Jake and I dated in college. I noticed him because he was extremely well dressed and looked like he stepped directly out of a Ralph Lauren ad. He liked me because I had those very 90s Gucci sunglasses and wrote strange poems. We got together rather quickly and were soon never apart. I was pleasantly surprised to have found a boyfriend with a family even more cringe-inducing than mine. At the time, his mother was having an affair with a married man. Not separated. Married. His sister was an anti-social artist who stayed in her room all day painting. I loved them for, not in spite of, their madness. The only problem with coming from a crazier family than mine is that you then turn out even more maladjusted than I am, if that’s possible. Consequently we fought a lot. He thought I was needy. He had a point. I thought he was a little square, which was also true.
However, my friends were all jealous. He was seemingly perfect. Tall, nice and exceptionally good looking with sad brown eyes. He had gone to a fancy East Coast boarding school where he played lacrosse. But it wasn’t just looks that drew me to him. We both loved to read and had many favorite books and magazines in common. But we really bonded over a mutual love of fashion. We’d flip through Vogue and he would fantasy-dress me. “You’d look good in that,” he’d say, pointing to a dramatic, off the shoulder Badgely Mischka gown. “It’s seven thousand dollars,” I said. “When I make $25 million dollars a year I’ll buy it for you in every color.” he promised.
Unfortunately, I was too crazy to make it work. Everyone goes through at least one outlandishly insane phase and this was mine. I did everything I could to sabotage the relationship. When he told me he loved me for the first time, I hung up on him. One day we were hanging out and I noticed his perfectly worn, prep school lacrosse sweatshirt laying out on his bed, so I stole it. Looking back, it was one of my worst phases.
After I graduated, we didn’t keep in touch and I really didn’t blame him. I tried to email him but he never responded. “Maybe it’s because I stole his sweatshirt?” I wondered. From that point on, he was, in my mind, the one that got away. I never forgot him, but his memory grew more distant, until one snowy Friday night in New York City, seven years later.
I had just worked 16 hours a day for three months and was looking forward to a weekend of sleeping. I was deliriously tired and of course the train had tons of problems because the wet snow had messed up the signals on the tracks. As we approached West 4th Street, the conductor announced that the train was out of service and to transfer across the platform. I stumbled out of the subway doors with the rest of the grumpy commuters and as I looked across the platform I thought I might be hallucinating.
There was Jake, in real life. I blinked, looked back, looked away and sure enough it was really him. I stopped breathing. This was a big deal. Jake was someone I had truly loved. I had always deeply regretted losing my mind at the end of our relationship. He was still so handsome, like a modern day Cary Grant. When I saw him, he was having an animated conversation with an old woman about the changing of trains. I walked up to him, in a daze, and tapped him on the shoulder. His face was kind when he looked at me with just a hint of pity. I could live with that. Then he wiped some dirt off my nose, because I am just about the coolest person on the planet and New York City is filthy. When the train came we got on and my stop was the next one, Broadway-Lafayette. Even still we had a nice, albeit brief, conversation about what we were currently reading and he gave me his card so we could get coffee sometime. I took this as a good sign. Maybe he didn’t hate me after all?