There are books that explain things, and then there are books that make you feel them. Cleavage by Jennifer Finney Boylan is the latter.

Told through a collection of personal essays, Boylan explores gender, identity, love, parenting, and the often unspoken space that exists between people—between who we are and how we’re seen, between expectation and reality. Her writing is sharp and honest, sometimes funny, sometimes aching, and always deeply human.

What makes this collection so impactful is how it balances the deeply personal with the universally relatable. Whether she’s talking about life before and after her gender transition, her role as a spouse and parent, or the awkward, beautiful mess of being human, every essay carries weight.

This isn’t just a book about gender. It’s about connection. About navigating change, holding onto joy, and making peace with all the contradictions we carry.

Thanks to Netgalley and the publishers for sending a digital ARC in exchange for an honest review.

I enjoy the occasional autobiographical read, and I came to Cleavage after Mad Honey - you know when you want to read more by an author and find out a bit more about them as a person?

I wasn’t sure what to expect… Cleavage takes the form of lifestyle essays on different subjects and different times from Jennifer’s life. It’s entertaining, with some style and humor. My favourite memoirs suck you in so you feel like you’ve been chatting with with the subject and really got to know them, I didn’t quite get that feeling from this book but I’m very glad I read it.

Thanks to Netgalley and Celadon Books

Full disclosure, I am wildly guilty of choosing books by their covers (and titles) while completely skipping the book blurb… and I absolutely found myself surprised by this one. The cover and title do not really match the content.

That aside, I did enjoy this memoir by trans author Jennifer Finney Boylan. Other than co-authoring Mad Honey with Jodi Picoult, I was not aware of her previous works or activism, and this book provided an interesting view into the reflections of Jennifer’s life. She gives the reader insight into her experiences, her youth, and the relationships with important people in her life - her friends, her wife, and her children. My chief compliant was the stories in this book are not linear and bounce around quite a bit, making it challenging to follow a timeline and tie events together. All in all, I enjoyed this memoir and found it enlightening.

Thank you to NetGalley and Celadon Books for the ARC in exchange for an honest review.

This one was maybe closer to 3.5 stars and might have been even more but based on the title and description I wanted something that had more of a sociology/commentary with some memoir mixed in and it turned out to be almost entirely memoir with a little bit of sociology added in here and there. If I had known this going in I likely would have liked it more but it wasn't what I was looking for right now.

"Cleavage" is a powerful memoir that explores Jennifer Boylan's distinct experiences with gender. This book delves into the triumphs and challenges of living across two genders. Boylan examines both the divisions and the commonalities between men and women. "Cleavage" offers hope for a future where everyone has the freedom to express their true selves. I was unfamiliar with Boylan before reading this book, and I enjoyed learning about her life. Being yourself can be the riskiest and bravest thing you ever do.

I found this book so interesting and eye opening. It was my first read by this author and I had a great time, I’ll definitely check her out in the future. I love a book that makes me think of different topics and this one definitely did.

I almost decided to tell Net Galley that I would not be reading this book because I thought it was a treatise on the difference between men and women and, in particular, about women as objects. I was just not in the right mood for that type of book. This was based on the title and the iconic cover picture. I’m so glad that I read the blurb and realized it was a memoir. I was initially interested because I read Mad Honey by this author and Jodi Picoult. If you want to learn more about people who are transgender, this is the book for you. It is an insightful, well written memoir from the point of view of someone who transitioned years ago. She tells her story from always knowing she was a girl to actual transition and way beyond. Very timely read, particularly in today’s environment!

I flipped the cover without any expectations about this book (or I might have had one due to the cover photo: it's a damn good photo!). I did not know about the Jennifer Finney Boylan's life and transition and its impact on bringing the experience to the front and center for the people who had to feel hidden, and it's my ignorance.

"The first half of my life was defined by a sense of yearning: I wanted to be loved, and I wanted to be my actual self. I had always assumed that if the latter came true, the first would never happen. So instead, I hoped that if the first came true, that the lack of the second would not hurt so much. I've written about this before— the way many of us hope that we might be "cured by love."" There was so much to unpack in here; I guess these few sentences summarizes her dilemma for me very well (and I don't mean dilemma about how she feels but how us humans perceive things)

I liked how Boylan still had that sunny disposition about her experience even when the US today is not the best place to have that. She kept her family and her truth as her north star and protected her identity. It was her gender that changed not her personality and things she stood up for. This was a good read to hear about the transition.

I enjoyed this memoir about Professor Jennifer Finney Boylan’s journey living as a male from childhood to middle age, including marriage and having children, and then transitioning and living the last 25 years of her life as a woman. I appreciate her sharing her story with such honesty and compassion.

This was a challenging read because rather than a cohesive narrative, each chapter is a personal essay that jumps around in time and space, weaving different stories together. Each chapter seems intended to make a different point about gender, but I sometimes struggled to figure out exactly what point she was trying to make.

I recommend this book for anyone who enjoys literary memoirs and stories of self-discovery, as well as those curious about the transgender experience.

I received a complimentary ARC through NetGalley. I volunteered to provide an honest review.

Cleavage: Men, Women and the space between us is a memoir by Jennifer Finney Boylan. It’s my first book read by her although I have others on my to be read list. The story goes through her life growing up not feeling quite like fitting, later finding her courage to transition and life after but the story jumps around a bit on what is relevant or relatability in the story. This book is really a love story, loving others of course but mostly finding love for yourself. Finding freedom for yourself. While there are serious parts, and sadness the book is packed with humor too. Sometimes I did get confused by all the names of different people and keeping it straight. I think you can get a lot out of the story even still. Definitely would recommend!

First things first — Yes, this cover and title make you think this is going to be a social sciences kind of book. It's not. It's a memoir in essays — which is also fine, but I do wonder how everyone involved in this came to the decision to package it this way. The jacket copy makes the contents somewhat more clear, at least.

I was not previous familiar with Boylan, though apparently she's been out there doing her thing for years, under her current name and as the previous version of herself. She uses her deadname a lot in some of these essays, so trans people may feel a certain way about that. I am not trans, so I cannot speak to how trans people might like this book in general, but I will say this — She's a trans elder who came out later in life, and even if her journey and way of speaking about it is not necessarily the language younger people use today, it's still important to document the experiences of trans people at ALL stages of life.

Another interesting thing is the reveal that Boylan's adult daughter is also trans, and her daughter struggled a bit with having a memoirist parent during childhood. She says that she felt a certain pressure to conform to Boylan's narrative of "Look how happy and NORMAL we are," even if that's not what her parents intended. It's a touching moment, the two of them speaking as trans adults with different perspectives. And one can see that, yes, Boylan struggles throughout her essays, even still, to not feel shame for who she is. I imagine it's a hard feeling to shake once it takes root, even knowing that it's irrational.

Boylan's examinations of being on "both sides" of the gender spectrum aren't quite as fleshed out as the subtitle of the book suggests. She mainly thinks about the trans experience in terms of being a woman —which is fine, that's who she is— but if you were hoping for more insight on the varied ways one can know and express their gender, this isn't the book. Still, it's an interesting collection of essays, and I would guess that previous fans of her work will find something of value here.

(3.5)

I love the title and the cover. The author is entertaining and I enjoyed the book but it was kind of forgettable. I did appreciate that Jennifer has experienced a lot of joy in her life which could be uplifting for a trans reader. I would say this is a fine book and wouldn’t discourage anyone from reading it but I don’t believe it’s a must read. 3.5 stars.

This book offers a straightforward look at personal identity, loss, and change. Boylan writes in a clear, heartfelt manner that drew me into her journey of coping with family loss, managing society’s expectations, and discovering her own voice. I especially liked how it was written from the viewpoint of having lived her life for a while and looking back.

What I Liked:
- The honest memories in the “Fathers” section that mix sadness with determination. Realization that not all her childhood was sad, there were plenty of fun and happy memories.
- The relatable discussion on food and body image, using everyday experiences like eating and swimming to reveal the pressures of conforming for women vs. men.
- The personal portrayal of finding an authentic voice and the challenges of adapting communication after transition.
- Boldly confronts negative societal viewpoints on transgender individuals by refuting common misconceptions and exposing the truths behind outdated stereotypes.
- The genuine depiction of relationships, where friendships and love both support and challenged her journey.

What Didn’t Quite Connect:
- The shifts between personal reflections and wider social commentary occasionally made the narrative seem uneven.
- A few memories, while rich in emotion, sometimes felt like either a tenous example of the point she was making or that they were included just to share some of her favorite memories.

Overall, Cleavage is a deeply moving memoir that challenges conventional narratives on gender and self-worth. I found that its honest insights and personal storytelling helped me reflect on what it truly means to belong.

I would like to thank NetGalley and Celadon Books for an eARC in exchange for my honest review

Thank you to Netgalley and the Publishing Company for this Advanced Readers Copy of Cleavage by Jennifer Finney Boylan!

Jennifer Finney Boylan is a gifted storyteller. Her book CLEAVAGE is a gift to us all, especially because it moves so far beyond "the trans narrative" of before I was/ now I am that is expected of memoirs by transgender writers. With Cleavage, Jennifer Finney Boylan takes us far beyond the expected and into what we can discover when we approach our lives with generosity and love. The way she discusses gender and how she was perceived at different times and how she looks back on that now is extremely moving and, at many times, hilarious. She also demonstrates such grace and acceptance of her past struggles; it's very inspiring. It also gives the author plenty of opportunities to show off her considerable skills at weaving multiple storylines/events/reflections into one chapter (or, really, essay) without losing any of the strands or confusing her readers. I plan to use the first chapter with the fireworks in one of up creative writing classes, perhaps in a pairing with one of Lidia Yuknavitch's braided essays. I also highly recommend it as a great memoir, period.

Jenny Finney Boylen, a self-proclaimed bookish, goofy (outwardly male) college professor, knew from an early age that she was a girl inside — a transgender path she did not follow until she reached her forties. Exactly how that journey unfolded, the changes encountered and the spaces left unfilled cannot help but make for fascinating reading.

Glimpses of this arise as the author describes catching up decades post-transition at her high school reunion.

“It was weird to be back in the big room after all these years with a martini and a vagina.”

Funny in places, heart-tugging in others, the author does not hold back, sharing her thoughts on her move to wholeness, and her leaning on what has held constant.

“The first half of my life was defined by yearnings: I wanted to be loved, and I wanted to be my actual self. I hoped that if the first came true, that the lack of the second would not hurt so much.”

Accompanied by the omnipresent love of her wife, Deedee, (both before and after transition), it’s hard for the reader not to feel slightly awed by the presence of this love at its most pure.

The author reflects on her womanhood as they raise their family of two, (Daddy becoming “Maddy”) — weight and newly experienced female body neurosis; the challenges of fitting in; voice insecurity; fear of violence; aging; shifting authority; love; and the losing/gaining of friends along the way.

“Who are we, now that we are old people, instead of young ones? Does love means something different to me — or to her — now that I am female?”

A fascinating blend of intimate memoir and remedial transgender education for those of us who need it, at the end of the day, this is an insightful, compassionate look at the foibles of personhood — and the ties that bind, rather than cleave us apart.

A great big thank you to #Netgalley, the author and the publisher for an ARC of this book. All thoughts presented are my own.

Jennifer Finney Boylan was an author known to be in name only, I had no idea what a rich life she lived. Relatable and humble, I found myself laughing out loud as well as being brokenhearted by her stories of what it means to be a woman, daughter, wife, and friend.

Okay, so I DNF’d at 41%. I really really wanted to enjoy this book but it was just so- boring, for lack of a better word. I wasn’t hooked enough to finish the book but I wish the author all the best.

Finished Reading

Pre-Read Notes:

I chose this one purely because of the photo on the cover. I had big boobs by the time I was 12, and I know the power of that withering look! I thought this would have some interesting things to say about life with breasts! *edit Too bad this book has nothing to do with the photo on the cover, or cleavage, for that matter.

Final Review

I was no good at any of it, no good at being a girl; on the other hand, I am not half bad at being a woman. —NORA EPHRON p5

Review and recommendations

I was honestly very surprised by the subjects covered in this book. I love memoirs of lbgtq+ people, but nothing about this book's title or cover suggests such a topic. And since those are the reasons I was compelled to read this one, I spent my entire read feeling unmoored. Also, I really don't like when authors name-drop. The fact Boylan was on Kaitlyn Jenner's show (as little more than a prop) doesn't place her in history, and it doesn't impress readers. Well, it doesn't impress me, at least. I think it's obnoxious. Also, I was really uncomfortable with how this author discusses weight and women's bodies. I don't think she *likes* her feminine figure. At least, it seems that way from these essays.

Besides that, this book is quite funny and clever. I recommend Cleavage to readers of memoir and lgbtq+ stories, as well as fans of coming of age and transformation stories.

Reading Notes

Favorite Essays:
1. "Fathers"
2. "Sons"
3. "Shadows"

A Few Words about the Essays:
1. "Both Sides Now" - Also the book's introduction, written by the author. It details the beginnings of her trans journey, all the way back to childhood.
2. "Fathers" - A touching piece about the author's unexpectedly tender relationship with her father.
3. "Food" - But I’d landed at the bottom of the chute in Girl-land to find myself a size 8, or perhaps a 10,... Eight what? you might ask. Or ten what? No one would tell me.... If you want a perfect example of exactly how fucked-up women are encouraged to be in this culture, may I present to you a snapshot of the idiotic and blissful expression upon my face the day I purchased that size 6 skirt. p23 So size 8 is "the bottom of Girl-land" huh? What Kind of fat-phobic, misogynistic, self-hating bullsh-t is this?
4. "Friends" - I’d worn a tight black dress for the occasion, fishnet stockings. All the way home, Lefty looked out the window at the shining Harvest Moon, humming softly to himself. Earlier, he’d had a knife sticking out of the side of his head. But he was okay now. p46
5. "Voice" - An excellent and surprising essay about...dummies?
6. "History" - n/a
7. "Lovers" - n/a
8. "The Unit" - Uhm...it's a story about the size of human penises.
9. "Sons" - A beautiful story about a girl and her dog, and so much more.
10. "Mothers" - Probably about what you'd expect.
11. "Shadows" - An essay about developing a woman's internal warning system.
12. "Rogues & Pixies" - It’s hard to think of many women who’ve been celebrated— loved, in fact—for their wicked, wicked ways. Mae West, maybe? Madonna? Catherine the Great? p158
13. "The Heisenberg Variations" An essay in twelve crots about being a trans creative.
14. "Liminality" - An essay about transition.
15. "Hearts & Brains" - An essay about how transitioning affects relationships.
16. "Daughters" - One day they are little blobs you hold against your breast. The next day they are driving away, leaving you forever. p209 Honestly, this essay was ruined for me by the repeated references to eating squid.
17. "Epilogue: Cleavage" - I agree with the author's friends who begged her not to call it this. It's such an ill-fitting title. Cleavage was only mentioned twice in the entire book. It's almost as ill-fitting as the cover. By the way, that photo on the cover and the women in it are only mentioned in passing, one time.

Rating: ⭐️⭐️.5 /5
Recommend? yes
Finished: Feb 11 '25
Format: accessible digital arc, NetGalley
Read this book if you like:
✏️ memoir
🌈 lgbtq+ stories
👩🏼‍🤝‍👩🏾 coming of age

Thank you to the author Jennifer Finney Boylan, publishers Celadon Books, and NetGalley for an advance accessible digital copy of CLEAVAGE. All views are mine..
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I really enjoyed how the author parsed their stories together to tell not just her experience being trans. It was an interesting opportunity to witness parts of her life and see the connections she drew. I think she allowed readers to see more of her story and how she was impacted by others in her life.

Thank you NetGalley for the opportunity to read the ARC.