In her latest memoir, “Cleavage: Men, Women, and the Space Between Us,” Jennifer Finney Boylan offers readers a poignant exploration of gender through her unique perspective as someone who has lived life as both a man and a woman. The title itself serves as a clever metaphor—reflecting both division and connection—mirroring Boylan’s own journey across the gender spectrum. Two decades after her groundbreaking bestseller “She’s Not There,” Boylan returns with a collection of essays that are by turns hilarious, heartbreaking, and profoundly insightful.
The Power of Dual Perspective
What distinguishes Boylan’s voice in the crowded field of gender studies is her firsthand experience living on both sides of the gender divide. This dual perspective allows her to observe nuances that might escape others:
“Of all the differences between manhood and womanhood I’ve experienced, there is nothing more profound than the way men keep their emotions bottled up, and women let them loose,” she writes, though she’s careful to avoid overgeneralizing or stereotyping.
Boylan’s observations are delivered with the precision of someone who has studied both worlds from the inside. She notes how differently she was treated as a professor after her transition—how students who once dutifully wrote down her words without question began challenging her authority. The same lectures delivered by Professor James Boylan were received differently when presented by Professor Jennifer Boylan.
Structure and Style: Essays as Life Fragments
The book is organized into three parts containing multiple essays examining different facets of gender experience—from food to family, voice to history. This structure works effectively, allowing Boylan to explore discrete aspects of her life while building toward a cohesive whole.
Boylan’s prose sings with a distinctive voice that balances wit and wisdom. Her humor serves as both shield and revelatory tool, often disarming readers before delivering profound insights:
“I don’t know, maybe I should have been more forgiving. After all, I didn’t have a theory for her, either,” she writes about a colleague who refused to speak to her because, as a Freudian, she “didn’t have a theory” for transgender people.
This combination of humor and poignancy creates an intimacy that pulls readers into her experience, making abstract concepts of gender identity deeply personal and relatable.
Family as Touchstone
The most affecting sections of “Cleavage” by Jennifer Finney Boylan revolve around family. Boylan’s relationships with her parents—particularly her mother, Hildegarde—provide emotional anchors throughout the narrative. When Boylan came out to her evangelical Christian mother, Hildegarde responded by taking her in her arms and saying, “Love will prevail”—a statement that becomes something of a thesis for the entire book.
Even more powerful are Boylan’s explorations of parenthood. In “Sons,” she describes her fears about how her transition might affect her children, only to have her transgender daughter, Zai, emerge years later. This creates a complex emotional landscape that Boylan navigates with extraordinary compassion:
“If accepting Zai had been that hard for me, even given all that I know, what must parents who know nothing about these issues go through? How rare, I now understand, was someone like my own evangelical Christian mom, who at the moment of crisis quoted First Corinthians, and told me love would prevail.”
Historical Context: Then vs. Now
One of the book’s most valuable contributions is its examination of how the landscape for transgender people has shifted over the past twenty years. Boylan contrasts the more naive but sometimes kinder reception she received in 2003 with today’s environment of organized political hostility:
“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.”
This historical perspective provides crucial context for understanding both progress and backlash in transgender acceptance, making the book relevant beyond personal memoir.
Criticisms: Where the Narrative Sometimes Falters
While “Cleavage” by Jennifer Finney Boylan is predominantly successful, some aspects feel less fully realized:
- Occasional repetition – Certain themes and anecdotes recur across essays, creating some redundancy
- Varying essay strength – Some pieces feel more polished and purposeful than others
- Transitions between pieces – The connections between essays occasionally feel tenuous
- Balance of metaphor – At times, Boylan’s fondness for extended metaphors can distract from her main points
The book might have benefited from tighter editing in places or a stronger thematic through-line to connect the disparate essays. Some readers may also wish for deeper exploration of certain topics that receive relatively brief treatment.
Literary Contributions and Comparisons
“Cleavage” builds on Jennifer Finney Boylan’s impressive body of work, including memoirs like “I’m Looking Through You” and “Stuck in the Middle with You,” and her novel “Long Black Veil.” Her recent collaboration with Jodi Picoult on “Mad Honey” (which she describes beginning with a shared dream) demonstrates her growing literary presence.
Boylan’s work stands alongside other important trans memoirs like Deirdre McCloskey’s “Crossing” and Janet Mock’s “Redefining Realness,” though her distinctive humor and literary craft set her voice apart. Her ability to blend memoir with cultural commentary recalls writers like Roxane Gay and David Sedaris, creating work that is simultaneously personal and universal.
The Heart of “Cleavage”: Identity Beyond Binaries
At its core, “Cleavage” by Jennifer Finney Boylan challenges simplistic understandings of gender identity. She writes:
“It may be that what’s in your pants is less important than what’s between your ears.”
Yet she also resists reducing transgender identity to biology:
“Trans people are not broken. And, in fact, trying to open people’s hearts by saying, Check out my brain! can do more harm than good, because this line of argument delegitimizes the experiences of many trans folks”
This nuanced approach makes “Cleavage” valuable not just for those interested in transgender experiences, but for anyone seeking to understand how identity is formed, challenged, and affirmed.
Closing Thoughts: A Bridge Between Worlds
Jennifer Finney Boylan has created something remarkable with “Cleavage”—a memoir that serves as both personal testimony and cultural critique. By sharing her experiences living on both sides of the gender divide, she provides readers with unique insights into what it means to be human beyond the constraints of gender.
The book’s title ultimately proves perfect—referring not just to division but also to connection, to the space between presumed opposites. As Boylan writes in her epilogue:
“In the end, the bodies we find ourselves in may matter less than the souls that inhabit them. And during our time on earth, it is surely no sin to do what you can to find your happiness within the body you’re in.”
“Cleavage” by Jennifer Finney Boylan is an essential addition to the literature of gender studies, family dynamics, and American identity. Despite minor imperfections, it stands as a testament to Boylan’s skill as a writer and her courage as a human being, revealing how one person’s journey across gender lines can illuminate universal truths about love, acceptance, and what it means to be truly seen.