At a back table in the dimly lit French restaurant, I tried not to smoke yet another cigarette.
"More wine?" my waiter purred, gliding up with a bottle of Cabernet. Without waiting for an answer, he filled my glass for the third time. My stress, I realized, was showing.
I was jumping out of my skin. It wasn't just that my "date" was a half-hour late, or even that he was also an ex-boyfriend, who I would be seeing for the first time in eight years. The reason was that, in those eight years, Jean (not his real name) had decided he was no longer happy being the man he was. Tonight, for the first time, I'd be meeting my old boyfriend in his new incarnation: woman.
He'd contacted me by phone a few months earlier, for the first time since we'd parted ways back in 1989. We'd fallen completely out of touch after breaking up, so I'd been startled to find a message from him on the answering machine. His voice sounded odd and breathy on the machine -- familiar but somehow unfamiliar, too.
"Sarah ... it's Jean," the voice said. "I know it's been a really long time ... but I was hoping we could talk. I've ... been going through some big changes lately."
He'd gotten my number, he explained, from an old mutual friend he'd bumped into on the street. Immediately, I called this friend to find out more.
"Jonathan," I said, "why does Jean's voice sound so weird now? What kind of 'changes' are we talking about here?"
Jonathan sighed.
"I know, I should have called and warned you," he said. "I just didn't know how to tell you. Sarah, he looks different. He looks ... not like a girl, exactly, but ... kind of half like a girl."
"What do you mean?" I cried. "Which half?"
"No, no," said Jonathan. "I mean, he sort of looks ... like he's in the middle of some sort of metamorphosis. Like he's started the process of becoming a girl. But he's not totally there yet, I don't think. I don't know. I'm sorry -- I was too weirded out to ask."
I hung up feeling fearful and deeply unsettled. How could it be that someone I'd known so closely -- someone I'd slept with, for God's sake -- was undergoing something as massive as a sex change? And how would I deal with this change if I started corresponding with Jean again? He was someone I had warm, loving and respectful memories of, one of the few early boyfriends I could truly say I had no regrets about.
I wanted to think I'd be able to relate to him compassionately, the way I had with other friends who had gone through life changes such as parenthood or conversions of faith. But Jean's transformation was much more disturbing than those. I'd known him, and loved him, in a certain way -- as a man. If he was changing that, it was almost as though he were taking something away from me.
There had been warning signs. Jean's unhappiness with his sex had surfaced as early on as our sophomore year in college, when we'd been sweethearts. Halfway through our nine-month relationship, we'd moved into an off-campus apartment together; he was the first man, other than my dad, whom I'd ever shared a living space with.
Our first few months in the apartment were a blast. Jean was brainy and creative and funny, a digital whiz who loved to compose music on his synthesizer keyboards, and who was into e-mail years before most people even knew it existed. At night, after classes, we'd cook together, then eat ice cream while watching old reruns of "Miami Vice" on TV. The sex was great -- Jean was adventurous in bed, and had a broad-shouldered, 6-foot-tall body that I found very attractive.
But living together makes it hard to keep secrets. One night, after smoking some particularly potent marijuana, Jean admitted to me that he'd always felt like a part of him was "feminine," and that he sometimes fantasized about being a woman when we made love. I was taken aback by these admissions -- I had never considered Jean anything but manly -- but I did my best to put my worries aside. After all, I reasoned, who was I to judge? It wasn't as though I didn't have any sexual idiosyncrasies of my own. And, from what I understood, people's habits inside the bedroom didn't necessarily extend outside of it.
But once Jean had made his initial confession (and found that nothing terrible came of it), the floodgates flung open. He began spending hours a day in primitive computer chat rooms, and a stack of transsexual porn magazines appeared at the back of our closet. Sometimes, I'd come home from school to find that my clothing drawers seemed pawed through; the lipsticks and eyeliner pencils on my bathroom shelf began to look suspiciously worn down.
Because I cared about Jean, I tried my best to be understanding. For a little while, I even tried helping him to "explore" his female side, thinking that doing so might help him temper his preoccupation with it. We spoke openly about his fantasies, played role-playing games in bed; once, at his request, I bought him a pair of large-sized nylons at my favorite lingerie store.
But my heart wasn't in these experiments. Deep down, I kept hoping that Jean's fixation with femininity would pass. And when it didn't, I realized that our relationship couldn't last. Accepting as I wanted to be, I also had to accept that my own sexual preferences were pretty conventional: I was a normal, straight woman who wanted an ordinary, masculine man.
I thought about all this as I played Jean's answering machine message over and over in my apartment. My first inclination was not to call back. After all, I hadn't even been able to manage the idea of Jean's feeling like a woman, never mind becoming one. Did he have to alter himself so severely, so permanently? Wasn't there some other way he could come to peace with his body, one that didn't involve a scalpel?
But then I started to think about what an enormously lonely undertaking a sex change must be. I'd known Jean's family, and, loving and tolerant though they were, I couldn't believe they'd be able to accept their only son and brother this way. If my phone conversation with Jonathan was any indication, Jean's friends weren't adapting to his physical changes very well, either. Dating and romance must be, at the very least, difficult; and then there was the worst part -- the fact that, in order to be doing this, Jean must have felt desperately wrong in his own skin. It didn't matter if I, or anyone else, thought he was just fine as a man. He was apparently willing to go through almost unimaginable difficulties not to be one.
It was this last realization that made me change my mind about calling him. I couldn't promise Jean, or myself, that I'd be able to handle things any better this time around. But if he had been able to muster enough bravery to do what he was doing, I could damn well be brave enough to pick up the phone.
"So ... how are you?" I asked, once we had gotten past the awkward, preliminary it's-so-good-to-hear-your-voice-again stuff. (His voice, I realized, wasn't all that different than it had been before -- just about a half-octave higher.)
"Well," he said, with a little giggle, "I'm an A-cup."
I nearly dropped the receiver. A sudden image of Jean as I'd known him, bare-chested, with a towel around his waist and shaving cream on his chin, flashed in my mind. The idea of cup size did not jibe, not in any way, shape or form.
"Uh," I said, trying to sound casual, "wow. I mean ... already, huh?"
"Mm-hmm," he replied. "I started the hormones three months ago, so they're still ... developing. But they're getting bigger every week!" He giggled again. "Soon I'll probably be bigger than you!"
"Oh ... well, that wouldn't be saying much," I said faintly. My head was spinning.
Jean was silent for a moment.
"Look," he said, finally. "I'm sorry. I know I'm probably throwing this stuff at you too fast." I noticed myself nodding.
"It's just that it's exciting for me, you know? And ... I don't really have many friends I can talk to about it. Please don't be mad."
"Jean, I'm not mad at you," I said. "You just have to remember how hard this is for me, OK? We have to go slow here."
"Slow is good," he replied, sounding relieved. "Slow I can do."
"OK."
"OK," Jean said, a note of mischief in his voice. "So, tell me about the men in your life."
It took a month's worth of phone conversations for him to convince me to meet again in person. In that time, I got reasonably comfortable speaking to Jean from the haven of my own living room, where I could concentrate on his still-familiar voice without having to see how he'd changed physically. The distance helped; as we talked, I found I was able to put my squeamishness aside and ask him more and more personal questions about his transformation. I found out, for instance, that though he still found women sexually attractive, he had recently started dating men, too, because they helped him to feel more feminine.
I also learned that his family, and most of his older friends, had indeed disowned him since he'd begun to change physically, and that he'd started doing freelance consulting work from his home, so as not to make co-workers feel uncomfortable with his "in-betweenness." Over the phone, I was even able to talk to Jean about the "final cut," which would complete his womanly transformation -- a step that, he said, wouldn't be happening until he'd been taking the hormones for at least another year.
Of course, I understood that it was the acceptance and approval of his new body that Jean needed the most. The reason he kept badgering me to meet him was because it was a test -- a test I would have to pass if I really wanted to be his friend again, and one that most of the other important people in his life had already failed.
Eventually, I agreed to meet him for dinner one night at a French restaurant in New York's West Village. If I was going to see him sooner or later, I reasoned, better to do it sooner, while he was still a work in progress.
"What should I do?" I asked Jonathan, once Jean and I had set the dinner date.
"Get drunk," he advised.
"Before, during or after?" I said.
"All of the above."
The evening arrived. It was probably just displacement of my anxiety, but I had a terrible time deciding what to wear. I automatically donned the same black cocktail dress I always wore when a man took me to a nice restaurant. But then, as I stood half-clad in front of the bathroom mirror, a mascara wand in one hand and a Budweiser in the other, I was struck by a sudden fit of self-consciousness. Jean certainly wasn't just a guy anymore -- he would now be looking at my appearance with a woman's scrutiny. Was my ensemble too plain? Maybe another piece of jewelry, or a scarf ... or would that make it seem like I was trying too hard?
After an hour of deliberation, and two more beers on an empty stomach, I finally tottered to the restaurant. The maitre'd promptly seated me at a quiet table at the back of the room, and I lit the first of many cigarettes.
What was the worst that could happen? I tried to imagine Jean flouncing through the door of the restaurant in a RuPaul-ish feather boa and shimmery gown, batting inch-long false eyelashes at me from beneath the tendrils of a platinum wig. Then an even worse picture entered my mind, the picture of a pathetic-looking drag queen I'd seen once in Provincetown, with huge feet stuffed into tiny kitten-heeled pumps, and hairy arms dangling from a dressing gown that might have belonged to Blanche DuBois. His crudely applied makeup had looked smeared, as though he'd been crying.
I drained my wine glass. I'm being ridiculous, I thought to myself, as the waiter refilled my glass again. I'm being ridiculous because I'm afraid.
Then I glanced toward the door.
Immediately, I understood why Jean had arrived so late: he wanted to make an Entrance. He slowly unwound a gauzy black scarf from around his shoulders, pulled off his black gloves one finger at a time, and allowed the maitre'd to kiss his hand before starting back toward my table. He had a new walk, I noticed -- not an overly feminine sashay, but a certain cant of the hips that suggested womanliness. For a split-second, I let myself wonder about the source of this gait: Could it have come to Jean naturally, as a result of his new female hormones? Or had he studied other women, practiced in front of a mirror?
As he made his way toward me, people at the other tables glanced up, then went back to their meals; to them, Jean probably looked like just another woman -- albeit a tall, strapping one -- passing by. He wore a simple black suit, black nylons and his curly blondish hair was long now, and carefully arranged in a French twist.
"Hi," he said, breathlessly, once he reached the table. He stood for a moment, clutching his velvet purse, and looked shyly down at me. His nails, I saw, were longer than mine and manicured, his makeup artfully, but not overly, applied. In the soft light, I could see no trace of the razor stubble that used to shadow his face when we were younger. I drained the last of the wine from my glass and stood up.
"You look so pretty," Jean said, and held out his arms for a hug. I moved in and embraced him. It was utterly bizarre, that hug. His height and the strength of his arms felt the same as I'd remembered, but I could smell his perfume now, and could just barely feel the place where his new breasts rested against me. Oh, God, I thought suddenly, this is too weird. I can't handle this -- I should just leave. But when we moved apart, I continued to stand there, swaying slightly. Glancing nervously at Jean's face, I could see that he needed something; there was a question glittering timidly behind his shadowed eyes.
I knew exactly what it was. Can I do this? I asked myself. Can I at least try? Yes, I could. Strange as it was, I could tell this old-new friend of mine what he needed to hear -- because it was true.
"You do too, Jean," I said, smiling at him. "You look pretty, too."
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