Welcome to Great Moments in Drunken Hookup Failure, where we showcase four heartwarming true stories of drunken love gone horribly awry. Off we go.
Junior year in college, I was semi-together with a girl who we'll call "Jen." During this time when we were semi-together, a preseason basketball game took place on campus in honor of something that I don't remember/isn't important. The game was between the Phoenix Suns and the Denver Nuggets, so naturally everyone was all star-struck because professional athletes were on campus. Anyway, one night my friends and I are out at our favorite bar, as are Jen and her friends. Not long after we get there, in walk JR Smith and Dahntay Jones.
After bugging the living shit out of JR Smith for a solid 20 minutes (because everyone knows he could be a superstar, he's just too cool to try), I go back to whatever dumb shit I was doing and carry on with my night. I do notice, however, that Jen has struck up conversation with Smith over in the corner. I feel very torn about this-on the one hand, this is supposed to be the girl that I'm taking home tonight, but on the other, this is my chance to become Eskimo brothers with JR Smith…
Before I have a chance to make up my mind, JR and Jen disappear. Her friends and I are trying to find her when someone comes in and goes, "Jen just got into a limo with JR Smith, you may want to track her down." I walk about 30 feet before one of Jen's friends finds me and tells me that Jen is crying outside of Smith's hotel because she's afraid of the size of his dick. I reluctantly go with them to get her, thinking at least I'll get laid tonight even if JR doesn't. Wrong.
I can't help but make an obnoxious comment to Jen. Needless to say she was not happy and stormed off to go home, a solid 2 miles from my apartment. About an hour later I got a text from her saying that she wanted me to come over and was sorry for getting upset, because I was such a good guy for coming to "save" her. Unfortunately I was hammered, my car was blocked in, and 2 miles is quite a distance to walk when you're drunk.
So to recap: JR Smith doesn't get laid, I don't become Eskimo brothers with JR Smith, and I don't get laid. Fail.
Like J.R., you just weren't willing to put in the effort.
Friday night during my first year at a crappy Catholic college in the Northeast. Around Thanksgiving, I'm randomly invited into my suitemate Juan's room. He was setting up a beer pong game with himself and two lovely ladies and they needed a fourth person. Naturally, I join without a moment's hesitation.
Juan and one of the girls, Nikki, are celebrating getting As on a biology exam. Juan had helped Nikki study and she seemed very appreciative. During the first game Juan casually mentions he feels he deserves a blowjob for his tutoring efforts. Nikki turns him down but while laughing and Juan senses he has an opening here. I'm also trying to pass my (awful game) on her friend Stacy, and feel alright about myself so far.
We keep playing pong and getting drunker and drunker, Juan is pursuing this blowjob hard but Nikki is resisting, albeit never shutting him down for good. We keep playing and finally call it quits when we can barely stand. I bring Stacy into my room and bed, but after some drunken making out, she is not down for going any further and leaves to head back to her room. I pass out soon after.
Roughly a few hours later, I'm woken up by a bloodcurdling scream. Since I'm drunk and disoriented I fall back asleep soon after without thinking much about it.
The next day, I run into Juan and notice he is doped up. I ask how his night went with Nikki. Turns out after a few more hours of begging, Nikki gave in and gave him head, only Juan was so drunk after all the drinking that he fell asleep in the middle of it. Nikki got so mad that she actually bit the shit out of his dick and punched him in the balls a few times. Juan was at Campus Health for half a day for pain pills and making sure he could still have kids.
Moral of the story, stay the fuck awake during head. Should be obvious right?
It sure should.
The story goes back roughly five years, as I was maybe a year out of college, still living at home on Long Island with my parents. Weekends, I'd come into the city, hang out with friends and crash on a buddy's couch and trek back to the island the next day.
This night, my friend decided he wanted to go to bed early, and I had to decide if I wanted to crash on his couch or head home to LI early. Cue Lisa, who graduated college with us who I used to have a thing for her in college. Lisa and her friends were still out and we thought we might meet up. We were texting while I was en route to Penn Station as tried to make the early train – I did not. Next train was two hours later at 3:50. I texted Lisa to see what she was doing. She was headed back to her apt on Lexington, in the upper 20s and I could come over (10-15 min walk to her place from Penn station).
I head to her place, drunk and hopeful. I turn the corner to where I roughly know she lives (never been, just knew cross streets). As I get close, there is a suspicious looking gentleman standing on the corner who gives me a weird look. I say suspicious not based on his race, but because he was standing on a random corner after 2 am just hanging out by himself – I think nothing of it.
I text Lisa, "on your block where do u live" – no response, I try calling, and calling again, and probably sending another text. Now I am getting pissed, slightly worried, and confused as I had just texted with her – why no response? Then it starts raining as I am standing on the sidewalk. I decide to cross the street and stand under an awning to stay dry and continue to try to reach her – at this point, I just want to go to bed as probably it's around 3 am, I'm drunk and tired, and now a bit wet because of the rain.
Next thing I know, that same suspicious looking gentleman is standing 10 feet away from me, and says "hey, you wanna hang out." I respond with, "Nah, man, I'm good." He informs me that he "lives right over here" and points to a doorway right to a building right behind him. I continue to decline his advances to get better acquainted. His response, "I'll suck your dick for free."
I turned, and ran, as fast as I could, in the rain. I got to the next corner and was happy that I was not being chased – not that he would but I was drunk and terrified. I was unable to get a cab and walked/jogged the rest of the way to Penn Station in the rain. I arrived home to my parents' house close to 5am very angry at what transpired (at least I made my transfer at Jamaica).
The next morning Lisa called me apologetic, saying she either got sick or passed out, I don't remember. We're still friends but we never hooked up.
YOU COULD HAVE HAD A FREE BLOWJOB YOU FOOL!
I was dating a girl in college named Michele. One night my friends and I were up to our usual debauchery when I get a text from Michele that says she's on her way over and the sole purpose of her visit is sexcapades. That text is the last thing I remember.
I woke up the next morning naked in bed, the sheets were completely soaked and the room was generally a disaster. Michele was on the futon. I stirred her to ask what the hell happened. She told me we came upstairs, and I took a digger face first into my bookshelf (see attached photo).
I was then informed that things were going according to her plans until I told her to dismount, and preceded to unload what she described as "three gallons of piss" all over myself and the bed, intermittently referring to my penis as Old Faithful and humming God Bless America. Spoiler Alert - Our relationship didn't last much longer after that.