I had about nine months at home in Florida post-college before moving to New York, and it wasn't until the last few weeks that I had my first and only date while living there. Granted, a big piece of this was because I was sick for those first six months, but it also had a little something to do with the dating pool at the time and my utter lack of social life. However, as I was getting my hair freshened up in advance of the big move, a guy came into the salon for a trim. He was about my age, quite engaging, and vaguely familiar - it turned out we went to high school together, although we didn't really cross-paths. As I sat there chatting with J., I realized that this was the most interaction I had had with the opposite sex in, well, nine months; so before I knew it I agreed to go out with him that night. Problem was, I had also agreed to meet up with an old high school friend that night. Rather than cancel either plan, I figured why not do a complete throwback to high school and make it an awkward group date...little did I know just how awkward this would get.
I met up with my friend first, I am still unsure how I talked her into going along with this plan, but bless her soul because she was game. We got ready and then headed over J.'s house. Upon walking in, the first thing I noticed were the Playboys artfully arranged on the coffee table as reading material for guests. Nothing says classy and mature like adult magazines fanned out in the middle of the living room. He gave us a tour, which included his handgun collection, rifles, and samurai swords. We didn't stick around his place for too long, instead we headed off to dinner.
A Friday night date called for margaritas and dinner at Applebee's. Since we were drinking, we didn't want to go to far from there, so we headed down the street to Club 41 - one of the diviest bar in town. Shockingly, it was my first time there...we walked in and were met by a layer of smoke. It was still pretty early when we arrived, so we were able to play a couple games of pool and have a few drinks. As it got to be later, we started to see a shift in the crowd. I decided it was time for us to go somewhere where we stood out a bit less, when I turned around and saw the largest woman I had ever seen walk in in the smallest gold lame top I had ever seen. I couldn't take my eyes off of her, as she shoved her way towards the bar, pulling along a behemoth of a man clad from head to toe in leather, once there she spat on the ground and ordered two shots of Jim Beam for her and Tiny. It was definitely time to head across the street to the new bar that had opened up a couple months prior.
Shockingly smoke free, it was nice to look around and recognize at least half the crowd, not as nice was seeing my parents. Apparently they had been inspired by my date night and had decided to have their own and we had just stumbled into the middle of it. I should take a moment here to mention that somehow in the course of the first half of our awkward group date, J. had taken a shining to me. I not so much to him, but I was enjoying being out so I wasn't willing to cut the date short. Instead I mentioned my impending move to J., hoping that would cool his jets...he did not see it as a deterrent to our budding relationship. And thus, given the chance to meet my parents, instead of finding it awkward and suggesting to get a seat elsewhere, he asked if we could join them. My friend, who was quite fond of my parents, was happy to have other people to talk to and readily agreed. So our group date expanded to include my parents.
I'd like to say that at this point I decided to call a spade a spade and end the date, but I didn't, so I will take a moment to once again stress that this was my first night out in nine months. And so we joined my parents table, I went and ordered drinks while J. laid out his plans to come visit me once I was up in NYC to my parents. When I returned to the table my parents were both horrified and totally entertained by my situation and quickly offered to play darts with us. The conversation continued to circle around my future with J., no matter how I tried and steer it away, and my parents - completely enjoying themselves and my discomfort - egged the conversation on and then escaped to chat with other people they knew at the bar. My friend abandoned me to catch-up with some friends - so I was stuck at the back of the bar trying to talk him out of buying tickets that night and instead waiting for me to get settled before he planed his grand visit. By the grace of all that is holy the bartender finally did last call, and I could sense my escape, I saw my parents dart out the door with a snicker and a wave, and I was prepared to call it a night. Only J. and my friend decided we needed to close it out in true hometown style and the next thing I knew we were at Perkins.
I wish I could say that we grabbed some fries and sodas and the night finally ended. However, we ran into a couple people from school who my friend knew - they happened to be big shots from back in the day and my friend had had a crush on one in school. Problem was, it turns out that J.'s ego was a bit sensitive and he didn't like being upstaged by three dudes, who were now getting all the attention. We were all joking around and J. started getting quietly belligerent and the next thing I knew a chair was getting knocked over and there was talk of taking it out into the parking lot. I'd like to remind you once again that - We. Were. In. A. Perkins. So yeah, at this moment, I had had enough and so had my friend. We excused ourselves under the guise of using the restroom and covertly paid our bill and escaped to the parking lot. Once I made it out I realized that J. had left his car somewhere along the way - and in a time before Uber and living in a small town, this meant he really had no way home. Not able to be a complete jerk, I instead had to go back in and admit to the 3am Perkins crowd that the most embarrassing person in there was with me. Talk about a hometown humiliation. I extracted him, drove him home, and finally crashed.
The next afternoon I awoke to 12 texts from J. asking me out again and then annoyed that I didn't immediately reply. I tried to let him down easy, but eventually had to be blunt, and finally I had to figure out how to block a number. When I stumbled into the living room I discovered my parents waiting for me with coffee, Tylenol, and Cheshire cat grins waiting to roast me - because when your first date with someone ends up being a double date with your parents that ends with an almost fight in a Perkins parking lot...what more can you expect the next morning?
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