The One That Got Away, Thank Goodness

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?

So when I emailed Jake and he emailed back, I was again pleasantly surprised. We struck up a friendly email relationship. I’d send him articles on Iran and he’d send me articles on the new Chloé spring line. We tried to make plans several times but both of us were really busy and nothing worked out. One weekend I had to work, the next he did. Finally about a month into this he called me on a Sunday morning to chat. We were both still in bed and the conversation turned suggestive. “What are you wearing?” he murmured. Ironically I actually was naked since tenement apartments are always inexplicably boiling hot in the winter. But I didn’t want to assume anything about this guy or any potential for us to get back together. I also didn’t want to get my hopes up or participate in this cliché. “I’m um, wearing an old Michigan shirt and some boyshorts.” I lied. We agreed to hang out as soon as he got back from his business trip.

Jake had just come back from working in the Peace Corps in Africa so he was relatively new to New York. I took it as another good sign that he lived just down the street from me on Houston, directly across the street from another old college boyfriend of mine. I couldn’t help but wonder what it meant that the only men I ever loved lived directly across the street from each other. I’m not a big believer in “meant to be” but this seemed like it was going in that direction.

One Thursday evening, I came home from work, took off my makeup, got comfortable and ready to settle in for the night. I figured I would multi-task; eat dinner, watch my favorite television show and text Jake to set up my weekend of what would surely be a passionate reunion with the love of my life. I sent him a text just as the show began asking him when he wanted to get together.

Almost immediately, an unknown number called my phone but the other line was silent. “Hello?” I said, again and again. Just as I was about to hang up I heard a voice. “Caitlin? It’s Jake,” he said, rather frantically. I laughed. “It’s customary to say hello,” I reminded him. “Sorry, my cell died. What’s going on?” I told him I wanted to see what he was up to over the weekend; maybe we could get coffee like we had talked about. I wanted to start small. This had all been very organic and I didn’t want to mess anything up. Jake was breathing funny and very eager to hang out. “Do you want to hang out tonight? We can go to my place right now!” he said.

He was acting peculiar but I let it go. We’d had so many phone dates and emails and texts that I figured maybe we could start up our relationship again without the usual formalities of courtship. We did have a history after all. I decided to skip my favorite show and got out of my comfy sweatpants, re-did my hair and makeup and agonized over my outfit choices to go back out into the cold New York City night. After all it had been so long since I had connected with someone and I thought maybe the chance encounter with Jake was, egad, “meant to be.” This was a cliché I could live with.

When Jake opened his door, I almost fainted. The smell hit me like I had been punched in the nose or accidentally eaten too much wasabi. I had forgotten he didn’t wear deodorant. “That’s right, he wasn’t perfect,” I thought to myself. I could not believe I blocked that detail out. He was a total prince in my mind. Since college, his body odor had gotten much worse. My theory is that he’s too hot for anyone to mention it. The combination of the years of no deodorant, along with living in Africa, had resulted in new, particularly pungent, strains of bacteria growing in his armpits. It reminded me of the stench of rotting chicken soup, like that time I forgot to clean out my lunchbox on the last day of second grade, only to discover that same lunchbox in my backpack the first day of third grade. Those kinds of smells burn their way into your psyche and never leave.

When I walked in, I had to hold my breath. My eyes watered. He looked great though. He was wearing a Helmut Lang cotton shirt I recognized from the latest issue of Nylon and artfully tattered jeans.

We sat on his modern couch and talked for a while about what we had been up to since college. We were getting reacquainted and I honestly didn’t feel like he hated me, which was a nice surprise after all those years. Then he put his hand on my thigh and I didn’t know what to do. I thought I would be more enthused but it seemed out of place. Next, he lay down and put his head in my lap. Last time I checked, this is not a platonic gesture, but I went along with it. We continued our conversation while I stroked his hair. All of a sudden he sat up and asked me if I wanted Chinese food. I hadn’t been thinking about it but sure, why not? I said yes, thinking we would order in or go out. Jake ran over to his kitchen and proceeded to get out old take out and heat it up for us. As I sat there watching him, I knew something wasn’t right. I was freezing all of a sudden and wrapped my scarf around my shoulders.

We ate the leftovers at his counter. Reality was not matching the fantasy of the kind of glamorous reunion I was hoping for. When Jake got a phone call he took it privately in his bedroom. When he returned he had a strange grin on his face. Apparently his “girlfriend” Amanda was going to have a houseguest that weekend and she wanted to see if the guest could stay with Jake. “So I told her,” said Jake, “why don’t you stay with me and your guest can stay at your place.” How long had they been together, I inquired. He said they’d been together for six months. My serotonin levels plummeted. I felt like I was going to faint. My vision wavered and my neck felt funny. I made the executive decision to get out of there. I got my coat and excused myself.

We said we’d meet up for coffee some time soon. I cried as I walked home down Houston Street. Why couldn’t we have just gotten coffee to begin with? Why was “Amanda” never even mentioned, if in fact she did exist? And if he had a girlfriend, why did he put his head on my lap just twenty minutes ago? Rejection happens but this time it hurt worse. I had gotten my hopes up against my better judgment. I could understand why Jake hated me but why would he go through all those emails and phone calls? I hate plenty of people and call me old-fashioned, but I avoid them. It’s a lot easier than being vengeful.

I saw Jake on the subway a few months later. We were reading the exact same issue of The New Yorker and sitting directly across from each other. I only noticed him when the train car emptied. We looked directly at each other and then back down as though we’d never met. I may not have yet come across a love interest that’s “meant to be” but I have managed to acquire plenty of wardrobe staples that are. More than anything I’m just glad I stole that Exeter Lacrosse sweatshirt of his back in college when I was crazy. I still get tons of compliments on it.

Image by author