Welcome to Great Moments in Drunken Hookup Failure, where we showcase three heartwarming true stories of drunken love gone horribly awry. Off we go.
My buddy is a trust fund asshole who got to spend a year touring the world right after college. I went straight into grad school while working full time but managed to find a two week window in which I could fly out and briefly join him on his journey. After some deliberation we settled on Southeast Asia because it was cheap and we heard it gets really wild.
I met him in Bangkok where we made the rounds at the ping pong shows and did our best not to get accosted by Ladyboys, before heading to Bali for a few days. Our first night in Bali we met a tiny Indonesian man called Jeffrey. He didn't know much English but was VERY excited to talk to us when he found out we were Americans. The conversation was pretty one sided, he mostly quoted American pop culture stereotypes like some kind of low-rent Indonesian version of Bill Simmons. He said things like, "What's up maaaann?" in a surfer voice, or "Los Angeles! New York!" After a few minutes of this we parted ways but he soon found us inside a bar. Despite the language barrier and slight annoyance he was a somewhat entertaining novelty so we decided to buy him a drink. This proved to be a fatal decision.
Anytime we were able to strike up a conversation with a group of Australian girls or European backpackers Jeffrey made sure to step in and drunkenly insert "popular" American commentary.
Me: So where are you all headed next?
Backpacker: We'll be here until Thursday and then we...
Jeffrey: EMINEMMMM! 50 CENTTT!
Backpacker: So is this guy with you or...
Finally around 3 A.M. we met some Scottish girls that didn't seem too bothered by our new and now very intoxicated friend. I hit it off with one girl named Haddie. Within 20 minutes we were making out on the dance floor. When she invited us back to the house they were staying at I was pretty excited. However there was only one condition...no Jeffrey. No problem, right?
We walk outside and tell Jeffrey we're headed home and it was great meeting him, we now consider him a true friend, etc. etc. To which he responds, "I go with you." We tell him this isn't possible but maybe we'll see him later in the week. Thinking we've shaken him my buddy and the Scottish girls get into a cab. And wouldn't you know it, right as the cab takes off Jeffrey hops in.
We plead with Jeffrey to get out but also can't stop laughing at the ridiculousness of the situation. There was one person who wasn't laughing though...the girl whose family owned the house. When the cab pulled up she got her Mom who came out and yelled for, "The two American Boys and that dirty Indonesian to get the FUCK off her property."
Haddie gave me a hug and kiss goodbye, made a frowny face and said, "I'm sorry."
I turned to Jeffrey and said, "God damnit Jeffrey..." to which he replied, "What's up maaaannnn?" and laughed hysterically. The amount of joy that permeated through his cackling laughter was rivaled only by my hatred of him in that moment. I never saw Jeffrey or Haddie again.
My sophomore year of college my fraternity did our semester formal in Vegas. Pretty standard protocol as Vegas was not that far of a drive from where I went to school. I'd been kind of hooking up with this girl Megan for a couple months prior to formal, but we hadn't had sex yet. After she agreed to go to formal with me, I figured two nights together in Vegas, it was definitely going down.
The first night in Vegas came around and everyone in my frat and their dates were out and about on the strip, having dinner, drinking, gambling, etc. One of my wealthier friends had just turned 21 and to celebrate his parents reserved him a suite at the Bellagio for the weekend (the rest of the house was staying at Caesar's...I digress). My date and I, not being 21 yet and therefore unable to check out any of the clubs, decided to go over to my friends suite at the Bellagio where he was having a party. After getting thoroughly drunk/flirting/making out at the party, we decide to go back to our room at Caesar's and continue the festivities. I tell my friend that I'm sharing the hotel room with not to come back for a couple hours and think all is well. Once we're back in the room at Caesar's we start getting busy, clothes quickly come off, and I'm well on my way to pound town when I hear the door to the hotel room open. Thinking it's just my friend drunkenly coming back I tell him to fuck off when not one, not two, not three, but FOUR large (like, really huge) Mexican men walk into my hotel room.
Turns out Caesar's Palace double booked the room we were in and four guys also ended up with keys to my room. So my date is screaming/crying trying to cover herself up while I'm arguing the ownership of the room with these four guys still fully nude. Anyway, after calling down to the front desk (from the bathroom because for some reason these four guys still refused to leave the fucking room) they say I need to come down and sort the issue out in person, no way to do it over the phone. Megan has covered herself up with a towel at this point and I in my drunken stupidity try to reignite the evening in the bathroom while the four guys are still standing in the room, but she's having none of it. Ultimately, we ended up getting a $100 bar credit (which is fucking laughable in retrospect) at all Caesar's bars for our "inconvenience" and we both blacked out the next night and were too drunk for any sort of sexy time to occur. I never did end up getting to seal the deal with her. Moral of the story: dead bolt your hotel room kids. Oh and fuck Caesar's Palace.
I was headed to a good friend of mine's birthday party at a trendy downtown apartment with a couple of buddies. We were dressed to the nines, ready for a big night on the town. We arrived at the apartment, met all of her friends and started pouring booze. One of her friends, a tall, gorgeous redhead started talking to me behind the bar for a few minutes and we hit it off. After several drinks, we headed to a bar a couple of blocks away. There was a lounge singer, cheap drinks and ashtrays on the bar.
Each of my friends was paired off with a girl by closing time and they all piled into cabs. My redheaded companion and myself decided we wanted to keep the party going, so we headed to an afterhours spot in a shady part of town. We entered the bar, which was about half full and headed to a booth near the back. We started making out and engaged in some heavy petting. A bouncer got wise to our sexual activity and asked us to leave. No cabs were to be found outside of the bar as it was nearing sunrise (this girl was a champ). After walking for a few blocks, we found a cab and headed back to her place as daylight grew.
What she had failed to tell me is that she still lived with her parents in a very nice neighborhood. We arrived at her place and she told me to be quiet as possible. We headed to the family's carriage house behind the massive mansion. She led me upstairs to the guest bedroom above a spare garage. With the sun peeking through the curtains, she tore her clothes off, revealing an incredible body. We tore into each other like a couple of drunken beasts and started doing the deed. I was laying down on the bed as she pulled my trousers down and started doing wonderful things with her mouth. I kicked off my shoes and they loudly hit the floor.
What we hadn't realized is that her father was below, doing some early morning maintenance on his '67 Mustang and heard the loud clack of my shoes hitting the floor. We heard someone open the doors downstairs and come up the stairs. I was paralyzed with fear and she had stopped performing on me. I looked up and saw dear old dad standing in the doorway, glaring at me. Calmly, he picked up my shoes and pants and simply said, "get out."
I collected myself and headed outside. My phone had died and I was miles from my apartment. Drenched in shame in the early stages of an awful hangover, I had to ask her dad to use his phone to call a cab while he glared at me the entire time, silently sipping on his coffee. A $30 cab fare later, I crashed into my bed.
Later that evening, she called me and apologized. A week later we went on a date and decided to leave it there. Still haven't hooked up with a redhead.