On Dating: A Journey from Mom Jeans to Marriage

In the film When Harry Met Sally there’s a scene where Carrie Fischer and Bruno Kirby (Jess in the movie) talk about how glad they are they found each other. The two thirty-somethings entered into a nice, comfortable relationship, thanks to Harry and Sally.

Marie and Jess were happy to not “be out there” anymore trying to date randos. That’s how they should’ve felt. Dating can be brutal.

In middle school, I launched my unprolific dating career. This is what it looked like: I sat next to this girl, April, at lunch and we rubbed legs — which to me was a monstrous, life defining deal at the time.

Seventh grade was great. I had a wonderful teacher, a portable CD player with ESP, a Milwaukee Bucks Starter jacket (classic, but not as classic as a Hornets Starter jacket), spent most of my time with my best friend, Bernard, and I played sports. But the delicate leg rubbing at lunch, in class and on the bleachers in the gym during basketball games was the pinnacle of my life up to that point—easily the most exhilarating thing I’d done. I shouldn’t remember it as well as I do. But I do.

She wore corduroy, I wore my mom’s jeans.

That’s a true thing you just read. I wore my mom’s Eddie Bauer pants for a few months in grade school. I remember liking them, but I also remember being made fun of slightly because they were really saggy in my rump region—because they were mom jeans. But I wore them with a No Fear t-shirt so whatever.