#MyWorstDate started with shots of tequila, a stranger in a bar, and a mysterious fluffy cat (as many do)... but ended in a way I never saw coming.
When I was 23, I lived with 2 roommates in a shitty apartment in downtown Chicago. Even though I was broke, I hit the early 20s jackpot because the guy I lived with worked at a famous club that hosted amazing DJs, and he would put my other roommate, Jen, and I on the VIP list every weekend. I was commuting 4 hours a day, and Jen was still in school part-time while working full time, so by Friday we were always ready to blow off steam.
One particular weekend, Jen came home especially annoyed with her job, complaining about the boss she couldn't stand, and I had just finished a long work week, so we decided to make it a good night. We started at our usual spot, and after a few hours of dancing and tequila shots, Jen decided she was exhausted and it was time head home. I hung around for a bit longer, and then decided to meet up with an old college friend who was at a low key bar nearby.
By the time I got there, I was feeling fine as wine, and started chatting with a cute 30-something guy while waiting for drinks at the bar.
"Do you wanna smoke some hash?" he asked me, when I leaned over him to grab my drink.
"I would," I nodded, "but it's freezing outside."
He glanced around the bar, and grabbed my hand. I teetered on my heels behind him until we got to an isolated spot in the far back corner. We were in a cove behind the pool table, barely visible to the rest of the bar, and he pulled out the hash for us to smoke. After a few puffs I was feeling delightful, and continued to dance and flirt with him until finally last call came.
"Want to have a nightcap at my place," Hash Guy asked, "I am just around the corner."
"Give me just a sec, let me say goodbye to my friends."
I paused a moment to assess the situation. He seemed harmless enough, plus, my college buddy knew him from some softball league he was on. I figured that was good enough, so I said bye to my friends and we left.
Hash Guy was cute—he was average height with glasses and a thick head of curly black hair—but I could tell he wasn't great at talking to women. Despite his awkwardness, he was clever, and super nerdy, and we laughed as we walked back to his place a few blocks away. The freezing Chicago air was like a slap in the face, and by the time we got to his building I had pretty much sobered up.
When we got to his apartment, he kicked off his shoes outside his front door, and I attempted to follow suit. I was wearing knee-high heeled boots, which aren't the easiest things to get on and off gracefully, so I struggled with them for a few minutes while he went into his apartment. By the time I made it in, he had the lights off, a Glade air freshener candle lit, and was fiddling with the stereo. I leaned on the arm of the couch, but nearly fell off when I heard the song he was playing.
"Let's get it onnnn... Let'ssss get it on." Marvin Gaye filled the small apartment and I had to surpress a laugh. What. The. Hell.
"A little Marvin?" he said, winking at me. He did an awkward body roll/shoulder dance, and I cringe smiled back.
"Get comfortable, I'll grab some wine," he said, over the music—which was playing way too loudly for any kind of romance vibe he was trying to create.
I sat on his tan plaid couch, and a few seconds later a GIANT white fluffy cat came walking out of the open door to his bedroom. The cat had a pink studded collar on, and when it brushed against my leg I thought maybe I was hallucinating. It seemed like such an odd thing for a single guy with a sparse apartment to have this cat that looked like it should be named Princess and carried on a satin pillow.
Hash Guy came out of the kitchen with some wine, and I asked him about the cat, thinking maybe he was cat sitting.
"No, she's mine," he said, scooting closer to me, "isn't she so cute?"
I ignored the question and took a big gulp of wine. After making out for a while on the couch we went into his bedroom. He grabbed a t-shirt for me to put on, then went into the bathroom. When he came back out, he was wearing a flannel pajama set with reindeer and snowmen on them. At first I thought he was being funny so I laughed, but he just climbed on the bed and stared at me,
"What's so funny, sexy?"
Oh God. Any tiny shred of attraction I had left slowly drained away.
At this point, I knew it would be a one night stand, but I figured I would go through with it for the story alone... my roommates and I spent many a Sunday morning sharing tales of the weekend, and this one kept getting funnier.
We eventually hooked up and he asked me to stay, so I rolled over and waited until I thought he was in a deep sleep. I wanted to try to sneak out, he was a nice guy, but just not for me and I wanted to avoid any awkwardness, so I tiptoed as quietly as I could back out to his hallway. I grabbed my boots, knowing there was no way I was gonna be able to put those suckers back on without a crowbar and a team of 10, and made my way to his elevator.
He lived in a loft building that had one of those old-timey elevators with doors that open from the top and the side, and a long metal bar that keeps them shut. It seemed so cool on the way IN 3 hours earlier, but now, for the life of me, I could not figure out how the hell to open the doors to the elevator. I had locked the handle to his apartment door when I left, trying not to be a complete asshole, so I knew I was in a real pickle.
I was stuck at 5am, wearing my party girl dress, braless, holding my boots in my hand, stuck in trendy loft purgatory—unable to get back into the apartment or into the elevator. I poked around trying to find a staircase, but the only door I could find was locked.
Heaving a giant sigh, and with my head already starting to throb, I went back to Hash Guy's door and pounded as loud as I could. I leaned my ear against the door...nothing. Pounded harder. And again. And again. After several minutes, FINALLY, I heard footsteps coming to the door. I told him I had to be at work in a few hours (little white lie) and didn't want to wake him, and would he be so kind as to open up his elevator for me. He nodded groggily and put his finger up, then disappeared into his apartment for a second. When he came back he handed me something,
"Here's my card, you should give me a call tonight."
I nodded back vaguely, shoving it in my pocket. We had the awkward goodbye I was hoping to avoid, and I gave a small wave as the elevator shut. I stumbled barefoot out into the freezing morning, and flagged down a cab. When I arrived back at my own apartment it was 6am, and I was exhausted and bleary-eyed, still carrying my boots with half my bra spilling out of my purse. My roommates were sound asleep, so I took a fridge magnet and stuck Hash Guy's business card on the fridge, grabbed a glass of water, and fell into bed, excited to tell them the story when I woke up.
That afternoon, after I finally got some sleep, I wandered out into the kitchen where both roommates were sitting at the table nursing coffee and hangovers.
"Oh hey Sleeping Beauty, what time did you get in?" Greg asked me, "I got in at 5 and you still weren't here."
"Yeah," Jen chimed in, "someone partied last night. Um, and please explain why my annoying boss' business card is on our fridge?"