Vagina Notwithstanding

How a little gender chaos improves our lives

Jenny Boylan
Galleys
14 min readSep 22, 2016

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Jennifer/James Boylan at the Museum of Retired Ventriloquists’ Dummies, 1982. (Photo by Peter Frumkin.)

“What about Hardy?” I asked my wife, holding up a ventriloquists’ dummy. “Keep, or throw out?”

Hardy was the surviving partner of a set of Laurel and Hardy dummies, although by the time we came along, Laurel had headed out on his own. We’d been bequeathed Hardy by a family friend, as a gift for our son, Zach, when he was a child. But Zach hated Hardy, hated him as if we’d tried to give him a bag of venomous snakes for a present instead. He said Hardy gave him nightmares, and I could see why. What with the schnurrbart mustache, the puppet did look a teensy little bit like Mr. Adolf Hitler. And so Zach had banished Hardy to the back of a closet.

Which was where I found him, years later, as I prepared to pack up our home for good.

“Out,” said Deedie, answering my question.

“Yeah,” I said, although I felt a little bad that Hardy was coming to the end of the line, being so redolent, even in his exile, of my son’s early childhood. Still, when you pack up a house, you can’t get sentimental over everything. It’s heartbreaking, really, to part with things that connect you to specific moments of a vanished past. Zach was twenty years old now, a junior at Vassar; we didn’t have that many of the toys and things that evoked his days as a tuba playing, roly-poly child. I put my hand up Hardy’s neck, and blinked his eyes.

The puppet took his measure of our house. The books were in boxes. A pile of clothes for Goodwill was stacked up on the floor. The convertible sofa-bed I’d slept on in grad school was being carried off to a Dumpster. There were some boxes piled up in the basement we could not bear to open; we knew we were better off not knowing. The bottom of one such box had torn open as Deedie and I carried it out to the trash, spilling the dress she had worn to her high school graduation onto the asphalt driveway. “Oh, look at it,” she said, lovingly, of the turquoise 1970s hippie gown. “Just look at it.”

Hardy spun his head around, lamenting the state of our disassembled house. “Well, Stanley,” he said. “This is another fine mess you’ve gotten us in.”

“Out,” said Deedie.

The house-moving was only part of a much larger stage of upheaval in our lives that Deedie and I had christened Project Kablooey. Weeks before, our younger son, Sean, had departed for college, leaving us empty nesters. Simultaneously, after twenty-five years as a professor at the college I loved in Maine, I’d taken on a new position as the writer in residence at Barnard, down in New York City. That had entailed finding a sublet, moving a ton of things down to Manhattan. Finally, we’d decided to go ahead with renovations at the house that had been our summer place, turning that into our primary Maine residence and selling the house that we’d raised the boys in. “If we’re going to blow up our lives,” Deedie had said, referring to Project Kablooey, “we may as well go the whole hog.”

It was not the first time our hog was whole. In 2000, after bearing the burden in secret for the first twelve years of our supposedly heterosexual marriage, I’d finally come out to Deedie as transgender. Everyone always says the truth will set you free, but the people who say that have probably never seen the effect that revealing yourself as trans has upon someone that you love. For years and years, I’d felt that the trans thing was my secret to keep, and that by keeping it I was shielding my wife and sons from harm. But just after New Years, in the year of the new millennium, I’d reached a point where I knew I had to be out with the truth. It felt, literally, like a life or death decision to me. And so I’d spilled the beans.

In the days and months that followed, sometimes it seemed like all we did was weep. For Deedie, there were times when she felt she had no good choices at all. Either she could abandon the person she loved at the moment of her — my — greatest need, or she could stay with me as I went through a process that, almost by definition, would take the person Deedie loved away from her. I’d stand there in my beat-up wig and abundant makeup and declaim, “But I’m the same person!”

Deedie just shook her head. “In what sense?” she asked.

I’d given many hours of thought to the question of what I would do if the people I loved, and Deedie, above all, had rejected me once and for all. At times I imagined starting over completely — moving to a new town, taking up a new profession. There was a little while when I thought about giving up teaching and becoming a nurse, or a social worker, or a minister. I wanted a profession in which I could help people whose hearts had been torn out, I guess. Being, as I was, something of an expert in the field.

After transition, though, I returned, for the most part, to the life I had known, in the spirit of that well-worn T.S. Eliot poem in which explorers arrive where we started and know the place for the first time. I realized that there was nothing I liked as much as teaching college students; it was what I was wired for, and there was no point in taking up a whole different profession just for the sake of a fresh start. Deedie, for her part, realized that there was generally no one whose jokes she liked as much as my own, vagina notwithstanding. And so we settled into our new life as two middle-aged women: not, to be certain, the lovers we had been, but, for better or worse, as the loving partners we had become. There were plenty of people, including the friend who had bequeathed us Hardy, who failed to believe that either Deedie or I could be happy with the compromise at the center of our lives. But there we were, more than a decade later, together packing up our old house. It was, as Hardy himself might have noted, a fine mess.

Then, against all odds, I won something called the “Amtrak Residency.” As one of Amtrak’s Writers-in-Residence, I was given the opportunity to travel around the country on a long-distance sleeper train, writing and editing and — most important of all — looking out the window going Duh. About half of my friends wrinkled their noses at this prospect, asking, “Who on earth would want to ride around on a train for two weeks?” The others sighed wistfully and said, “Oh. I’ve always wanted to do that.” I think the ones who most lusted after the experience were the same ones who, like me, were virtuosos of the fine art of looking out the window going Duh.

One day, I rushed into a room where Deedie was rolling china plates into newspaper, and triumphantly announced: “I’ve discovered the exact notes of a train whistle, at last! It’s D sharp, F sharp, G sharp, B and D sharp.”

She nodded lovingly, in the same way you might nod at, say, your son when he announces to you that he’s discovered a secret anti-gravity gun! “It’s a B major sixth,” I added.

“I can see you’re very happy at having found that out,” she said.

“It is pretty cool,” I said. I looked at the box she was packing. “Is there anything I can do to help?”

“Yes,” she said. “You can make me a martini.”

On Halloween, the night before the residency began, I spent the night playing rock and roll music in a barn with some friends. I played two songs that night, one of which was “Ghost Riders in the Sky,” and one of which was not. The next morning I got up at 3:15 AM, kissed Deedie on the cheek, and slipped out the door with my suitcase. Ranger, the dog, raised an ear. “What are you doing?” he wanted to know.

It was hard to explain.

A few hours later, I was riding the Downeaster from Freeport, Maine, to Boston. From there I stepped onto the Lake Shore Limited and headed out to Chicago, and from there onto the California Zephyr to San Francisco. America rushed by my window, in all its cussed, contradictory charm.

Jennifer & Deirdre Boylan, 2015. “Yes, she said. “You can make me a martini.”

We crossed the Sierras via the Donner Pass. Far below us was Donner Lake, where that doomed group of early settlers had become trapped one winter and their nightmare began. I looked out at the horizon, eating ice cream. I was reading James Stephen’s The Crock of Gold, a scene in which the god Pan seduces the shepherd girl: “Come away with me, Shepherd Girl, through the fields, and we will be careless and happy, and we will leave thought to find us when it can, for that is the duty of thought, and it is more anxious to discover us than we are to be found. So Caitilin Ni Murrachu arose and went with him through the fields, and she did not go with him because of love, nor because his words had been understood by her, but only because he was naked and unashamed.”

I had supper with many strangers during that cross-country trip — an Amish couple who did not approve of music; a man who owned his own storage unit business; a young psychotherapist who was reading a biography of William James — but none of them resembled the great god Pan exactly, what with the cloven hooves. Still, I was not entirely immune to the melody of his pipes. In San Francisco I was met at the station by my friend Noelle, who plunked me down in the lobby of a hotel called the Rex and ordered something called a Moscow Mule. When we finished the first round, she ordered another.

“So what’s the deal with your marriage?” she asked me.

“The deal, what do you mean the deal?”

“I mean, when you start teaching at Barnard and Deedie is back in Maine, are you going to have an open relationship?”

“I don’t think so,” I said.

“Well, that’s good,” she said. Noelle was in the midst of a big divorce. “Whenever people say they’re going to have an open relationship, what really happens is, one person has an affair and the other person gets hurt.”

“Yeah. I don’t think that’s in the cards for me.”

“Still you want to keep your options open,” said Noelle. “I want for you what happened to me. One day, my friend Mark kissed me, and just like that, my vagina went whoa.”

I laughed. “That’s sweet, that you want that for me,” I said. “But I don’t see that happening.”

“But Jenny — don’t you want more, sometimes? More than what you’ve got?”

“Well,” I said. “No one ever wants less.”

A few days later, I took the Coast Starlight up to Seattle, then slipped onto the Empire Builder headed east through Idaho, and Montana. In North Dakota, we passed through the “man-camps” of the Bakken oil shale. There was a vast collection of mobile homes. Someone told me 1200 men lived there. A guy standing by the side of the roadbed raised his hand as the Empire Builder passed by, and waved.

Later, Deedie called me on the phone, and gave me an update on Project Kablooey. The sheetrock was up in the new kitchen. The chimney was done. “I love you,” she said.

“I love you, too,” I said.

The supervisor of my sleeping car, Dennis, poked his head in the door a little later. He was a lovely Irishman who had the gift of gab, to put it mildly. Earlier, he had described the experience of being on a long-distance train this way: “Each trip is a micro sociological experiment in its own right in that a host of disparate elements are tossed together in one sense against their will.”

Now he wanted to make sure I was paying attention to the sunset. “Don’t forget to look at everything.”

I looked, and he was right. It was a world of wonders out there.

“It’s phantasmagorical,” Dennis said. His eyes twinkled, and I thought, you know, Jennifer Boylan, that person there is not an unhandsome man.

I went back to The Crock of Gold. Now Caitlin Ni Murrachu was leaving Pan, and beginning a new relationship with Angus Og. “And she went with him not because she had understood his words, nor because he was naked and unashamed, but only because his need of her was very great, and, therefore, she loved him, and stayed his feet in the way, and was concerned lest he should stumble.”

Thirty years earlier, long before transition, I’d stopped off at something called Lee Brewster’s Mardi Gras Boutique, in New York, where I lived back then. It was like a mini-department store for trans women. As I was purchasing a long blonde wig, a businessman came up to me and said, “I love cross dressing. Do you love cross dressing?”

“Could be,” I said. I didn’t think of it as cross-dressing per se. I thought of as the truth.

I’d lived on 108th Street and Amsterdam then, one floor above what might be politely referred to as an S&M Dungeon. Barnard College, and Columbia University, loomed a few blocks north of my apartment, but I had almost no interaction with its world, which felt walled off and inaccessible. I remember one time trying in vain to gain access to the Columbia library, which the psychiatrist I was seeing had encouraged me to visit in order to learn more about transsexuality. But a guard at the entrance told me I couldn’t go in, since of course I was not a Columbia student.

It was a cold, gray day, and I stood for a moment letting his words sink in. That library felt like a symbol of everything to me back then as a young, yearning artist — that there was a whole world waiting for me somewhere, if only I could learn to elude its gatekeepers.

So instead, in a vague attempt at cheering myself up, I headed toward the dark caverns of the Cathedral of St. John the Devine, ducking in the huge doorway just as it began to snow outside. John Lennon had been killed the week before, less than a month after Reagan had been elected, and there was a biting melancholy in my heart, as if it was not clear whether the universe I lived in was the one in which I wanted to dwell. I sat there in a lachrymose trance. And then, unexpectedly, an organist at the cathedral began practicing for the following day’s service. There, in that beautiful space, I heard the melody, performed in a set of variations for pipe organ, of John Lennon’s “Imagine.”

When the piece was over, I walked back out onto Amsterdam, my heart strangely lighter, open again. The city, in the interim, had been transformed by the snow into something crystalline and unrecognizable — a place out of Dickens, or maybe Tolkien. I felt, as I stood there on the steps of the cathedral, that things I had thought were impossible could in fact become real — that I would learn, in time, how to tell my story; that I would find the courage to come out as trans and begin to live an authentic life.

After the Amtrak gig, I headed down to New York to get my office and our apartment set up. I was back on the Upper West Side, only two blocks from the place I’d rented in 1980. But now, three decades later, I was a middle-aged woman named Jennifer, not a young man named Jim, and I was set to begin an appointment as an endowed chair at Barnard, named after a woman who once wrote, “It turned out that when my younger self thought of taking wing, she wanted only to let her spirit soar.”

The S&M dungeon was gone, transformed into a ritzy apartment building with a doorman. I passed it one day en route to campus, where I was headed to do some research. When I arrived at the Columbia Library, I showed the guard my ID. “Hello Professor,” he said, and he held open the gate open so that I could walk in.

I had been hoping that Project Kablooey would be complete by the time I headed to New York, but what with one thing and another, the construction on the new place was delayed. The mason had built the chimney, though. And Deedie and I had spent an entire afternoon at a home supply store, picking out toilets. It was surprising, how many choices there were.

The Boylan family, 2016. “I told you,” he said. “It is phantasmagorical.”

I can’t say I’m any better at upheaval than I ever was, although after all these years, I guess the process has become a little more familiar. A dozen years ago, Deedie and I went through a kind of turmoil that few couples have to endure, and somehow we fought our way back to a place of stability and peace. Now here we are, with lots of the pieces of our lives still up in the air. It’s unsettling, but I also wonder if true happiness requires more than a little kablooey now and again. It is good to come into the station, to be sure. But it’s also necessary, now and again, to set out for points unknown.

One morning, on the California Zephyr — just weeks before my new teaching gig — I sat up in my sleeping chamber and looked outside. The clock read 4:30, and the world was dark. The train rocked from side to side, and the engineer blew the whistle. B major sixth.

I put on my terry cloth robe and left my “roomette,” a chamber which one of my companions in the dining car, a Texan, had described as “so small you couldn’t cuss out a cat there without getting fur in your mouth.” I slipped down to the observation car with my computer and a cup of coffee. I sat there and wrote for an hour or two as the skies turned pink above the Rockies.

I thought about Deedie and my boys, about the long road we had travelled, about the long road that lay ahead, about the strange blessings of turbulence.

The dawn came up like thunder. A woman sitting next to me started to sing, “Here Comes the Sun.” Little darling, it’s been a long cold lonely winter. For a few seconds, everyone in the observation car — a bunch of complete strangers — sang it all together.

I headed back to my roomette and watched the day break on the land.

Then there was a knock on the door. It was Dennis. He raised an eyebrow. Dennis wasn’t exactly naked and unashamed at that moment, but it wasn’t impossible to imagine that he’d come to stay my feet in the way.

Lest I should stumble.

I imagined an alternative universe, one in which Dennis offered me the chance to learn what it might be like if my friend Zoe’s dream for me came true, and my vagina went whoa.

I did want my spirits to soar, to let my heart take wing. But it also occurred to me that even in the realm of Kablooey, there are limits. Aren’t there?

Dennis smiled at the view through my roomette window. Yellow light was shining on the Rockies. “I told you,” he said. It is phantasmagorical.”

It was hard to deny. The man had a point.

“Out?” I said.

This essay is excerpted from The Bitch is Back: Older, Wiser, and (Getting) Happier, edited by Cathi Hanauer, to be published 9/27 by William Morrow, an imprint of HarperCollins.

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Jenny Boylan
Galleys

Anna Quindlen Writer in Residence at Barnard College of Columbia University; New York Times Contributing Opinion Writer; National Co-chair, GLAAD.