The Boy I Kissed the Most

I've always described Tyler as the boy I kissed the most. I knew he liked me as soon as he stopped putting ice in his milk. It was my freshman year of college, and we'd meet for lunch every day at the dining hall. I laughed at him for putting ice in his milk and he stopped.

Then one day he took me to his dorm after lunch and we kissed. We'd kiss for four hours at a time all over campus: his dorm room, my dorm room, the study lounge. He never pushed me for anything more, not that I had ever done anything more at that point in my life. It was as innocent and respectful a make-out session could be.

One afternoon we stood up from whatever couch we were making out on and Tyler popped a zit in the mirror. I didn't want to make out with him anymore.

***

I saw Tyler next standing outside my English building. He was wearing yellow and white camouflage pants. I'll never forget those pants. They were hideous. I thought of the zit popping and the yellow camo pants and knew I made a good decision in not kissing him anymore.

He stood on the sidewalk and told me he was going home. Taking a semester off. People don't take a semester off college; they drop out. I wished him well, thinking I would never see him again.

***

A year later my very first boyfriend dropped me off at the English building. There stood Tyler. The time off served him well. He got his act together. He got cute, very cute. He told me he was back on campus and joined a fraternity. I think I stuttered. The boyfriend noticed and later grilled me on it.

***

There he was again at my job. The largest employer of university students was a telecommunications company that used us for telemarketing. We had both worked our way to supervisors.

Tyler was everywhere. And this is the thing: we never talked about the making out. I wondered if he even remembered about our freshman year together.

***

We both ended up in the city. Tyler reconnected over Facebook instant message. His profile revealed that he had the same girlfriend since college. It had been four years and they were doing the long-distance thing. I always invited him out to meet up with our mutual friends Harvey and her husband, but he never actually made it out.

***

Two years ago I was at happy hour with old coworkers and I kept staring at the boy in the next booth. I leaned to a girl, "That looks like the boy I kissed the most."

Tyler made eye contact and waved. I jumped booths and caught up with him. He was a triathlete. I was just getting a hang of running.

***

The next time I saw Tyler was on purpose. The local chicken place that everybody loved in college was opening a store in the city. We made plans to eat there together on the opening night. We talked about triathlons. We talked about running. We never talked about kissing.

***

Facebook revealed that Tyler and his girlfriend broke up. He IMed me late one night, asking that I come over and cuddle since it was so cold. He added as an afterthought that he wasn't into dating at the moment. I declined. I was into dating and not hooking up.

***

Tyler IMed me this week. It's been a year or so since we last communicated. He asked me about my life: my work, my friends, my relationship.

He's asking me so many questions that he's wanting me to ask him the same, I thought. So I did.

Tyler was vague. He said he was undergoing some big lifestyle changes. He's laying the foundation to transition.

"Like what?" I typed. "You going to marry your girlfriend of the last year?"

"Maybe I will get married one day," he wrote. "But not like you think."

He obviously doesn't want me to know, so I'll just drop it, I thought.

"Actually, the transition I was talking about is becoming female."

I stared at the words. Frat boy Tyler? The triathlete who always has a girlfriend? Who currently has a girlfriend? Clearly he's messing with me.

But... just in case. I'd rather be sensitive and take him seriously and have him go "Just kidding!" over not taking him seriously when he's trying to tell me something.

"Seriously?"

"Yes."

I re-read his previous statements. "Laying the foundation to transition." He was being serious.

I told Tyler that he was brave. I told him I would always be his friend and I would always support him. This excited him. He wanted to meet in person and introduce me to his alternate self. He started to go into details about how he's been cross-dressing for years. He's even dated men as a woman.

I leaned back into my chair at work and felt my brain explode. Clearly I would not be working the rest of the day. Tyler's always dated women. Tyler still looks like a frat boy. We made out!

I don't know why Tyler told me. I guess it's because we've known each other for 12 years and have always been friendly without being too close. If I never spoke to Tyler again, neither of our lives would change. He wasn't losing anything by coming out to me.

***

I've never had anyone come out to me before. There were people whom I knew were gay before they came out to the general population, but I've never had anyone sit me down and come out to me.

The only experience I've had with trans people have been related to city life. It's not uncommon to walk into a Walgreens in midtown to refill a prescription and wait next to a man dressed in Lycra, a wig and acrylic nails. I can't believe that's Tyler now.

I find myself searching the recesses of my mind for what I know about this. Transvestite is different than transgender. J. Edgar Hoover was a transvestite. Just because you're transgender (or transvestite) doesn't mean you're gay.

I don't know if Tyler will keep his girlfriend after the operation. I don't know if he'll date men. He did say she wasn't aware of the full extent of his intentions. His family doesn't know. He's a woman at work.

My brain explodes all over again. I'm reliving every interaction we ever had and am searching for indications that Tyler wanted to be a woman. The times we made out, he never pushed further. Was it because we were both young and I, at least, was a virgin? Was it because he knew then? Was this why he was in a long-distance relationship for so long, so he could be straight in pretense? When we ate at the chicken restaurant, he told me a female teacher wanted him and he wasn't really interested. Was it because he was dating men at the time? As a woman?

When he asked me to come over that night, that was after all of this started for him. I said no. Kaboom.