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Illustration for article titled Cockblocked By Your Own Psyche!

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


So I was hanging out on a boat with a bunch of people and started flirting with this one chick. We ended up hooking up a little bit, and then heading back towards the lake house we were at. We go inside and everything is looking awesome: Clothes are coming off, and she's starting to grab my dick. She sucks my dick a bit, and then I decide to go for the full thing, and start taking her swimsuit off so we can fuck. And I also start to finger her a bit. It didn't take too long before I realized that my finger was covered in period blood. She freaks out and runs off, I assume to do whatever girls do when they have a period. Needless to say, that was the end of that hookup. So, I got cockblocked by TOM (time of the month) which is not that unusual. What I think IS unusual is that this was a fucking dream. I got cockblocked in my own dream. Essentially, where literally fucking everything is possible and should be awesome for me, I cockblocked myself. Fuck me. I was so confused and pissed off when I woke up.


God, dreams are the worst.

Jack W.:

Several years ago, I was in the first semester of my "victory lap" year at a small state school in west Tennessee. I had graduated in four years and during that time had been heavily involved in freshman orientation activities. My involvement in these activities also allowed me to work in close proximity to the admissions/recruitment staff. The woman who was second in command with the admissions department, Stephanie, had been an object of lust amongst most of the males on campus.

My roommate during this magical 5th year was two years older than me and was employed as one of three junior admissions counselors. We had plenty of spare time on our hands, so we would frequent the one or two local bars virtually every night of the week. He would always call Stephanie and invite her to come along, and sometimes, she would join us. I had known here casually for four years at this point, so I had no reservations in veraciously hitting on her.

One night, the three of us were at a local bar, and I picked up where I had left off the previous night with the sexual advances and overt flirtation. Several beers and shots later, we moved to an even shittier bar where things continued to escalate. We started to make out, and I pulled my friend aside and told him to get the hell out there. He and Melanie had both driven, and I was simply improving my odds of a trip back to her house. We stuck around for a few minutes later, before I convinced her to leave. Sadly, she was not willing to go to her house, a detail that is still very strange to me. Instead, she drove me back to my house that sat at the end of a dead end street. She parallel parked her shitty Toyota Camay in front of my house, and we continued to make out while her car idled. Things start to get heated and she pulled my shirt off before climbing into the passenger seat with me. Soon, I had the seat reclined, and the hot, unobtainable assistant admissions director was blowing me…well.

I leaned back and enjoyed this victory for all male students. In my euphoric haze, I suddenly got the sensation that I was moving. I attributed this to the magically fellatio and tried to put it out of my mind, but I quickly found that I could not. In her haste to jump me, she had apparently hit the gear shift with her knee, dislodging it into neutral. We were rolling forward towards the end of the street that happened to dip before rising again into the embankment of the train tracks that ran through the middle of town. When I noticed this, I couldn't help but laugh. If indeed, I was about to meet my demise, this was going to be glorious. I tapped her on her head and said, "We are moving, madam." She looked up in a panic and tried to grab the gearshift. I continued to laugh. "Pull the emergency brake," she screamed. In my inebriated state, I couldn't find the brake in this unfamiliar car. Instead, I just continued to laugh. The car rolled over the end of the street, through some shrubs, through a ditch and came to a rest wedged into the train track embankment. I opened the door and fell out into an old lady's lawn laughing hysterically. Stephanie was not pleased.




In January, I took a new job with a Double-A baseball franchise in the South. This required me to move to a new (and very small) city. Not knowing anybody, and having to work 75-hour weeks during the season, made it nearly impossible to find a new girlfriend.

A few months into the season, I met this girl who worked for us on game nights. She is very, very cute, sweet, and smart—by far, the best I have met in this place. We went on a few dates before she went home for the summer (in a different time zone) and agreed to pick things back up when she came back in the fall.

We kept in touch throughout the summer and started hanging out again when she got back. We had only made out so far, but I was finally getting her to warm up to the idea of letting me sleep with her.

After going to a movie one night, we met up with some friends at one of the two bars in the city. She always seemed to get friskier whenever my credit card was out, so I threw it on the table and told her to order as much as she wanted to drink. After quite a few drinks, she leans over and whispers that she's ready to jump on the Highway to Happy Town. I grab her hand and knock over several people as we sprint back to my truck for the ride to my apartment.

As we take off, she starts looking through her phone (whatever, she's a girl...girls have to be on their phones). She gets real quiet for a few minutes, so I ask her if everything is ok. IT IS NOT. She had just received a text message from her mom that said (nearly direct quote), "So, we just gave away your dog that you've had for the past nine years because we didn't want to take care of it anymore when you aren't home. Sorry."

After that, she was sad, and nothing I could say got her to turn that vertical frown upside-down.


What kind of mom texts that to her kid? MONSTER.


This happened to me in the summer of 2005, about 3 months after I graduated from college. Three of my friends and myself decide on a random Tuesday night to go to this local shithole college bar, which is known exclusively for Tuesday nights and 50 cent drafts of Natty Ice. Basically this place was such a shithole it had to have its promotion night be a fucking Tuesday so people would actually go. It's not actually half bad on this night, I get my 4 dollars worth of Natty Ice courage in me, and have my eyes set on the little blonde Spanish chick. As luck would have it, I'm outside smoking a cigarette and the blonde chick, Nikki, comes up to me and asks to borrow a smoke. This is a no-brainer, and next thing I know she's telling me her life story, how she broke up with her boyfriend THAT NIGHT before coming out, and asks me to head to the dance floor.

Next thing I know I'm out on this tiny 4x8 excuse of a dance floor making out with Nikki in front of a table that turns out to be her friends. Instead of being a Cockblock Coalition they are actually interested in the 3 other guys I'm with. Mind you, this Nikki is about 10x hotter and 1/4 the size of the other girls, but this matters not to my friends. All is well for the next hour or so when we all get the invite back to their house. We get the address and agree to meet them, no problem. When we pull up and walk to the front porch of their place, we are greeted with screaming from inside the house. Turns out Nikki's boyfriend was waiting for her when they got back, and they are in a full blown argument. I figure my chances are shot, night is over, nothing to see here folks. But right as I'm about to give the night up for dead, Nikki opens the front door and tells her now ex-boyfriend to leave, and as he walks out sees me and 3 other guys. He understandably gets even more pissed, pleads to Nikki, "I know if I leave you're just gonna fuck one of these dudes!", who isn't hearing it. He walks away sheepishly after 5 more minutes of pathetic pleading.

With this fiasco out of mind, I figure that the last of my roadblocks with Nikki have been removed. My friends and hers are now sitting around and drinking shots of tequila and god knows what else when Nikki asks me to go back to her room. Bingo! My hard work and perseverance have paid off. We get in the room and not 5 minutes have gone bye before the clothes are off and I'm downtown, when I hear a knock on the door.

I figure it's a drunken roommate and proceed back to work. Next thing I know, the fucking door IMPLODES and her fucking boyfriend is there in a rage. I'm completely naked, hard as a rock, and I'm using his girlfriend's thighs as earmuffs. I stand up, and am more scared at the thought of having to fight this kid completely naked than having to fight in general. He looks at her and says, "I can't believe you would do this to me! I never did anything to you!", then looks me up and down and says, "Have a good night man", and walks out. My mind is completely blown, but when he walks out of the doorway, I can clearly see 2 of my friends WATCHING THE ENTIRE FUCKING THING. The fucking douchebags friends of mine saw the enraged boyfriend walk in, and proceded to tell him what room we were in! Needless to say I didn't score with Nikki that night and my entire roster of wingmen would have to be restructured.


I've said it before and I'll say it again: Friends are awful.


I was in downtown Santa Barbara at a club with some of my buddies. We buy several rounds of tequila shots to commemorate our last downtown trip together as we are graduating in less than a week. We walk towards the dance floor and I spot her immediately. Cute Asian girl with freckles. She's dancing with a guy so I bide my time.

My friends and I exchange a few more rounds and I'm back on the dance floor. Now some other tool is lording over her. At this point, I'm pretty loaded so without thinking, I walk up to her, ignoring the tool, and chat it up. I'm guessing she found my assertiveness attractive because there's no way I'm spitting any resemblance of game at this point.

We eventually make it to the dance floor where we essentially shag with our clothes on in front of dozens of people. I get tired so I drag her to the back of the club and start getting more physical. We were definitely going to bone that night. This will be the easiest hook up ever! But right when I thought I had sealed the deal, a fight breaks out two feet away from us. They scuffle and tackle each other, eventually bowling us over. Freckles hits the deck with a bloody nose. People jump in to break up the fight. Once I get my bearings straight, she was gone. While everyone was reeling from the fight, I walk around aimlessly through the club to find this chick, but she was nowhere to be found.


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