Women I dated, when I was a man

I kept hoping love would transform me. But, secretly, I longed to be female


Jennifer Finney Boylan
July 2, 2009 2:24PM (UTC)

With Maeve it ended with a big fight. This was back when I was still a man. "I never know what you're thinking," she said. We were at a bar in Baltimore, eating potato skins. "I mean, what the fuck. Who are you, anyway, when you're out of my sight?"

Maeve was in my fiction workshop at Johns Hopkins. It was becoming clear to me that she was a realist, not only in her writing, which was fine, but in her life as well, which was where the trouble came in.

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I finished my pint. "Why can't the truth be about this, instead?"

"About what?"

"About making each other laugh. Telling stories. Singing songs. The blarney. That's so wrong?"

She was looking around the bar, as if she'd already decided it wasn't too soon to start shopping around for another boyfriend. "You know," she said. "Sometimes you're a real asshole."

Afterward, I went back to my apartment on the corner of Maryland and 29th Street, locked the door, pulled down the shades. I got out the cardboard box that contained all my stuff, put on the bra and hose, the blue sweater, the black skirt. Did the makeup, too, although I didn't like makeup. I thought it made me look fake.

The wig was last. It made me look kind of like a run-down Joni Mitchell. Then I walked back out to the living room and sat down on my black leather chair with a copy of an anthology entitled "The Major Poets," edited by Coffin and Roelofs. I was reading a lot of Keats back then. It was our man's theory that truth was beauty; beauty, truth. It was nice to think this might be true.

I looked at myself in the mirror above the parlor fireplace. I didn't look so terrible. Most of the time, when I went out en femme in Baltimore, you wouldn't know I was reprehensible unless you looked real close.

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I always passed well, maybe because of the slender bones. I could go from the world of men to the world of women at the drop of a hat, and no one was any the wiser, or for that matter, dumber. It was terrifying and amazing, having a secret identity. It was like I was Clark Kent and Lois Lane, all my own damned self, both the experiment and the control.

I thought about Maeve and the fight we'd had in the bar. I felt bad for her. She wasn't wrong about me, either. Sometimes it was hard to know what I was thinking.

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When it came to the women I dated before I transitioned, there were all sorts of ways of ending things. There might be a big fight, one of those calls where I would slam down the phone, and then it rings again three minutes later and you keep on like that all night long. Or I could write a letter, saying I just wasn't ready. I was too immature. Make it sound like I was doing her a favor. Which, of course I was, but not because I wasn't ready. It was because she and I were, you know, same same, not that I could possibly ever explain that.

It was tempting, of course, to try to put it all into words. Usually people assume that the reason you want to change genders is because you are, deep down, kind of an asshole, or that you hate yourself, or that you are actually gay and just don't know it, or that you can't figure out a way of being feminine in the culture while still being a man. None of that had anything to do with it, though. Even now, I occasionally meet trans people who say: Oh I'm a woman too! I love to make cookies and play with dolls! To which I want to wearily respond: Jesus fuck, if you want to play with dolls, play with dolls. You don't need a vagina for that.

But most of the time I've had to resign myself to the fact that people who are not trans will never get it. Why should they? They've never had to think about what gender they are. If you're not trans, you're free from thinking about what gender you are in the same way that white people in America are generally free from having to think about what race they are.

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The women I knew, for their part, liked the fact that I had a feminine streak, that I seemed to be sensitive and caring, that I didn't know the names of any NFL teams, that I could make a nice risotto. A lot of straight women love a female sensibility in a man, an enthusiasm that goes right up to, but unfortunately does not quite include, his being an actual woman.

The romances didn't last, of course. Because, let's face it: I was keeping the basic fact of myself camouflaged. How are you supposed to fall in love when you're so frequently lying?

But I still believed, on some fundamental level, that love would cure me. That if I were only loved deeply enough by someone else I could be content enough to stay a man. It wouldn't be my authentic life, but it would be all right. Anyhow, my authentic life meant coming out as transsexual and taking hormones and having some repulsive operation and please. My authentic life wasn't very appealing. And so I allowed myself to be lifted off the ground by the levitating properties of romantic love. It was a nice effect. Of course, nobody really gets cured by love, but then transsexuals are hardly the only people who believe that romance will lead them outside their selves. We all believe this, at times, even if this belief turns out, in the long run, not to be true. You can't fault a person for hoping that love will make her into someone else, someone better. The world is full of false hopes, most of them dumber than the hope of being transformed by love.

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Then there was Dora, who had a green streak in her hair. This was back at Johns Hopkins. Dora was a writer too. She said she liked my prose. She said it had "a kind of felicity." This was funny, since Felicity was one of the names I privately used to describe myself, not that it ever really stuck. I kept thinking that if only I could find the perfect name for myself, my true name, I would somehow emerge from the shadows and be real. Jenny, for what it's worth, was a name I kept coming back to, then rejecting. It sounded like the name you'd give a donkey.

Dora and I made out a bunch of times but didn't get anywhere near actual sex. Most of the time, it wasn't actual sex I wanted. Like a lot of male-to-female TSs, I was attracted exclusively to women. But my desire was different from the majority of other bepenised individuals, I reckon. I was drawn to women sort of the way you'd be drawn to a fire in a very cold room. Mostly what I wanted to do was to lie beneath the covers and snuggle.

Women liked that, my concern with snuggling. But eventually the fact that the snuggling never went anywhere else just wore them down. What's the matter with you? they'd ask. Don't you want me? I brought my diaphragm. C'mon, let's fuck!

Of course I want you, I'd reply. You're great.

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I reached this point with Dora fairly rapidly, a couple of weeks at most. Then, in order to shake her off the trail, I used a strategy I'd never employed before: pretending I wasn't home.

The doorbell would ring, and I'd know it was her, just from the sound. I'd have to freeze there in my bra, even though the blinds were all down. I'd sit there in my big black chair and try to be completely silent. I figured she'd conclude I wasn't home and leave.

But instead she concluded that I was home and that I was just pretending I was out. So she rang the bell again. This pissed me off. How dare she assume that I was the kind of person who'd actually pretend he wasn't there? If that's the kind of person she thought I was, why was she so anxious to talk to me?

When things got quiet, after a while, the hard thing was knowing the difference between the silence of her actually leaving and the silence of her sitting on the marble stoop. She knew that two could play this game. If I could pretend I wasn't inside reading Keats while wearing a bra, she could pretend she wasn't on the front porch holding a bouquet of flowers and a little card that read, Let's never fight again

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The cards always annoyed me, because of course we hadn't really ever fought in the first place, not unless you consider sitting inside wearing Playtex products while reading Romantic poetry and not answering your doorbell a kind of fighting.

After a while, Dora stopped coming by to ring my doorbell, and I didn't see her anymore. Every now and then, when I was in boy mode, I'd look up from my chair and think I heard something. I'd open the front door and walk out on the stoop, and look around. But she wasn't there.

Rose was the last girl I dated for a long time. I met her at a model-rocket launch some poets were having. On the weekends, Rose transformed herself into an alternate personality, by the name of Scarlett. Scarlett used a teasing comb and a can of hair spray to create Baltimore-style big hair. She wore spandex bustiers, rubber miniskirts, fishnet stockings. She had a pair of ruby slippers, like Dorothy in "The Wizard of Oz." I wasn't crazy about this look. I thought it seemed unnatural.

Rose hung out in a bar called Club Charles, which was across the street from the art movie house, the Charles Theatre. It was a terrible dive, the kind of place where people got stabbed in the bathroom. It was very popular.

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I liked the fact that Rose had another personality, although unlike me, hers wasn't some big state secret. "Why the Scarlett?" I asked her, not because I disapproved, but because if I could figure out why she needed to be Scarlett then maybe I could figure out why I needed to be Jennifer. Or Felicity.

"I don't know," she said. "It's fun being someone else, I guess." I didn't really agree with her on this point. The someone else that I had to be was the person I was almost all the time, this James. I didn't find being someone else any fun at all.

Things got complicated with Rose because she had all these other boyfriends when she was Scarlett, guys whose names sounded like the names of amplifiers, like Peavey and Pignose.

I felt jealous of them, even though Rose and I weren't actually sleeping together. She said it didn't matter what she did when she was Scarlett, because Scarlett wasn't her true self. "What matters, James," she said, "is who I am when I'm with you."

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There were times when I felt that I really loved her.

One Friday afternoon in spring we had a fight about what I called her "split personality." If you really loved me, I said, you'd be just one person, instead of two. Why do you have to have this whole Scarlett thing? It's creepy. I was pretty rough on her, I guess. I made her cry.

What she should have said was, hey, man, she who smelt it, dealt it.

That night I put my girl self together and got into my car and drove down to Fell's Point, the part of Baltimore with the whores and the sailors. There were plenty of she-males on the street too, although I didn't think of myself that way. I just thought of myself as a woman with a unique history. Then I headed up to the Club Charles. 

There she was, at a corner table: Scarlett, her hair reaching halfway up to heaven. She didn't recognize me, which isn't really a surprise. When I was female, I wore contacts. So I sat down at the bar and had a glass of wine. After a while, I noticed that Scarlett was crying. Big mascara streaks trailed down her cheeks. Then she got up and went into the ladies' room.

"What's with Scarlett?" I asked the bartender.

"I don't know, sweetie," he said, shaking his head. "I think she had some big fight with her boyfriend."

Oh for God's sake, I thought, looking at myself in the mirror behind the bar. A run-down Joni Mitchell stared back. I'm not her boyfriend.

I went into the ladies' room. It had a cement floor and a broken window. On the wall were phone numbers, profanities, names of men and women enclosed with hearts. I saw the ruby slippers beneath a stall. I entered the one next to her.

For a while we sat there, on either side of the divider. I could hear her sobbing. "Hey," I said, in a voice that did not sound like the one she was used to. "You okay?"

"No," she said.

"What's wrong?"

"Oh, there's this guy," she said, then stopped to weep some more.

"Tell me about it," I said, but she didn't. She just sat there, behind the wall, weeping. Who knows? Maybe it wasn't even me Scarlett was weeping for. For all I knew it might have been Peavey that had her in tears, or Pignose. I wondered, as I sat there, what I could do for her, whether there were any words I could offer her as Jennifer that I could not speak as James.

"Listen," I said. "I'm sorry."

There was a loud snuff, followed by silence. After a while she said, "What's your name?"

I had never told anyone my real name before.

"Jenny," I said.

"You're nice, Jenny," she said. She snuffed some more, but it sounded like she was descending out of her crying jag now. 

"It's going to be all right," I said. "Really."

"Listen, Jenny," she said. "Can you pass me some paper?"

I tore off some tissues from the roll and passed it to her, under the divider.For a moment our fingers touched, as she took the paper from me. Then they weren't touching anymore.


Jennifer Finney Boylan

Jennifer Finney Boylan is professor of English at Colby College in Maine. Her most recent book is "I'm Looking Through You: Growing Up Haunted."

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