Welcome to Great Moments in Drunken Hookup Failure, where we showcase three heartwarming true stories of drunken love gone horribly awry. Off we go.
A few years ago, I was drinking at this bar with a guy I used to date, Jon, and a slew of his random friends. Work friends, church friends, roommates, school friends, everybody drinks at this bar. I don't know most of the people and no one there knows that we used to date.
Everyone is having a great time and I'm cautiously drinking with the expectation of driving home that night. Of course, Jon keeps buying me drinks, encouraging me not to worry about driving so late, I should just stay at his place. Okay. He's an attractive guy, I've been here before. It's game time. Now we're both drinking heavily.
His one roommate starts ferociously hitting on him. She talks nonstop to the group about his mom and how she thought they were dating and "OHMYGOD! Isn't that funny!? Who would think that?" Then Jon hits the wall and interrupts her by turning to me with drunken confessions. "We could have worked. I fucked this up. I loved you and I never told you. We could have been great." He won't stop. The whole group stops talking and listens to him. I'm still sober enough to know that this needs to end right now but too drunk to drive.
I get us out of the bar and we get back to his place and he's in love mode. In his head, he's all ready to go down on me and totally rockstar my life. In reality, he's a drunken, slurring mess. He tries to finger me and it's like an overeager dog trying to get a treat out of your hand. I try to let him down slowly, no sudden movements, suggesting we try again in the morning. He passes out mid conversation. I think I'm home free to just sleep it off and leave before his roommate wakes up to us in his bed.
I fall asleep and then wake up really cold in the middle of the night. I roll over to find Jon pissing on both the bed and me. Instant drill sergeant. "Jon! WAKE UP. Now! You're pissing on me." He wakes up and tries to go to the bathroom but starts to get off the lofted bed by crawling in between the bed and the wall/window. "Jon! Not there. Over here. By the steps." Meanwhile, I'm trying to get out of the puddle of pee and simultaneously warm up and dry off. He moves to the right area and starts to descend only to free fall off the bed.
Against the wall.
With his head.
I see him start to fall and try to scramble through the piss to save him or something and end up tits deep in the puddle staring down at him crumpled up on the floor. We're in serious fucking shit mode now. I'm immediately thinking he has a subdural hematoma, he's not going to wake up from this, I don't have any medical supplies to do anything, paramedics and his roommates are going to come in to the both of naked and covered in piss and I'm screaming at him as I'm flying off the bed. He moves around and looks up at me and says, "Thanks for sticking with me. You're a good one." He lives.
The next morning the roommate tells me she woke up to a big noise in the middle of the night and fake jokes about what an awesome pounding I must have had last night, wink wink.
I leave without my dignity and with my unwilling golden showers card and he doesn't remember a thing.
In junior year of college I was friends with this girl Stacie. Sometimes she would bring her friend Karen over to my place to hang out. Karen was short, cute, and a lesbian. Obviously there was no point in hitting on her. One weekend night a group of us, Karen included, were on our way to a bar. Stacie comes up, pulls me aside, and tells me that Karen likes me and wants to have sex the next weekend. Wait, what? A bicurious lesbian wants ME to fuck her. Holy shit! A once in a lifetime opportunity falls into my lap.
The next weekend rolls around and Stacie and I head over to a party where Karen was. We come in to see her ripping bong hits and taking shots. She's happy to see me and we start chatting. As I get drunk and high through the night I realize that even though everything is laid out for me, there is a huge amount of pressure on my shoulders to make this happen. I had to make sure I didn't fuck this up. Stacie then decides to leave early, leaving me with Karen.
Karen and I leave the party and we start stumbling to her dorm. My apartment wasn't an option since my room was tiny and I slept on a narrow futon. She mentioned earlier in the night that her roommate rarely slept there since she stayed at her boyfriend's a lot. Perfect. We get to her room and start going at it. As I put the condom on we hear some noise across the room and realize her roommate is there trying to sleep. Fuck. Because of this, she insisted on trying to stay as quiet as possible under the covers and to play corpse. The combination of that and the aforementioned pressure led to the huge failure of a limp dick. She then pretended to fall asleep. I rolled over and fell asleep literally facepalming.
The next morning I quietly put my clothes on and left. A couple of months later while waiting on the street to meet up with Stacie, Katie and her group of friends coincidentally walk up. She was a little too enthusiastic when she said hi to me. I met some of her friends before and I could tell from their faces they knew. We said goodbye and after that I never saw her again.
It's my first year at a West Coast university, and things are going well. Easy classes and new friends/booze, etc. Two of my new friends were Bill and his roommate Chad. One day Bill tells me he knows two smoking hot girls from his hometown that are still in high school and want to come party at college with us. So the girls come down for the weekend and we all meet up at Bill's dorm to chat, and play video games. I was pretty shy at this age so I didn't really make the best impression. But one of the girls, Becky, was crazy hot and I was really hoping something would transpire with her.
Another problem was that I didn't know the rules on who Bill was going for, or if his roommate Chad was going to be around all night. After we all get tired of playing video games Bill and Chad decide to take the girls out to eat, and me being the shy guy that I am decide not to be a 5th wheel. So I just go back to my place and eat alone like shy people do. About 2 hours later Bill, Chad and the 2 girls show up at my place and want to party.
So we start drinking and dancing to the latest songs by T.I., thoroughly impressing the girls. Also at the beginning of the night the girls made it clear that they were new to drinking. Being guys, we instinctively started daring them to do some shots. As a result they ended up drinking way too much too fast, and are smashed within 15 minutes. Now the party of 5 people is getting pretty crazy.
All of a sudden Samantha starts aggressively making out with Bill, which I was pretty impressed by, being shy and all. They are having a good ole time rolling around on the couch/floor dry humping and such, when Becky starts proclaiming her drunken love for me and requests that I make out with her on the floor immediately.
Becky and I are getting pretty hot and heavy and things are looking good for me (possible first hook up at college). Now Chad is new 5th wheel, and he douchily decides to get in on the action with Samantha and Bill. Chad ends up stealing Samantha away from Bill and makes out with her for a while as she didn't seem to care who she was kissing.
Meanwhile, Becky and I decide to go hook up in my bedroom. So we stumble upstairs and she's ready to go, as in she is verbally telling me to do her now. But at the same time I guess things didn't work out between Chad and Samantha downstairs. So being the douche that Chad is, he comes up to my room and tries to convince Becky to have a threesome.
Becky and I object and tell him to get the F out of my room, but he won't leave. In the process of his douchery, Becky announces that nothing is going to happen now, and immediately passes out on my bed.
Samantha then comes up to my room and tells us to get her friend downstairs because she wants to go back to Bill's dorm. So Chad and I try to carry her downstairs and Chad being the douche that he is, drops her and she ends up getting a very visible bruise, that I hear about at a later date.
Later in the night I figured out that the reason Chad came upstairs was because Samantha puked all over my floor. Chad ends up pulling a multitude of douche moves over our brief friendship. As for Becky, we never really connected again. Hands down the hottest girl I ever had a chance with, gah.
Never trust a Chad.