From Best Man to Puzzled Woman

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Modern Love

We took a break after the first set. My friend Laura, the lead singer, and I approached the bar. I ordered a cosmo. She got a Dark ’n’ Stormy. I had been a woman for about a year or two. Everything was still new then.

A sketchy guy approached. He said he liked my hair. Then he asked, “Say, was your daddy a thief?”

“A thief? No, what are you talking about?”

Laura looked on, smirking.

“Well I don’t know, Jenny,” he said. “But someone must have stolen the stars — and put them in your eyes.”

“Why, aren’t you nice,” I said. “That is so thoughtful of you to say.”

“Oh, for God’s sakes,” said Laura, putting down her drink. She grabbed me by the wrist and hauled me off, rather forcefully, toward the ladies’ room.

“‘Why, aren’t you nice’?” she said, incredulously. “‘That is so thoughtful’?”

“Did I say something wrong?”

“Jenny Boylan, what is wrong with you? That’s not what you say to a guy like that.”

I was confused. It had seemed like a nice enough thing for the stranger to say. Although I had grown up and been socialized as a man, since I came out as trans in my early 40s, my friend Laura had made it her personal task to help me negotiate the world of women in which I’d landed.

“It’s not?” I said. “What do I say?”

Laura shook her hands in the air and explained. She said I should make “the old familiar suggestion.”

“Really?” I said. “He seemed nice enough.”

“Oh, Jenny,” Laura said. “What am I going to do with you?”

It was one of the ironies of trans experience that while I had been certain of my female identity since I was 4 or 5 years old, until I finally came out, I hadn’t yet experienced being a woman in the world. I had come to accept that there were some things I’d never get the hang of, like doing a French braid. But worse was that I didn’t know how to deal with men, even though, for almost four decades, I’d been one (sort of).

After all these years, I was suddenly on the receiving end of the male gaze. I had enjoyed — in a facile, superficial way — the validation this gave me, at least at first. But pretty soon, validation had turned to irritation. All at once, it seemed, I had arrived in a world in which men were incapable of leaving me alone.

I had been a feminist before transition, so the many ways in which women are both vulnerable and unsafe in this world didn’t arrive as shocking news to me. But it’s different when it’s you.

It took me a while, but in time I did learn, as Laura had suggested, how to tell off certain men when I felt myself to be in their cross hairs. But if I had gotten used to putting up my shield when it came to the attention of strangers, there was something else that took longer, that in some ways I still haven’t figured out.

This was the way my friendships with men had changed. Some had been my companions since childhood; others I had met in adulthood. But in almost every case, negotiating the difference between a guy-guy friendship and the kind between a grown man and woman turned out to be more complicated than I’d expected.

Take my friend Curly, for example. I had known him since college. A few years after my transition, we had met up in Rome while I was doing an article for a travel magazine. We had visited the Vatican, tossed coins into the Trevi Fountain, and bantered with guys in gladiator costumes at the Colosseum. In the afternoon, I had knelt at the grave of the poet John Keats and wept.

Later, back at the hotel, Curly had turned to me unexpectedly and said that he had “a gift” for me. I hadn’t slept with a man at that point in my life, and given my long history with Curly (I had been the best man at his wedding), I hadn’t realized that this might change.

Curly had given the matter some thought, though. There, in our hotel room in Rome, it became clear that this “gift” was actually something I might do for him. His offer reminded me, in a whole new context, of the lines from the sonnet by Keats: “See, here it is. I hold it towards you.”

I declined. But later, as I lay there in bed listening to him snore, I wondered if, among the male privileges I had surrendered in transition, a certain kind of romance-free intimacy with straight men was the first thing to go. From now on, even among the guys with whom I had been (and in some ways still was) closest, the not-too-far-off aroma of sexuality now hung in the air.

On another occasion, there had been a complication with my friend Rick. We’d been friends since we shared an office at Colby College in Maine in the early 1990s, when we both worked there.

One weekend, when his wife was out of town, I had driven over to his house in Camden to have dinner and talk shop. As we returned from a local bar, we ran into a friend of his, a man I had once known but who did not recognize me now. A day or so later, a rumor began circulating that while his wife was away, Rick had been seen around town with a strange blonde.

“I told them, ‘That was no woman,’” Rick said with a laugh. “‘That was Boylan!’”

I laughed at the absurdity of the situation. But I admit my feelings were a little hurt as well. “What do you mean, ‘That was no woman’?” I asked.

“You know what I mean,” he said, his face flushing.

“Do I?”

If my friendships with straight men had become more complicated, those with my female friends became more intimate. When I went back to my hometown for a high school reunion, I found to my surprise that the most welcoming individuals were the women I had known when I was a boy.

“It’s like I finally understand you,” said Sally, my girlfriend from 11th grade.

It’s fair to say this hadn’t been the case back in the day. In 1974, I hadn’t wanted from her the specific kinds of favors my friend Curly, decades later, would want from me. All I’d ever wanted, then as now, was to be in love.

“It’s so nice,” Sally said, “to have you as a girlfriend now.”

Once, she and I had made out during parties where Grateful Dead albums had played and everyone wound up, at some point in the evening, lying on their backs in a cornfield watching the stars. It had been, as that band once observed, a long strange trip indeed.

My friend Laura retrieved her Dark ’n’ Stormy, and the two of us returned to the main dance floor and talked with Erica, the drummer. Later, we climbed back on stage and played the final set. Afterward, I took apart my keyboards and hauled the amplifiers off the tripods.

Laura’s husband, Tom, the bass player, was disassembling the light show with Jack, the guitar player. I had known those guys for years. We had been men together, after a fashion.

Now, they saw me struggling with my amplifier, an old Peavey that weighed almost 80 pounds.

“Hang on, Jenny,” Tom said, coming to my aid. “Let us carry that for you.”

“I got it,” I said testily, insulted, as if now that I was a woman they considered me a weakling, or worse, someone too incompetent to carry my own amplifier out to my car.

On the other hand, the damned thing was heavy, and estrogen had taken its toll on my upper-body strength.

“Come on, Jenny,” Jack said. “Let us help.”

I put down the Peavey. “O.K. …” I had to admit it was heavy, and they were strong.

“Those are good friends,” said the owner of the bar, watching as the guys headed outside with the amp. Surely, if my friendships with men were different now, there were some ways in which they had changed for the better. Tom and Jack hadn’t really had an opportunity, back when I was a guy, to make their affection for me visible. But they had one now.

“Yeah,” I said. “They’ve always had my back.”

Jack and Tom came back in from outside.

“Thanks,” I said. Erica and Laura and I greeted them, and for a moment we all gathered together in a big hug.

There we were, five friends, men and women. The years had left their mark upon us all. None of us were the people we once had been. But we were still a band.

Jennifer Finney Boylan’s latest book, “Long Black Veil: A Novel,” will be published this month.