August 11, 2003 12:00 PM

After decades of feeling she had been born the wrong gender, Jennifer (née James) Finney Boylan decided to become a woman. A novelist, husband (to Grace Finney, 43), father (to Luke, now 9, and Patrick, 7), and cochair of the English Department at Colby College in Maine, Boylan, 45, had gender-reassignment surgery in 2002. The change was agonizing—and supremely liberating. Does she miss being a man? “I miss pockets,” she says. The following is an exclusive excerpt from her new memoir, She’s Not There: A Life in Two Genders.

I was born in 1958, on June 22nd, the second day of summer. It was also the birthday of Meryl Streep and Kris Kristofferson, both of whom I later resembled, although not at the same time. One day when I was about three, I was sitting beneath the ironing board, as my mother ironed my father’s shirts. “Someday you’ll wear shirts like this,” said Mom. I didn’t understand what she was getting at. She never wore shirts like that. Why would I ever be wearing shirts like my father’s?

Since then, the awareness that I was in the wrong body was never out of my conscious mind. My conviction had nothing to do with a desire to be feminine; but it had everything to do with being female. It was not about whether I was attracted to girls or boys, though. Being gay or lesbian is about sexual orientation; being transgendered is about identity.

What transsexuality emphatically is not is a “lifestyle,” any more than being male or female is a lifestyle. Gender is many things, but one thing it is surely not is a hobby. What it is, more than anything else, is a fact.

After I grew up and became female, people would ask me, how did you know, when you were a child? This question baffled me. Remember when you woke up this morning—I’d say to female friends—and knew you were female? That’s how I felt. That’s how I knew.

Sometimes I’d go into the room next to mine and put on some old dresses. I’d stand around thinking, why am I doing this, and then think, because I can’t not. Then I’d take the dresses off and think, you’re an idiot. Promise you’ll never do that again.

Boylan hoped love might cure her, and when she fell for Finney while in grad school at Johns Hopkins in 1987, she felt it had. The pair wed and moved to Maine. But by 1998 Boylan had told Grace about her gender confusion.

Grace was strangely tolerant of all this. Of course I hadn’t said that I was transsexual when I came out to her. I told her what I hoped could be true, that expressing just this much of myself through occasional cross-dressing would be enough. Sometimes Grace would come home to find me en femme, and she’d just shake her head and laugh. “No pearls before five,” she’d say.

Visiting Amsterdam in 1999, I went out in the world for the first time wearing a skirt. I spent hours getting ready, shaving my arms, my legs, my face. My makeup was perfect. No one looked at me twice.

When Boylan realized she had finally gone as far as she could as a man, she sought a therapist’s help.

“You know what hormones will do, don’t you?” my therapist said. “Your skin will soften. The hair on your arms and legs and chest will grow finer. Your breasts will start to grow. Fat will move toward the female places–your bust, buttocks and hips. Above all, the changes hormones will bring are emotional.”

“I can’t do this to Grace,” I said.

“You aren’t ‘doing’ anything,” my therapist replied. “You are a transsexual. You have managed to carry this burden all these years. It is time for you to get help. Grace is a social worker; maybe she will understand.”

That evening, just before sundown, Grace was in tears, her heart broken in two.

Within months Boylan began feeling the effects of the hormone regimen her doctor had prescribed.

When people asked me, later, what the effects of the pills were, I cleverly said, “The estrogen makes you want to talk about relationships. The antiandrogen makes you dislike the Three Stooges.” My moods began to shift capriciously. Testosterone had given me a sense of protection, of invulnerability. This new world seemed to have no buffers. Things which used to just bounce off me now got under my skin.

No issue was as hard to resolve as the issues around food. I was tall and slender. And yet, when I went out, I would hear myself ordering diet soda, or asking for the spinach salad. I started weighing myself constantly.

Boylan explained her situation to surprised but supportive colleagues and friends. Telling her kids was immeasurably harder.

“Have you noticed that I’ve been looking more and more like a girl?” I said [to Luke one day].

“Some of my friends think you are a girl,” Luke said.

“That must be hard for you,” I said.

“I just tell them, that’s my daddy.”

“Lukey, I need to talk to you about something. I have a condition that makes me feel like a girl on the inside, even though I’m a boy on the outside. Does that make any sense to you?”

“Sure,” he said.

“So I’m taking medicine that is making my outsides be more like a girl. After a while, I’m going to totally be a girl. I know that might make you sad but it’s what I need to do.”

“I won’t be sad,” he said. “You’ll still be you.” A few weeks later, my children came up with the name “Maddy” for me—their combination of “Mommy” and “Daddy.”

I shifted genders so slowly around my children that when I finally appeared before them wearing a skirt and makeup they hardly noticed. Luke looked up and said, “Hey.” I said, “Hey what?” And he said, “You’re not wearing your glasses.”

After two years on hormones, Boylan scheduled gender reassignment surgery at a hospital in Wisconsin. Then she had a wrenching talk with Grace.

“Do you believe,” I asked slowly, “that all of this is necessary for me?” She wiped her eyes. “I suppose so,” she said. “But no matter what happens from here on out, I lose. I would never keep the person I love from being who she needs to be. But I can’t be glad for you, Jenny.”

The next day, as I took a long walk, I realized I would never regret being female. But I would probably always regret not being Grace’s husband.

Like many transsexuals, Boylan felt her sexual orientation shifting once she changed genders.

Looking around at the world, I would occasionally think, jeez. Look at all these men. It was inevitable, I suppose, that Grace or I, at some point, would take a step in a new direction. I think we both dreaded the moment as much as we hoped for it. Where would either of us find men that we adored as much as we had adored each other?

A few months after my surgery, Grace and I attended the wedding of a friend’s daughter. During the reception, Grace turned to me.

“Jenny,” she said softly.


I had no idea what she was going to say next. I want you to move out…I want a divorce…. Nothing would have surprised me. With the exception, perhaps, of the one thing Grace did say to me then. “Jenny,” she said. “Do you want—to dance?”

For a moment I didn’t know how to respond. Then I said something I had said to her a long time ago, in the National Cathedral in Washington. I said, “I do.”

Along with their love for each other, their two sons provided a reason for staying together.

“Tell me something, Luke,” [I said one day]. “Don’t you ever feel bad, not having a daddy like other kids?”

“Yes,” he said.

“I’m sorry,” I said. “I know it’s not easy, having me for a parent.”

“I don’t mind,” he said. “I like you this way.” He climbed into my lap and hugged me. “I love you, Maddy,” he said.

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