GREAT MOMENTS IN DRUNKEN HOOKUP FAILURE: The Saddest Hookup In the World

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

We have lots of sad stories here every week, but I'm afraid Peter's is the saddest of all:

I married my high school sweetheart and that was my first mistake. We tied the knot at 20 after our sophomore year in college. Yes, I had forgone all casual high school and college sex to marry this woman. Six years later I found myself overweight, depressed, broke, and freshly separated. She left me for a professor in her master's program. At that point, I was pretty desperate, because I had only been with one woman my entire life and I was terrified it would remain that way. I transformed from a once respectable young professional into a sad creature with a bit of a Vicodin problem whose sole power was to make single women uncomfortable at work. I actually developed a friendship with a coworker who shook off my advances and saw me as a decent guy who had fallen on hard times. While she was completely unwilling to fuck me, she was perfectly okay with setting me up on a date with her recently divorced, single-mother-of-two stepsister.

I met my date at a local restaurant that I can only describe as a slight step up from Western Sizzlin'. I discovered my coworker's step sister was perfectly Midwestern; she was plain, very kind, and exceedingly boring. Our conversation progressed from awkward to amicable as we both went through cocktails, and at some point close to dessert, it became apparent that we were two people drinking ourselves to the point where we could stand fucking each other. I invited her back to my shitty apartment and she consented.

I hadn't been in my apartment for several days, because the air conditioning was broken and the maintenance crew was taking their sweet time to fix it. I was staying with my parents in the meantime and I certainly wasn't going to bed my date nary ten feet away from where my mother slept. As soon as I unlocked the door to my apartment, she pushed me to the couch while slobbering on my neck. She really enjoyed sucking on my nipple, which honestly made me feel like I was being molested. But about ten minutes into it, she started blowing me and between booze, painkillers, and adequate blowjob, I felt incredibly content. I had the standard marriage where the blowjob was a rare event, and between that and the months of sexual frustration, my toes began to curl and I realized I was about to disappoint my date. And just I was having the realization, I began to hear an unsettling, but all too familiar sound coming from outside my door. It was the sound of someone shuffling through their keys. I twitched to warn my date, but the door swung open and I found myself starring at a short, portly Hispanic man in overalls. Days earlier, I had told this man that I didn't care what time of day he came by to fix my air conditioning, because I wasn't staying there. I guess he liked to work evenings. I felt any number of overwhelming sensations in the following seconds, but the one that persevered was the feeling of wetness on my chin. I quickly gathered that my date had stopped blowing me, and somewhere in the excitement, I came on my face. The maintenance man stood there for what felt like an eternity. My date looked up at me and we shared a really unfortunate moment. It was probably the only time we had connected on a personal level all evening. She threw her clothes and left. I thought about trying to convince her to stay, but I remembered I just had cum dangling from my chin, and decided it was best to let the evening end.

I called in sick the next two weeks and found another job. I went on living with the paranoia (or certainty?) that everyone in the apartment complex had heard about the incident. I didn't renew my lease the next year.

Oh, that is so sad. It's like an episode of "Louie," but somehow even sadder.

Sarah:

My husband was a second year law student. It was the week before final exams and he had been spending nearly every second of the day and night holed up in the library studying—-a grueling regimen that required large quantities of caffeine and Adderall.

One night, he came home cracked out and stressed out. In an effort to help him unwind, I ordered him to disrobe and lie on the bed. I climbed on top and begin kissing his chest, slowly working my way down to the promised land. A few sucks in, I noticed that things didn't smell quite fresh down there. I opened my eyes and quickly saw the source, a little dingleberry that had nestled in his taint hair. I kid you not, this thing looked like a miniature chocolate egg perfectly placed in the bed of a pubic Easter basket. I immediately started laughing and fell off the bed into a hysterical ball. In between cackles I managed to blurt out, "P-p-p-p-poo. Poo. Poo. You have poop." My poor husband bolted out of bed like a cat on the 4th of July and sprinted to the shower.

Afterwards he sheepishly apologized and explained that the caffeine and Adderall had a laxative effect (as any user of "academic enhancing drugs" can attest to) and that he had ruined the library with a messy dump earlier that day. I still tease him about it.

As well you should.

Rynocerous:

My friend introduced me to Stephanie at the bar, and we had some pleasant conversation. However, she quickly left to talk to other friends, and I didn't talk to her again for much of the night. She seemed to know everyone at the bar, and was constantly flirting with guys, dancing, taking pictures, etc. I didn't mind, because I was happy to get out and have a couple of drinks, and I wasn't really expecting to hook up in any event. By closing time, it was apparent that - as you might expect of a girl celebrating her 28th birthday - Stephanie was much too drunk to drive herself home. I figured she would get a ride from her cousin, or her gay best friend, or one of the myriad men she danced with at the bar. Much to my surprise, however, she asked me to drive her home. I agreed, but even at this point, I wasn't expecting a hook up - we had barely spoken at all.

As we sat in her parking lot, I went in for a friendly hug goodbye. She had other ideas, however, and she went in for the kiss. We made out in the car for a few minutes, then quickly moved the party inside her apartment. After some foreplay on her couch, she asked me if I wanted to "have fun." I assumed (correctly, in fact) that that was her euphemism for sex. I told her I didn't have any condoms, because, again, when I left my apartment for the night I was not expecting to hook up with anyone. Thankfully, however, she had condoms in her bathroom, and we proceeded to "have fun" on her couch.

While I wouldn't consider myself grotesquely fat, I have certainly never been described as an Adonis. I think a good adjective for my body type is "doughy." So, needless to say, the fact that I was hooking up with a hot woman (especially considering she initiated everything) was quite exciting. It was just the confidence boost I needed after being dumped.

Back to the story: Stephanie and I are on her couch, Cowgirl-style. Then, in the middle of the action and completely out of the blue, she reaches down, grabs my love handles with both hands, and says "PFOOOSH."

(I've spent a considerable amount of time trying to think of a way to describe the sound she made. The best I've been able to come up with is this: you know when a child is playing with toys, and they crash the toys into each other and make a sound trying to simulate an explosion? That was the sound Stephanie made as she grabbed my paunch.)

I was completely taken aback and laid there stunned for a few seconds. I tried to get back in the saddle but quickly realized that I had no desire whatsoever to continue having sex that night. I left her apartment and went home a dejected man. Needless to say, the experience was not the confidence booster I was hoping for.

At least she didn't give you a raspberry. WHO'S GOT SUCH A CUTE LITTLE BELLY? IT'S YOU! YES IT IS!!!

David:

I moved from the east coast out to San Francisco a few years after college, a year or so after that, one of my best female friends from school moved out west as well to Napa. Now for the better part of my college career, I had a huge crush on this girl though we had always been strictly "just friends". Throughout college she always had a serious boyfriend and frankly, in comparison to most of my college hook-ups, she was considerably out of my league.

So after I heard she's moving into the area and invite her to my birthday party. At this point, she had just moved to California and didn't know a soul. I, on the other hand, had met quite a few solid friends and had pretty damn awesome birthday party in the works.

As soon as she arrives at the party it was pretty much on, she's all over me pretty much from the get-go. I'm introducing her to all sorts of fun people, we're taking shots, telling old stories, yadda yadda. Next thing you know we're outside the bar making-out full force and decide to cab it back to the hotel where she was staying in downtown.

We get back to the hotel and start making out on the bed. We're both getting super into it. I get her shirt off but she initially she won't budge on the pants, this goes on for what had to have been at least 45 minutes when finally she's super worked up and says those golden words, "Get a condom".

My head is spinning, I've dreamed about this precise moment for the past 6 years and it's finally gonna happen. I get the condom on while she takes off her pants and is laying in front of my totally nude. It's about to go down…

Then all the sudden… I start losing erection. She's grabbing it trying to guide it in but it's refusing. We literally tried everything – attempted to wedge it using my pointer fingers as a splint, get it going "myself" while distracting her by making out, she tried to revive it her hands and mouth. We're both getting very frustrated at this point. It went from half limp, to mostly limp, to totally limp in a matter of a minute.

Eventually she got upset/annoying with the situation, rolled over and went to sleep. I attempted to get it going the next morning but she had zero interest.

She moved back to the east coast a couple months later and I haven't seen her since.

So simple, yet so horrible. "You got a shoehorn?"

B:

At my college, the first week back from winter break always turned into a huge party week—nearly a spring break atmosphere. It was my senior year and that week all of my friends and I had been going out to the bars around campus. This particular night, it seemed like we were all ready for a different level of drunken debauchery. I'm at one bar, becoming incredibly intoxicated, not worrying about the classes I am already falling behind in, when this unbelievably hot girl that I had never seen before starts talking to me. Admittedly, I'm not the best looking guy, and my game is average at best, so I'm a little thrown off, but things seem to be going ok. More drinks start going down and I'm really feeling like this is going well and we will surely be copulating later that night.

The bar closes, and she's getting a ride back to her apartment from a friend, and asks me to go back with her. I easily oblige and know this thing is in the bag. We're driving what seems like forever to this girls apartment, and a tidal wave of urine fills up my bladder. I'm holding this impending river of piss and we finally get there and she's fumbling with her keys and what not, so I think, fuck it, I'm pissing outside. Mind you, I'm borderline blackout so I start to relieve myself and something feels off. I realize that my dick is caught on my jeans somehow and I'm pissing straight down my pant leg. This is not a little dribble, but one entire leg is soaked in urine. This girl is waiting for me inside and I have just pissed myself. It's dead of winter at my school in a rural town in New England. There's snow on the ground so I get the brilliant idea that I'll just wipe myself completely down in snow and say that I fell in.

I go inside, and immediately I can tell she's not buying this at all. I take off my pants because "ohhh I'm so wet I just fell in the snow!". Everything is going downhill so fast. I make a move to get into bed with her because she is heading that way and I'm denied flat. She gives me this napkin of a blanket, tell me to sleep on the couch, and shuts the door. I'm thinking, fuck that, I'm out of here. So I steal a hoody from her closet—it's freezing outside—and decide to trek it back to my place that is closer to campus. I know it's far, but don't truly know. The apartments at my college are spread out in all areas away from campus. Within 10 minutes of walking, I'm completely lost. Service on my nearly dead phone is brutal, I'm in a fucking farm town. Every one of my roomates and friends is passed out drunk at this time, which is about 4:15 AM, and I'm getting hypothermia, and my piss soaked jeans aren't helping. The next 2 and a half hours I spend walking/running/doing jumping jacks to avoid death, and finally make it to my apartment complex somehow. Turns out, her apartment was five and a half miles away from mine. I never talk to this girl again, but share some awkward glances with her walking through campus.