If I’m not mistaken, I have previously made a few (20 or 30) passing references to my bad luck with women. But until now, I haven’t really gone into detail on any of it. And I think it’s time for that to change. What better way to start it off than with a ridiculous first date story?
Now, before I get into the bulk of it, I need to give you a bit of back-story. I met this girl through a co-worker at a birthday party. I’m not quite sure what sealed the deal for me, whether it was my off-key singing, my rhythmless dance moves or my awkward conversation, but by the end of the night I had her phone number. The next day, after I overcame the initial shock of this actually happening, I texted her (and she surprisingly responded). We talked for a few days and she agreed to a date. If you’re still with me at this point, I assume that you are as surprised by this chain of events as I was.
I spent tens of minutes poring over every single detail before the date actually happened (I’m a guy, it doesn’t take me very long). I made sure my hair looked nice, my clothes matched and my breath didn’t stink. I picked her up in my extremely impressive Chevy Cavalier (a vehicle that obviously says “I save money on gas so I can buy you nice things”). I did the gentlemanly thing and opened her door for her, walked around to my side, got in and started the car. This was my first indication that something might be wrong: my car struggled to start. In the 9 years of having the car, I’d never really had any trouble with it, and it still started on the first try, so I figured I’d just get it looked at later.
I drove to the restaurant, parallel parked (terribly) and we sat down for a nice dinner. Dinner itself went well (I think). To most outsiders, I would have seemed like a guy that doesn’t regularly put his foot in his mouth during normal conversation. Unfortunately, after our food was done, the waitress apparently forget that we were supposed to pay and the two of us sat there an extra 30 minutes desperately trying to flag down a waitress while making obligatory jokes about how the meal must be free. Eventually, the meal was paid for and we went back to my car.
This is where the night comes to a screeching halt. As I turned the key in the ignition, my heart sank. My car refused to turn over. Naturally, I made the obvious joke and exclaimed, “I swear this has never happened before,” before (suavely) following it up with “I heard a lot of guys have performance issues…” I stared meekly under the hood and then made two phone calls. First to a friend to come pick us up, and second to a tow company to take my car to a shop. Then, because we were right outside a bar, we went inside for a few drinks while we waited.
My friend arrived far more quickly than the tow truck. Thankfully, he had no idea what was wrong with the car either, so I didn’t look like a total doofus. He then joined us at the bar for what was the absolute definition of a third wheel situation. Now, I have to give him credit for sitting off to the side and letting my date and I talk on our own. But it also ended up feeling like a parent-chaperoned date, where you dad tries to make himself scarce by sitting 2 tables away from you. It got even weirder after the tow truck came. Since my friend was driving us home, my date sat in the backseat. And since I didn’t know what else to do, I sat in the backseat with her. I never went on any dates before I was able to drive, but I am now abundantly aware of how awkward they would have been to have a chaperone. We alternated between hushed conversations in the backseat and trying to include my friend in the front seat. And by the time we dropped her off, I wasn’t sure if I wanted to lock myself in my room and listen to angsty music or for my friend to pat me on the should and say “I’m proud of you, sport “(is that how middle school dates ended?).