1994 was the summer that I finished university, baseball went on strike, I moved in with one of my sisters, and I tried to figure out my life.
For a year, I lived with my sister in her apartment, Cambridge Towers, on the corner of Cambridge and Taylor. I was there to help her fill some of the void left by her ex-husband. Unsure of myself and my place in the world, I tried my best to cover the empty spaces of someone else’s broken heart. I slept on the couch, listening to trains whistle through the night.

I was—and in many ways still am—quiet, shy, well-mannered. I was also mostly unsure of a world I didn’t understand and often felt ill at ease engaging within it. But I had a few close friends after university, and they helped me navigate life.

We had a night out planned: pool in a downtown pool room. Not seedy, but upscale. It was on the third or fourth floor of a well-kept building. I no longer remember the name of establishment, but it was perfect for us post-university types.

I was excited to get out of the apartment and spend time with my friends. I missed the consistency of seeing them every day on campus. Not one for going out very often, I spent a long time figuring out what to wear. My best idea was navy Docker pants, a paisley-patterned shirt that, because I was rail-thin and quite short, neither fit me well nor looked particularly good on me, and a pair of black knock-off Oxford loafers with tassels. I thought the tassels made the shoes and hoped the shoes would make the man.

So, I was dressed as well as I could, but I was filled with nervous energy. There were five of us: myself, my best friend Mike who I would live with the next spring in Osborne Village after I moved on from my sister’s place, G and M – who had just gotten married earlier that summer, and L. We had all met and become friends at university, and I liked L.

She was fun, a bit quirky, but also gentle and kind. We bonded over Hitchcock movies (I called her up at midnight once to let her know that The Birds had just started on one of the tv channels) and Breakfast at Tiffany’s—the film and, a year later, Deep Blue Something’s song of the same name.

We had agreed to meet at the building at 8 p.m. I was the first to arrive, followed shortly by G and M. Ten or fifteen minutes passed, and then L arrived. Finally, Mike pulled up a few minutes before 8:30.

We went upstairs to the pool room and grabbed drinks, a rack of balls, and a table near the back corner. When I say “drinks” I mean I drank overpriced Cokes all night long—I wasn’t drinking alcohol back then. I mention this now to make it clear: I was completely sober throughout the evening.

We quickly got into playing pool. In the first game, I believe the guys played by sinking numbers (1–5, 6–10, 11–15) instead of solids and stripes, while M and L chatted, catching up after a few months apart. After that, we kept mixing and matching players and teams.

At some point in the evening, I had a long shot to make. I was leaning on the table in such a way that my right foot was off the ground. As I took the shot, I felt my shoe first come off my heel, and then—in cinematic fashion—it slid completely off my foot.

I remember all of this so clearly: the back corner table, with walls on two sides affecting our play; the feel of the table as I lay across it; the shoe falling neatly off my foot; the laughter at how badly I missed the shot, along with some chuckles about my shoe.

And yet—how is it that I recall so little after that?

Was I distracted by hanging out and chatting with L? Of course. Did I play the rest of the night with only one shoe? I must have, I suppose. How come no one else noticed or commented? I have no idea. Did we look for the shoe at the end of the night? Did I simply not notice? Not care?

I told this story to my son recently. He said, “I can understand losing a scarf or a mitt—maybe even a jacket. But how do you not realize you’ve lost a shoe?”

Dear Reader, I will tell you what I told him: I am as perplexed as you are.

All I know is this: It wasn’t until I hopped into my friend’s car—or was it a cab that we squeezed into?—that I fully realized I was heading home with one less shoe than when the summer evening began.

To this day, the mystery of this funny memory—a memory that feels like a dream, though I
swear it happened—remains unsolved.

L and I came close to dating but somehow never did. The romantic in me wants to think she scooped it up. Reversed roles live action Disney before live action Disney was a thing. But, of course, we already knew each other well.

And as my son says, “Dad, no one would want your shoe.”

I’m sure he’s right.