Welcome to Great Moments in Drunken Hookup Failure, where we showcase four heartwarming true stories of drunken love gone horribly awry. Off we go.
My friend asks me if I want to take in a night-game at Wrigley, so oblige him, being that it is late in the season, the Cubs are out of the pennant race, and the tickets are free season tickets belonging to his company. It is a slow game and a rather crisp night out so we decide to head to a bar nearby about the bottom of the 8th. Fueled by cheap, shitty and multiple stadium beers, I decide to text a dude I had met out at a bar a few nights earlier. He relays to me that he is still at work near the stadium and will meet me within the hour. My pseudo date/hookup arrives looking as hot as I recalled, yet wearing a Cubs tee with marijuana leaves on it. Obviously, this seems off since he just came from work. We start making small talk and my friend, being a dick, asks my dude where he got his shirt. "Oh," he says, "I made it. My friends and I hawk tee shirts outside of Wrigley on game days." Awesome. Just awesome. He's a loser.
But it gets better. Since I am pretty impaired and trying very, very hard to look past his present career path (he later tells me he actually has a college degree from my Alma Mater, and is having a hell of time landing a job in the city given the state of the economy), so I decide to throw this dude a bone. He seems to be a victim of the times—and smoking hot. We imbibe some more drinks, then my friend gives me that knowing, disappointed look (don't do it!) and hails a cab home, reminding me to be careful. Whatever. I continue to drink heavily and learn more about my new prospective boy. It turns out he has an engineering degree (yay!), lives at home with his parents (boo!) and seems like someone I could actually see myself dating—after he ditches the tee shirt business, of course. There is potential there.
We finally make plans to share a nightcap at my apartment. Once we get home, the heavy petting begins, clothes come off and the drunken hookup proceeds. I am not making good decisions at this point, but decide I should probably fuck this guy. I stumble off to the bathroom to retrieve a condom (boy is of impressive size and build) and leave my boy alone, only to re-enter my room moments later to find my boy smoking a huge bowl! If the shirt fits...you know? He asks if this is okay and I allow it. Again, whatever. Well, he ends up packing and smoking 2 bowls while I wait naked with a prophylactic in hand. I am starting to lose interest in sexy time with him.
And then—this is where it gets good—Stoney Mc Stonerson actually lights my pillow on fire. The dude was so fucking high he somehow managed to catch my goddamn bed on fire (seriously, how can you smoke that much weed, but use matches instead of a lighter)! I panic, he grabs his shirt and beats my bed/pillow until the fire goes out. I ask him to leave immediately—in his now hole-ridden, burned out Cubs marijuana shirt. What the fuck? I believe this was a cockblocking by the recession, weed, fire and the Cubs—yes, I am blaming the Cubs on this one too because they didn't make the post-season.
He earned that cockblock, that's for certain.
It was the summer before my senior year of college. A couple of my friends from high school were having a joint 21st birthday party. One of the girls was loaded and her parents rented out a room at the local country club. It was essentially "My Super Sweet 21st", everyone is dressed up and ready to get weird. She went to a different college, and naturally some of her college friends made the trip. I made it known to my buddies that I'm going in after her friend from college, let's call her Julie. I "buy" (open bar) Julie a couple drinks and she's seemingly receptive, awesome.
The birthday girls' parents have agreed to throw an after party at their nearby mansion. They even had car service for 40-50 drunk college kids, pretty awesome people in retrospect. There are literally 20 bedrooms in this place, so I find one to stake claim for Julie and I, leave my coat and possessions and go find the party. Julie has made her way out to the back porch where there is a hot tub built into the deck (remember, built INTO the deck...). She asks "you want to get in?", as she's stripping down to her underwear. I'm down to my boxers in 3 seconds and we're in the hot tub. Heavy petting, make out, and her top coming off ensue... A group of our friends decide to come out on the porch and join us...uninvited.
So Julie is sitting on my lap, topless while 6 or 7 other kids (including the topless birthday girl) join us in the tub. There are roughly 400 too many pounds in the hot tub, and a significant amount of water is displaced. An hour or so passes and it's just Julie and I again. She's eager to do the deed right there, but I suggest we go back to the room I had previously acquired. She agrees, so we gather our possessions. My pants, shirt, socks, and shoes were conveniently placed right outside the hot tub...they were soaked from the overflow, success.
By this time it's 4am and everyone else is passed out. I run inside to try and find some towels, but to no avail. I come back outside and she's on the phone (pretty sure with her boyfriend), and she says she'll be inside in a minute. I decide to sit by the door so I don't miss my opportunity...plus she doesn't know where our room is. 10 minutes pass, and sitting has turned into laying down passed out in my wet underwear. For god knows what reason, she wakes me up when she comes inside. We make our way to the room, locked, no answer.
She suggests we go into the movie theater (yeah, in the house), and grab a recliner. We stumble into the room where 15 other people are sleeping and find a recliner. On the way in I tip over a 20 lb floor speaker onto a group sleeping on the floor, effectively waking everyone up. Once we find the recliner, we're greeted by the birthday girl getting it on in the chair directly next to us. Julie was not down for the orgy, so we passed out. The next morning I wake up in my damp boxers to everyone asking "who broke the floor speaker?"
Were the rest of you let down that the deck didn't collapse and injure 37 people? Because I kinda was.
The summer before my Senior year of undergrad I did a month long study abroad in Costa Rica. My group would take an excursion out of San Jose every weekend so we could get out of the city and see the country. My last weekend there we traveled to Puerto Viejo; a dirty little surfing town on the Caribbean coast. The weekend started off normal enough; smoking schwag weed bought from sketchy locals and getting shit faced on cheap Imperial all night. After a few hours of pre-gaming, we decided to make our way to one of the clubs on the beach.
The club seemed decent enough; with a huge beach party and reggaeton blasting throughout the place. I was losing my buzz so I made my way across the dance floor to get to the bar. All of the sudden, I felt a hand on my ass and someone spun me around. In front of me were a cute Asian (...Emily? I think) and her friend smiling at me. They both started grinding and dry humping me on the dance floor. I instantly forgot about getting more beers and joined in on the dance party. Emily's friend eventually left us to meet other friends on the beach. We started a heavy makeout and heavy petting session on the dance floor.
With a 12 pack of liquid courage in me, I felt that I could make this go further if I got her away from the dance floor. I eventually talked her into leaving the club and heading about 50 yards down to the beach. We sat down on a fallen palm tree and got back to business. Her hand slowly making its way up my shorts, I figured I was about to get blown on the beach. All of the sudden, I felt something hard in my back and a thick Hispanic accent in my ear; "Give me all of your fucking money or my friends and I will kick your ass". I turned my head and saw a local with a gun in my back and 10 of his friends 10-15 feet behind him. I cleared out my pockets and she cleared out her purse, it was probably only $20 combined from both of us
She was shaken from the incident, but me being drunken asshole figured I could turn this emotional vulnerability into another hookup. We got a ride back to her resort from a couple of sketchy dudes who were trying to hook up with her friends. I tried to start up our hookup again, but she was starting to sober up and repeatedly denied me. We took down a few more beers and I passed out on her hotel room floor. The next morning, I ended up walking four miles back to my resort and getting berated by our trip director for disappearing the night before.
My freshmen year at a mid-size college outside of Philadelphia I decided that a keg race would be a great start to the beginning of a Friday night. I'm 5'11, 160 pounds, not the strongest body frame for a heavy drinker. Seeing as that was our pregame we decided to go out to a party. I was understandably pretty drunk at this point and a friend of mine introduced me to a girl, we'll call her Jess, from his high school (mainly because he didn't want to deal with her so he pawned her off on me.) Seeing how I had the perfect combination of natty light and parliaments going through my system I must have said something smooth because after 15 minutes of talking to this girl we were making out and she asked me to go back to my dorm. I somehow managed to navigate my way through the basement and up the stairs with this girl and just as we were about the exit the door a friend of hers asks Jess where she is going. Jess responds with an answer that immediately sobered me up. In front of about 30 people Jess replies, "I'm going to fuck this freshmen." That comment was met with a mixed reaction from the crowd but whatever I just found out I was getting laid and was pretty excited. Getting laid was a relatively new experience for me so I jumped at any chance I could get.
Now I need to set the scene at my dorm. I lived on the second floor, directly above the spot where all the smokers stood while they smoked. Everyone at this college fucking smoked especially on Friday night. It was an unusually warm spring night so my windows were wide open. So we shut the door to my room and immediately start going at it. What I didn't know and would soon find out is that this girl had a reputation as being extremely loud. I'm talking freight train loud. Me being drunk as shit and horny I think nothing of it except that for all my inexperience I must be pretty good at this but there were definitely a few times where her loudness was way over the top.
So after a while of nonstop fucking in every way my mind can think of with this girl screaming the whole time I hear a knock at my door followed by the phrase campus security. Now this is something that me and a friend of mine Steve (the same kid who set me up with this girl) who lived down the hall used to do. He got a lot more pussy then I did so it was usually me knocking on his door fucking with him. So I reply, "fuck off Steve", which is then followed by "we don't know who Steve is, but you should really open the door or else we will. So I say "fuck you Steve, there is no way you are getting in here." That's when I hear the sound I will never forget, the sound of the key going into the lock and the door kicking open.
I look at the door and I see three campus cops, two of which were laughing so hard they couldn't enter the room. Behind the cops is no lie about 50 students in my door frame with the smaller ones in the front with the taller ones behind them so that everyone could see. I think they choreographed it. The cop who manages to keep it together looks at me in complete disbelief and says, "do you have any idea how many people are outside your room right now, seriously look out the window."
Well all I have on at this point is a condom and a sock and I'm trying to throw my blanket over the girl so that no one can see how ugly she is. I stand up and open the curtains and no lie there is about 250 students outside who see my face through the window and they just go crazy. I look over at the cop and say something like "well what now" and the cop just goes "Jesus fucking Christ kid, will you put some pants on." So I try to get some sweat pants on but I'm drunk and nervous and in the process end up falling over a coffee table. It was pretty obvious that there was some underage drinking going on.
The cop shuts the door with me lying naked on the floor and explains to me how because of all the people outside he can't take me out and that really he just wanted to make sure nothing too wild was going on in the room and that everyone was ok . He cites me for a noise violation and tells me to finish up and go to bed. I can't finish so I wake up alone the next morning with a note from the girl who says she's sorry and how embarrassed she is and a noise violation. Any time you get cited at this school you have to write a 2-page paper explaining what you did and how you can prevent it from happening again. Fast forward a week later with no contact with this girl. I come back to my dorm room after class and I find a two page paper typed up tacked to my cork board with a note explaining how it wasn't fair that I take the heat for something we both did. Pretty cool move on her part but still to this day we have never spoken to each other since.