Since I have a crazy and fluid job, which is difficult for many people to understand, and a bank account that is in desperate need of a Government bailout, (if anyone has Ben Bernanke’s direct line please email it to me) one would rightly assume that the chances of me going out on a date with an attractive, successful lawyer were slim; however, I proved all the skeptics and naysayers wrong when I recently went out on a first date with such a woman.

We texted during the day and ended up choosing an Urban BBQ restaurant for dinner that was near her apartment in River North, which is a very trendy area just north of the Loop. I left work around 7:15pm and picked her up promptly at 7:45 so we could make our 8:00pm reservation. The restaurant was just under a mile from her apartment so I quickly navigated through the city before beginning the (often times) laborious task of searching for a parking spot. Since the weather was cold and rainy I was praying we would get lucky and find a spot within a block or two of the restaurant, and after driving around for just a few minutes we fortunately did.

Now, for those of you who are unfamiliar with how parking throughout most areas of Chicago works I will explain our system so that we are all on the same page. Essentially, a few years ago, the city privatized all street parking, and the company who bought the right to charge for parking tore down all the old-fashioned parking meters and replaced them with pay-boxes. Tall signs with green writing and arrows indicate where pay-box parking is allowed, and if you find a spot within one of those designated areas all you have to do is simply find the closest box to where you parked and, using coins or a credit card, purchase up to two hours worth of parking time.

After parking in a coveted pay-box spot that we had found about two blocks from the restaurant I bought my ticket and placed it on the curbside area of my car’s dashboard. With that exercise completed, we briskly walked through the elements to the restaurant and had a lovely dinner. The food was excellent, the conversation was interesting and she seemed to be having a very nice time. Even though throughout much of the dinner I felt slightly uncomfortable since she was obviously an independent, successful women and I’m, well, me – a financially limited, work obsessed– albeit dashingly handsome–College Basketball Coach, I tried to remain confident and be myself.

Anyway, so we have a nice time at dinner, and after taking care of the check we leave the restaurant and head back to my car so I can drive her home. During the short walk I debated in my head how I wanted to play things, and tried to figure out what was my best course of action in asking for a second date. Yet, I was abruptly forced out of my daydream and back into reality when we turned a corner and, wouldn’t you know it, my car wasn’t there. In a moment straight out of the classic stoner comedy, “Dude Where’s My Car?” she literally turned to me and asked, “Matt where’s your car?”

For whatever reason the first thought that came to mind was that we had parked further down the block, but it didn’t take much of a “Spidey Sense” to realize that we were standing in the spot where my car should have been. The next thought that jumped into my head was that my car had been stolen but the fact that I own a 2004 Mitsubishi Lancer with two missing hubcaps and several cosmetic scrapes on the sides was probably a pretty good indicator that it hadn’t been jacked. Furthermore, while I was contemplating what type of individual would be desperate enough to steal my car, my date noticed a sign at the end of the block, which we had missed when we originally parked, indicating that while I was in a valid pay-box spot, and was not over the time that I had paid for, I was unfortunately in a spot that was designated for taxi cab parking only between the hours of 5pm and 2am.


As it sunk in that my car had been towed, while on a first date, no less, I remained remarkably composed and calmly pulled out my phone in order to find where I could retrieve my displaced automobile. Even though she felt terrible, and was very sweet and understanding about the whole ordeal, I figured the best thing to do was put her in a cab home, bail out my jailed car and try to forget about how, at the last second, I embarrassingly blew my chance with a successful, attractive lawyer.