine tasting festival. Then we went to dinner and hit up a bar. We got pretty drunk and were both getting very touchy. At about midnight, we rolled back and were both ready to bang.

As we approached the room, Tanya said, "You have a condom, right?" She had got off the pill because she hated what type of scientific womanly shit it did to her. Of course I didn't have a condom because I'm an idiot.

I was hammered and wanted to bone. Everybody knows hammered guys will go to great ridiculous lengths to get it in.

"Don't worry hun, there's a CVS right across the street," I replied.

I ran/jumped down about 15 flights of stairs because I thought it would be quicker than the elevator and sprinted to the CVS. It was closed. But there was a Walgreens across the street. Closed, too. This makes sense because it was midnight. But I was drunk and all rational thought was pushed away by my urge to have sex.

I asked a passing by bachelorette party if they had one and they laughed in my face.

I flagged down a cab and asked if the dude had a condom. No, he had given away his last one, but he'd drive me to a gas station.

At the center of downtown, you'd think there would be a closer gas station than 15 minutes away. Or maybe I got played by the cab driver, who drove me a to a gas station in the ghetto.

When we pulled in, there were a handful of young black men drinking 40s sitting on the hoods of parked cars. You couldn't walk into the gas station, you could only order through a barred window.

I was the only white person in a two mile radius I'm guessing. I got out of the cab wearing pressed jeans and a dress shirt, and walked to the line. Normally I would have been scared shitless, but I was in that getting-ass-nothing-else-matters zone. I was behind a man wearing half of his hair corn rows and the other half in an afroThe man said to the cashier, "Dawg, I just needs some Mags" –referring to Magnum condoms. The man even tipped the cashier which I found incredibly odd and nefarious at the time.

I was up next and said the to the cashier, "I also need some condoms, but I – heh – obviously don't need Magnums." The cashier stared at me like I was speaking gibberish. There was a crazy look in his eyes.

"Dawg, all we gots are Mags," he said gesturing at a board – probably six rows by six rows – with nothing but Magnum condom boxes on it. This was not your typical gas station, but it knew its customers.

I took my Magnums and jumped back into the cab. The cab driver thought all of this was hilarious, but still charged me $40. Oh, and he only took cash so I had to go to an ATM preventing my poor dick from any action for even longer.

After about 30 minutes of being gone I triumphantly ran up the hotel stairs and into my hotel room, holding my $47 condoms (ATM charge, cab fare, actual condoms) high in the air, huffing and puffing.

All I heard was snoring. My girlfriend was passed the fuck out. I went to bed soaking wet with sweat a defeated man.

We never had sex again. Tanya broke up with me a few weeks later after a spectacularly catastrophic Thanksgiving weekend that included me showing up to her family's Turkey Day get-together with an inch long scab from getting a beer can slammed into my forehead the night before.


The year was 2008, and I was about to begin my Junior year. My roommate, Dave, was moving back early because he was an Orientation Leader. I saw this as an opportunity to quit my shitty manual labor job a week early and go have some completely unadulterated fun. However, there was a glaring problem with this plan. Because we were in a fraternity, our house, and our room, was closed for orientation week (to prevent freshman drinking). Dave was put in a tiny single in a dorm for temporary housing. I really didn't have a place to stay, rather, each night I would wander throughout the dorm and find an empty room to pass out in (the returning students weren't allowed to move in until later, so only a few rooms on each hall were occupied with OL's). I was a vagabond for the week.

I meet up with Dave and we start doing some SERIOUS drinking. A bottle of Maker's gets polished off in a little under an hour, and we decide its bar time. While we wanted to hit on some freshman, we knew we couldn't roll up to the freshman dorms and try to party with them, without being those creepy older dudes, so we decided the next best thing – the bar notorious for underage drinking. We figured any smart freshman would have said goodbye to their parents, and then immediately would have obtained an ID/try their older sisters out (the college was in a large city where ID's are a must). We get to the bar, order LITs, and start drunkenly chatting up some girls. I hit it off with one chick, and we start sloppily making out in the back of the bar, to the disgust of pretty much everyone. After an hour or so of this (and a few more LITs) she says she wants to go back to my place (the freshman didn't want to be "that girl" the first day at college, she had a roommate). We leave and get back to my place where I realize my grave error. In my drunken stupor, I had led us back to the locked frat. Being a brownstone, there was a nice little vestibule at the entrance so we make out some more.

Then sunlight. All the booze must have caught up with me because I blacked out hard. I was alone, in the vestibule, with my pants around my knees. In my drunken stupor, I managed to pass out mid hookup. She left me there, half-naked, to fend off the bums and homeless people that regularly hang out on our stoop.