Editor’s note: This segment was rebroadcast on Jan. 28, 2026. Click here for that audio.
Here & Now‘s Robin Young speaks with author and transgender advocate Jennifer Finney Boylan about her new book of essays “Cleavage: Men, Women, and the Space Between Us.”
Book excerpt: ‘Cleavage: Men, Women, and the Space Between Us’
By Jennifer Finney Boylan
BOTH SIDES NOW
An Introduction
I was born in 1958, on June 22nd, the second day of summer. It was also the birthday of Kris Kristofferson and Meryl Streep, both of whom I later resembled, although not at the same time.
I began the story of my life with these words in She’s Not There, a memoir published in 2003. At the time it seemed reasonable enough, beginning with the beginning.
Now I wonder whether I chose the right companions. Instead of Streep and Kristofferson, I could just as easily have picked others born that day—Elizabeth Warren, say, or John Dillinger, or Dan Brown. Would my book have landed differently if my chaperones had been the senator, or the gangster, or the author of The Da Vinci Code?
Sometimes I think about it, all the other lives I might have led.
At the time of its publication, She’s Not There was a real brouhaha. I was on Oprah five times, Larry King twice. Will Forte imitated me on Saturday Night Live. Kirkus Reviews described my writing as “sheer as stockings,” which was nice. Though hardly the first trans memoir—not by a million years—it came out at a moment when things were changing, at least a little. I hope She’s Not There—the book I call SNoT—did push the needle, at a crucial moment. The publisher’s promotional copy now calls it “the book that jump started the transgender rights movement.” Big words.
But She’s Not There was a story told by someone for whom everything was new; the voice is that of a woman who’s still in the late stages of an amazing ride, her clothes still smoking after she’s been shot out of a cannon. Memoirs of transgender people are almost always about that moment, when a little morning dew is still twinkling on the cobwebs of their transitions.
There’s a good reason why so many stories about people like me focus on that passage: it is, by any measure, an astonishing thing. What in the world is it like to go from a man to a woman, or vice versa, or to some identity even more liberating than that?
But a more important, if less scandalous, question is: What’s it like for those who finally have what they’ve been impossibly yearning for all their lives? Indeed, what’s life like for transgender people as we age, as we inevitably morph from someone covered with sequins into someone whose hair is gray? And what of the people we’ve been, and our histories from the times before? Surely all of that can’t just vanish, like breath on a mirror?
I’ve spent almost a third of my life over here. I have stories to tell, now that my spangles are no longer aflame, about the difference between the worlds of men and of women, not to mention the fertile territory that lies in between.
But let’s also admit there’s a huge chunk of the population—the majority, maybe?—that still doesn’t understand this trans business at all, people with good hearts who nonetheless could not with any certainty tell you the difference between a transgender person and the Trans-Siberian
Railroad. It doesn’t help that the best-known trans person in the country is probably Caitlyn Jenner, whom no one could claim has emerged as the transgender Encyclopedia Brown.
The stories in this book examine the differences between manhood and womanhood, as I have experienced them, in everything from food to fashion, from love to loss.
They also address the differences between coming out now, in the cur- rent environment of blowback and fear, and coming out twenty-five years ago, when transness—to some people—seemed a thing as obscure as membership in the Royal Antediluvian Order of Buffaloes.
Back then, in an era before people received formal instructions on how to hate us, many individuals encountering a transgender person for the first time were left with nothing to fall back upon, by way of guidance, than their own sense of human decency. When I came out to my evangelical Christian mother, for instance, she didn’t respond to her weeping child with a lecture about the dangers of trans women in sports; or concerned theories about “social contagions.”
Instead she took me in her arms, and wiped my tears away, and said, Love will prevail.
I have been blessed by good fortune in the passage that I have made. But I know plenty of people who were not so lucky, people who even now wait in vain for the people that they love to show them a single crumb of kindness.
Perhaps the central question of this book is not specific to gender at all. Instead, it’s the universal dilemma at the heart of so much human trouble: Why is change the thing we all long for, as well as the thing we most fear?
I was born on June 22, 1958, the second day of summer. It was also the birthday of Billy Wilder and Cyndi Lauper, both of whom I later resembled, although not at the same time.
It was Cyndi Lauper who sang, back in 1983, that girls just want to have fun. We want other things as well, of course: to be loved; to be respected; to be safe from violence and fear; to be able to make our own decisions about our own bodies. But sure, fun is on the list. Emma Gold- man, the anarchist, is credited with saying, “If I can’t dance, I don’t want to be part of your revolution,” although apparently she never actually said that. But she did say that everyone had the right to self-expression, and “beautiful, radiant things.”
I can tell you that in the Days Before as well as in the Days After I have caught fleeting glimpses of things both beautiful and radiant. I saw them in the sky above me, after the wind in Nova Scotia blew me back from the edge of a cliff I was about to leap off of. I saw them in a dark room, as my future wife unexpectedly stepped toward me from the shadows. And I saw them in my mother’s eyes as she folded my weeping self into her arms and quoted First Corinthians: These three remain: faith, hope and love. But the greatest of these is love.
Billy Wilder, for his part, directed and co-wrote Some Like It Hot, the film that ends with Jack Lemmon (as Daphne) trying to explain to Joe E. Brown (as Osgood, her swain) why they can never be married.
Daphne looks into the distance and says, wistfully, “I can never have children!”
“We’ll adopt some,” says Osgood, without any reservation.
I have a question about Osgood. Is he generous and open-minded, the kindest man alive? Or is he just, you know: absolutely demented?
After all this time, I’m still not sure, even though I’ve looked at things from both sides now. Maybe, at this late date, it doesn’t matter. It’s life’s illusions I recall. I really don’t know men, or women, at all.
“You don’t understand, Osgood!” Daphne cries. She rips off her wig. “I’m a man!”
Osgood looks at her with obliviousness—or what might, just possibly, be love. “Well,” he says. “Nobody’s perfect.”
From “Cleavage” by Jennifer Finney Boylan. Copyright 2025 by the author and reprinted with permission of Celadon Books, a division of Macmillan Publishing Group, LLC.
This article was originally published on WBUR.org.
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