ahh, young love

Here's a riddle for you: I lost my virginity to a woman, but I've never been gay (well, not in any way that really counts). So, figure that one out.

I'm referring, of course, to my old boyfriend who became a woman. I've eluded to this now and then, and Darren inadvertently inspired me, as he so often does, to tell the whole story.

Let's call him Chris, shall we? I feel like he deserves a pseudonym; it's bad enough that if you add an "e" to the end of his actual name, it makes a girl's name.

So I met Chris in eighth grade when he moved to Melonberry (Mark's nickname for my hometown) and was put in my lab group in science class. I was happy because he was cute and tall and new. I wrote in my diary, "I have a crush on the new boy. He's from New York." He liked one of my friends, who looked, no kidding, like a young Heidi Klum (and now just looks like Heidi Klum). And then, I don't know, eighth grade ended and I didn't really pay much attention to him again until junior year of high school, when we had a bunch of mutual friends. He was funny and smart and played football, which meant I was bound to have a crush on him sooner or later.

Now is probably a good time to tell you what most of my friends know all too well: I am ridiculously specific in what type of guy I'm attracted to. He has to be big. Not big-big, but Jason Varitek big. That's the best (albeit extremely Bostonian) example that I can give you. When I met Steve years ago, it was a good thing he liked me too because I probably would've had to climb on top of him regardless. Party Jen and I spent a couple nights in Mexico hanging out with the Armenian mafia (don't ask); I ended up getting paired off with one of them but I preferred his friend, whom they called Big Jack. He had no personality but he was perfect in his bigness. I actually tried to rationalize to Jen why it might be okay to ask my guy if he'd switch with his friend. If boy-swapping on vacation is wrong, then damn it, I don't want to be right!

My point is that Chris was big and very guy-ish (oh, the irony), so it was only a matter of time. He was dating one of my friends, who over the years had morphed into Drama McDepressington, pulling stunts like running out of school and down the street because someone had looked at her the wrong way. (I feel compelled to put in a disclaimer that she was probably legitimately depressed and I hope she's okay now, but at the time she was all over the place and it was more than any of us knew how to deal with.) Chris and I initially bonded over what was going on with her and how we could help, and then she started pulling away and becoming friends with weirdos from another town, and he and I just became friends in our own right. We had a radio show together at the school station on Thursday nights, he taught me how to drive on highways, and we just hung out all the time.

After graduation, he and Drama broke up, and then he and I were together. Even now I still have the wooziest, giddiest memories of that summer after senior year; I was just on a cloud the whole time. We thought this was IT, we decided we'd get married, the whole nine yards. Needless to say, I was ready to break up with him basically my first week into college. So began the cycle of dysfunction: He'd call and I'd be out and he'd get insecure, and then it was the old song and dance... the more needy and hurt he became, the more I pulled away. But then I'd come back to Melonberry on school breaks and he'd be there to occupy my time. I should've just ended it completely, but we went back and forth like that for the next two years.

Then I finally broke up with him during my junior year, in the parking lot of my dorm. I used a line from a song by Jackopierce, which of course he never knew, thank God, but how ridiculous is that? Then I went inside and basically had an impromptu party with my friends; tacky, I know, but it was a huge relief. He called me the next day and told me how everything that had gone wrong between us was his fault. I didn't want to even hear his voice; we just needed to leave each other alone for awhile.

Three or so months later, we reconnected and sort of became friends again. I knew he was over me when he explained to me how everything that had gone wrong between us had actually been MY fault. Hmmm. Anyway, we were never friends again like we used to be (nothing like a dysfunctional relationship to take the fun out of a friendship), but we still hung out sometimes.

Then I was home for the summer after my junior year, and I had dinner with a friend who had just graduated from high school. He told me that a girl in his class was getting a sex change as a graduation present from her parents. I vaguely remembered the girl and I'd never heard of anything like this. When I got home, I called Chris.

Me: You'll never believe this! I just had dinner with Jeff, and he told me that So-and-So is getting a sex change for a graduation present!
Chris: Oh.
Me: She's BECOMING a MAN!
Chris: Yeah.
Me: Is this not UNBELIEVABLE TO YOU?
Chris: I guess so.

After we hung up, I figured he was just being moody. Then he called me back.

Chris: There's a reason I didn't react to your telling me about So-and-So.
Me: There is?
Chris: It's because, well... I'm a transsexual.

Silence. About a YEAR of silence.

Me: What?
Chris: I'm a transsexual.
Me: What?
Chris: Yeah.
Me: What does... what?

So, yeah. What a way to find out, huh? I mean, what are the odds that I heard this random story and called him to revel in its weirdness, and it turned out to be his deepest, darkest secret?

This was eight years ago, and I can still hear him saying those words to me. Even my friend Dave, who never even met Chris, told me recently that my telling him "I just talked to Chris and he told me he's a transsexual" is permanently embedded in HIS brain.

We were still friends after that, but then he told me he wanted us to get back together, and... I don't know. This was someone I truly cared about and I don't doubt that this was a massive struggle for him and who knows where it all came from. The situation is altogether heartbreaking. But it was not for me to date.

And you know what's funny? A few months ago, when I didn't see him at our ten year reunion, I became compelled to find out what the hell had happened with him. I ended up finding his blog. And yeah, he's a she.

She posted something recently about a band that she was going to see and how the last time she'd heard them had been with me. I didn't remember and posted a comment asking her to refresh my memory. She commented back and told me that while we hadn't actually seen the band together, they were playing at a place near my college one time when she was visiting and she remembered hearing the music. Then she said that the day after, she drove home wondering who I was and what I'd done with her friend.

Seriously? Suddenly I remembered all the whiny voice mails and guilt trips from forever ago. I read that blog entry and then found myself saying out loud, "Fuck that shit."

Yup... we may be almost thirty, but turn up the Stone Temple Pilots, because this is definitely like being 17 all over again.