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Stuck in the Middle With You: A Memoir of Parenting in Three Genders

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New York Times bestseller and acclaimed author Jennifer Finney Boylan returns with a remarkable memoir about gender and parenting, including incredible interviews discussing gender, how families are shaped, and the difficulties and wonders of being human.

A father for ten years, a mother for eight, and for a time in between, neither, or both ("the parental version of the schnoodle, or the cockapoo"), Jennifer Finney Boylan has seen parenthood from both sides of the gender divide. When her two children were young, Boylan came out as transgender, and as Jenny transitioned from a man to a woman and from a father to a mother, her family faced unique challenges and questions. In this thoughtful, tear-jerking, hilarious memoir, Jenny asks what it means to be a father, or a mother, and to what extent gender shades our experiences as parents. "It is my hope," she writes, "that having a father who became a woman in turn helped my sons become better men."

Through both her own story and incredibly insightful interviews with others, including Richard Russo, Edward Albee, Ann Beattie, Augusten Burroughs, Susan Minot, Trey Ellis, Timothy Kreider, and more, Jenny examines relationships with fathers and mothers, people's memories of the children they were and the parents they became, and the many different ways a family can be. Followed by an Afterword by Anna Quindlen that includes Jenny and her wife discussing the challenges they've faced and the love they share, Stuck in the Middle with You is a brilliant meditation on raising – and on being – a child.

304 pages, Hardcover

First published April 28, 2013

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About the author

Jennifer Finney Boylan

31 books1,528 followers
Jennifer Finney Boylan is a widely praised author and professor.

Edward Albee summed up her oeuvre in 1988: -- "Boylan observes carefully, and with love. [Her] levitating wit is wisely tethered to a humane concern…. I often broke into laughter, and was now and again, struck with wonder."

Jenny's memoir, She's Not There, published by Broadway Books in 2003, was one of the first bestselling works by a transgendered American; until 2001 she published under the name James Boylan. She's Not There, currently in its eighth printing, is popular both as a textbook in high schools and colleges as well as with readers's groups. The paperback edition contains a "readers guide" in addition to the main text, which consists not only of Jenny's insights on "a life in two genders" but also includes an afterword by Pultizer Prize winner Richard Russo, whose friendship with James, and later with Jennifer, provides part of the books narrative.

She's Not There won an award from the Lambda LIterary Foundation in 2004, the year after its initial publication. The book has since been published in many foreign editions, and was an alternate selection of the Book-of-the-Month Club. Anna Quindlen called it “a very funny memoir of growing up confused, and a very smart consideration of what it means to be a woman.”

Her 2008 memoir, I'm Looking Through You, is about growing up in a haunted house. While trans issues form part of the exposition of the book, the primary focus of I'm Looking Through You is on what it means to be "haunted," and how we all seek to find peace with our various ghosts, both the supernatural and the all-too-human.

Jenny has been a frequent guest on a number of national television and radio programs, including three visits to the Oprah Winfrey Show. She has also appeared on the Larry King Show, The Today Show and been the subject of a documentary on CBS News’ 48 Hours. She has also appeared on a wide range of local and syndicated television shows, as well as NPR's Marketplace and the Diane Rehm show. In 2007 she played herself on two episodes of ABC's "All My Children." She has spoken widely around the country on gender and imagination, at venues including the National Press Club in Washington, D.C. and the New Jersey State Theatre. She has given plenary and keynote speeches at conferences on diversity and scholarship around the country, and at colleges and universities including Amherst, Wesleyan, Dartmouth, Columbia, Vanderbilt, Duke, Bucknell, Dickinson, Bates, Ohio State, Middlebury, Gettysburg, Georgia State, the University of Puget Sound, and Westminster College in Salt Lake City. She has spoken at law firms, at corporate events, and at bookstores from Seattle to Vermont.

Her nonfiction has appeared on the op/ed pages of the New York Times, in GQ magazine, Allure, and Glamour. She is also an ongoing contributor to Conde Nast Traveler magazine; her most recent work there was on Easter Island, published in the January 2007 issue.

Boylan's first book, a collection of stories entitled Remind Me To Murder You Later, was published by Johns Hopkins University Press in 1988. Her first novel, The Planets, was published in 1991 by Poseidon Press. (Simon and Schuster). Loosely based upon the classical piece of music by Gustav Holst, The Planets followed the lives of several fictional characters in the real town of Centralia, Pennsylvania, which has been afflicted by an underground coal fire since the early 1960s.

Her second novel, The Constellations follows the lives of several of the characters from The Planets, some of whom flee from angry cows, discover a latex brain, and begin a life of dognapping.

Her 1997 novel, Getting In, published by Warner Books, focused on four high school students who go on quests to get into college. The novel was optioned for film by Renny Harlin and Geena Davis, and Jenny was tapped to write the initial screenplay for New Line Cinema.

Born in 1958 in Valley Forge, Boylan

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Displaying 1 - 30 of 181 reviews
Profile Image for Kaethe.
6,545 reviews531 followers
August 6, 2020
Finney Boylan is now my favorite memoir writer. Dogs and ghosts await me, and that is very happy -making news.

Library copy
Profile Image for Bonnie G..
1,755 reviews411 followers
May 8, 2020
In return for my honest review I received this book free from Librarything Early Reviewers. This did not affect my review.

So...this was disappointing. I loved Boylan's first memoir,She's Not There: A Life in Two Genders This book started out with promise, but I had a number of issues with it in the end.

Boylan actually writes very little about parenting or family. Her kids are exquisitely well adjusted and high achieving. Neither she nor her wife are particularly troubled by the fact that they haven't had sex since the transition and will never have sex again because who needs sex when there is love? Yeah, right.

Boylan tells a few VERY select stories, and augments this very skimpy memoir with interviews with well known literary folks. These interviews are ostensibly (sometimes actually) centered on parenting and on being parented. Other than learning that Edward Albee, a playwright whose work I have loved, was an asshat, these interviews taught me nothing. The interviews did not broaden or inform my view of parenting. They were, frankly, really bad. Boylan has done some reporting, so I would have expected her to be a better interviewer. I think when friends interview friends it doesn't work. Anyone who has read Interview Magazine knows this. Whatever the reason, these interviews are awful.

Focusing on the fact the interviews were not done well raises the question of whether the interviews belong in this book. I say they do not. This book holds itself out as a memoir of parenting as a trans woman, and it is not. The only material which really covers this are a few stories about how Jenny is worried that her transition will create issues. Of course it is all in her head and her children are really truly 100% unaffected by her decision to transition. That may be how she chooses to see it, but kids are judged by their peers all the time. That judgment includes peers' views of parents. I am not saying in any way that her kids are going to be screwed up by her transition, I am not even saying they might not grow to be better men because of it, I am just saying she is claiming that the transition did not affect her sons in any way, and I am not buying what she is selling. A more honest discussion would have been both more interesting and more educational and empowering for parents raising their children in non-traditional environments.

In the end this book came off as lazy and dishonest, and that is a shame. Boylan is a great writer and she has life experience which could have been turned into a really good book. Oh well, 2 kids in elite colleges costs. I wish the family well, they seem like nice people.
Profile Image for Ellen.
1,578 reviews449 followers
February 10, 2013
Stuck in the Middle with You: A Memoir of Parenting in Three Genders is the memoir of Jennifer Finney Boylan that reflects upon her role as parent and how it did-or did not- change as the result of her transition from male to female. Boylan has written elsewhere of her transgender issues and her focus here is primarily on to what degree-if any-it has impacted upon her parenting. Boylan has remained married to her pre-transition spouse and the book touches lightly upon the experience this has been for the wife-Deedee-in this relationship. On the whole, Boylan concludes, her gender change does not seem to have had a negative impact on her sons.

The narrative, an able accounting of the experience of parenting for anyone, is interspersed with interviews from friends of Boylan, writers such as Edward Albee, Richard Russo, and Ann Beattie, as well as the experience of a former nanny of Boylan's. The interviewees reflect on their experience of either being parented or being parents and on their decisions to have or not have children of their own.

Stuck in the Middle with You: A Memoir of Parenting in Three Genders is an engaging if not compelling book that hangs somewhat loosely on the thread of Boylan's transgender experience and even more loosely on the general experience of family. I would have wished for a more coherent reflection on any one of these issues but as it is, I enjoyed the book and found myself feeling as though I knew Boylan and her family personally. What comes across clearly, to me, is that the experience of parenting has more to do with love and caring than it does with gender.
Profile Image for Asho.
1,846 reviews12 followers
June 23, 2013
First, let me say that I enjoyed Boylan's writing style. The memoir chapters in this book left me hungry for more of her stories and experiences. I also enjoyed the interviews and was impressed by the caliber of featured interview subjects (also: wow, some people have horrendous parents).
I was disappointed, though, that this book seemed to only skim the surface of questions of gender and parenting roles. I wish Boylan had done more exploration of traditional gender roles. In trying to make the point that there aren't big differences generally speaking, and certainly not harmful ones, in what mothers do and fathers do, she ended up not actually talking much about parenting. I am not sure I am making much sense here...I suppose I just wanted more of the nitty-gritty. This was more about the emotions of parenting than the practicalities of parenting, and I wish I had heard more about the whole picture. For instance, I have no idea from reading this if Boylan felt the pressure many female academics feel as they try to balance work and family, pressure that--in my experience, at least--seems largely absent for males. Not that men don't want to be with their families and raise their children, just that society still doesn't expect them to take on that role in as all-encompassing a way as we expect it of females. I would have loved to hear more about how transitioning affected the work/life balance and her perception of traditional male roles of family breadwinner, head of household, etc. Basically, where was the explanation of the traditional gender roles? I suppose Boylan's basic point was, "Those roles shouldn't matter because in the end parents are parents, no matter the sex/gender." And yet its idealistic to say that they don't matter. They do, because they still exist to some degree, and I wish she had grappled with them a bit more because she's in a unique position of having experienced parenthood and academia as both a father and a mother.
Also, Boylan makes the point in the post-book interview that it is her story to tell, not her wife's. Fair enough. However, I think when talking about parenting, the best judge of how a parent has ultimately done at his/her task is the testimony of his/her children. It doesn't matter how I perceive my role as a mother, or how great a parent others think I am, if my own son disagrees. So in this case I think perhaps this memoir was a bit premature. I wish Boylan had waited to write it until her sons were older and more established in their own lives and careers (if I gather correctly, they are late high school age, maybe early college age at oldest). I'd love to know what they would say about their upbringing. I doubt it would contradict Boylan's story, but I'd still like the nuanced view I think her kids could bring to the table.
Overall, this book didn't quite hit the spot 100%, but it did leave me wanting to explore more of Boylan's writing, particularly her earlier memoir.
Profile Image for Melissa T.
612 reviews30 followers
June 23, 2019
This was an interesting look at gender identity, and how that changed for Jennifer Finney Boylan as she transitioned from male to female.

She looked at it from an interesting perspective. Am I still the same parent I was when I used to be their father?

Of course not everything was the same. Her wife had to adjust to losing a husband, her sons to losing a father. But, they gained, as they put it a"Maddy" (half mommy, half daddy) and I think that had a profoundly positive effect on them. Boylan's sons are sensitive, caring, well rounded individuals. And so wise. Some of the things they said as little boys just got me right in the heart!

Boylan portrays both sides of the issue, even within her own life. She had family who was supportive, and family who was not. She had situations where she was comfortable inher womanhood, and situations where she wasn't.

Overall I enjoyed looking at this, as well as the other perspectives she covered on parenthood, with the essays from others she included.

Though if I'm honest, they were actually my least favorite part of the book. I felt that her story of her family was enough to hold up the book. The essays felt like a distraction to me.

Profile Image for Leslie.
995 reviews30 followers
June 18, 2014
I won this book from a goodreads, first reads giveaway. It has in no way, influenced my opinion.
In college, I had a class where a transgendered (male to female) came in and told her story. I remember that my friend and I were quite fascinated. You hear about it but to see it right in front of your face, really opens your eyes. It was one of the experiences from college that really stayed with me. They are just regular people. So I was interested in what this book would be about. It fell really flat for me.

One of my "pet peeves" about reading, is when I'm being told a story but in the middle of that story, another story starts. Before that second story finishes, I have completely forgotten what the initial story is. I then have to try hard to remember what the beginning was when we get back into the original story. Sound confusing? It is. It's annoying! I don't like when authors do this over and over. This happens a lot in this book. It was just really dry and it honestly took me a long time to get through this book.

The most interesting part of this book is really all the interviews with all of her friends. Their life story about their parents and some of the things they have gone through to be parents themselves. To me that was the core of this book. The rest of the stories about Jenny felt more like just fluff to fill pages. It was also a bit annoying to have the interview at the end with Deedie and Jenny and just focus on the first book. I didn't read the first book, so I had no idea what they were talking about. That interview should have been at the back of the first book, not this one.

Overall, this book was just okay.
Profile Image for Kate.
Author 7 books255 followers
July 10, 2014
This book is like a quilt woven from many different pieces. I was surprised to find especially pleasurable the interludes of interviews with various literary figures, and other people in Jenny's life. It felt like I was sitting in the room with them as they talked about family, gender, literature, life...

And then there's the other (related) focus of the book, Jenny's relationship with her kids and spouse before and after her gender reassignment. These parts are written with such tenderness, vulnerability and humor--hallmarks of Jenny's other book I read, "She's Not There."

Another pleasure of this book for me, as a writer, is the fun way she weaves literary references into the book--and how I got to "sit in" on conversations between her and other writers (such as Agustin Burroughs, Edward Albee, and Anne Beattie).

There are a lot of moving parts to this book, and I enjoyed the way the various aspects themes emerged. It reminded me there are as many ways to write a book as there are writers--and as many ways to live as there are people.
Profile Image for Rebecca.
193 reviews
June 6, 2013
a just ok memoir about a father who changed to a mother. Sounds like a topic that one would remember reading about, but I suspect that I'll forget this book very soon
892 reviews1 follower
March 28, 2024
The topic of gender identity is, to say the least, extremely complex. Anyone who is familiar with the work of Oliver Sacks knows that there are many different ways in which our internal perceptions of ourselves. do not match our external reality. In addition, it is difficult to pin down the truth about what it means to be male, female, androgynous, asexual, or something else altogether. How much of our gender identity is tied to societal expectations and how much is due to our brain structure and chemistry is far from clear.

Unfortunately this book did a poor job of adding to the conversation. The author, a transgender woman with two sons who remains married to her sons birth mother, spends most of the book wrapped up in her own issues about how her transition affected her boys. The boys seems to be fine and more often than not annoyed with Maddy (the name they choose for their trans parent) because she keeps fussing about it. She pays some lip service to the effect all this had on her wife but doesn't really seem all that sympathetic. Since this is (at least) her second book on this topic I think she is a bit too self-involved. There is virtually no discussion of the larger picture of trans people in society. Perhaps this is because the author doesn't appear to have been affected n any major way by her transition. She has a good job, a loving family and accepting friends and relatives. Not at all the experience of many transgender people.

If you want something with a lot more nuance and depth, check out "This is How It Always Is" by Laurie Frankel.
Profile Image for Mell.
1,511 reviews16 followers
June 25, 2018
Full of good insights and some laugh-out-loud moments. Boylan is never afraid of admitting and spotlighting her humanity and flaws. She's relatable.

I found the author interview chapters a bit disruptive, and some were real duds for me. I most enjoyed the author's family interactions and discussions about gender non-conformity, kindness, and embracing life.
Profile Image for Rachel Brown.
68 reviews
April 8, 2024
I thought this book was so so sweet and gave such great real examples of love. I didn’t love the interviews in between, but opened my eyes to things I had never known. Everyone should be treated with love and respect and kindness 🤍
Profile Image for Kathy.
385 reviews
July 29, 2018
This is a memoir about Boylan’s transition from a man to a woman, while married and raising a family. The author wrote a previous book which contains more details about the transition itself. This book is about the impact this decision has on her family. Her wife stays with her once her transition to a woman is complete. The children seem to be adversely affected, but adopt a more open-minded view on the world.

The book is well-written and very interesting. I found Boylan’s reflections on parenthood and gender thought-provoking and very relevant. I loved her authentic communication style and would highly recommend this book.
Profile Image for Judy Blachek.
477 reviews3 followers
December 14, 2021
I really like the way that Jenny Finney Boylan writes. It's honest and genuine. I am sure I would like to have her family as friends as they seem warm, accepting, and smart.

The book is a reflection for JFB on whether her parenting changed after her transition. Basically the answer is no. She has the same traits and interests now as she did then and at one point commented after someone said they liked to bake that "you don't need a vagina to make cookies."

The book includes interviews with several other people -- some famous, some not as much -- but all friends with her. I found them interruptive of the flow of the book, but interesting at the same time. A separate book or article might have been better, but it did make some of her points, and it certainly made me reflect on my own parenting style.
Profile Image for Mary.
504 reviews3 followers
May 3, 2025
The interviews kept this book interesting. I felt like quite a bit of the rest was familiar from "She's Not There".
Profile Image for S.B. (Beauty in Ruins).
2,661 reviews239 followers
June 3, 2013
Although already an accomplished novelist at the time, it was the publication of She’s Not There: A Life in Two Genders in 2003 that first made Jennifer Finney Boylan a household name - and which firmly established gender issues as a topic of popular discussion in the process.

Says Jennifer of that seminal volume, “at first, I thought of She’s Not There as a kind of ‘once-off,’ after which I’d return to fiction. But, oddly, I hit some nerves with readers.” She found herself drawn to writing nonfiction, and since gender issues were very much at the centre of her life, it was inevitable that gender would become a topic she returned to again and again. “You could make a lot,” she muses, “if you wanted, out of the fact that as a man I wrote about things I had to invent, and as a woman I’ve been able to write about things that are true.“

Anybody who has ever given it even a moment’s passing thought knows that it is not easy to step outside the so-called ‘norm’ and embrace a gender identity or expression that lies beyond the traditional gender binary. There’s a world full of fear and prejudice out there, and the sad truth is we all too often have to accept the loss of friends and family in order to find peace and happiness within ourselves.

When there are children involved, however, the situation gets even more complex. Fortunately, Stuck in the Middle with You does a wonderful job of exploring the role that gender (and gender change) plays in parenting, and demonstrates that the health and happiness of one’s self and one’s children can coexist peacefully. That’s not to say it’s all fluff and laughter – there are some deep thoughts and some painful tears involved, but time, love, and caring heal most wounds.

When asked if, in writing about the lives of her children in Stuck in the Middle With You, she found herself at all sensitive to potentially negative reactions, Jennifer scoffs. “I think the only people who will react negatively . . . are people who have issues with trans people existing in the first place.”

As a second-time parent, going though the infant/toddler stage all over again, I was really struck by her doubts and fears regarding what secrets her boys might be hiding. I do wish we could have heard more from her children, and learned more about their rough edges, but it’s comforting to know that our children can take after us, and can learn from us, without actually becoming us.

An interesting aspect of Stuck in the Middle with You is the ‘Time Out’ Conversations with other parents that fall between the chapters. “I wanted to make the story about more than just me for a change,” says Jennifer, so she “turned to the moms and dads and “former children” that I knew, most of whom are writers, and asked them to talk to me about their own experience as parents, or about their own parents.”

At first I wasn’t sure what to think of those conversations, but I slowly began to see how their placement enhanced the story, adding a new perspective to things. The more we heard from other parents, the more it becomes clear that so many parenting experiences are universal, and not unique to any gender.

Jennifer takes the bold step of concluding the book with an interview of her partner and herself, conducted by novelist Anna Quindlen. Jennifer and Deirdre talk about stereotypes and secrets, about Maddy versus Daddy, and even answer a few difficult questions. It is Boylan, of course, who gets in the last word, but not before her partner has a chance to pull all the threads together in a family portrait that’s not much different from any other.

While not as ground-breaking as her first two novels, Stuck in the Middle with You is a welcome addition to the shelves upon shelves of parenting books out there, and one that offers a unique perspective for all genders.


Originally reviewed for Frock Magazine
Profile Image for Laurie.
973 reviews49 followers
January 10, 2014
Writer James Finney-Boylan had been a father for six years when he decided that he could no longer continue the charade of living as a man. She spent six years in the transition process, then underwent gender reassignment therapy and became a mother named Jennifer. She and her wife, Deirdre, remained married and raised their two sons as a couple. Jennifer has written her transition story elsewhere; this is the story of them as a family. Told in alternating sections by Jennifer and via interviews with other writers about family and raising children, we discover that Jennifer’s worries that her transition would damage the boys were unfounded: they are happy, well adjusted young men who do not think that their family is even slightly unusual. Amazingly, given how cruel kids (and adults) can be to anyone even slightly ‘different’, the boys were not bullied or maltreated by their schoolmates. She admits that her transition was very lucky because most of the many, many things that could have gone bad did not.

The book is an easy, interesting read. While I have read other transition stories, none have focused on the family like this one does. The interviews show that families and parenting styles come in all shapes and methods. This book adds a new facet to the huge array of parenting books. The only problem was a little bit of choppiness in the flow.
Profile Image for Melvin Marsh.
Author 1 book10 followers
February 5, 2018
When I read the blurb from Librarything Early Reviewers, I expected a book on being a transgender parent like I am as we have our own unique challenges. I am a female to male transsexual who is a parent and it is very difficult to raise a child when one is transgender. The book has a mixture of Jenny's own stories as well as interviews from other parents, most of which are very out of place. Of the interviews, only one was from another transsexual! I am not sure what Jenny was thinking when she added the interviews, I think they would have been better if they were in a separate book or perhaps even, if they had to be published, published in a journal article as they really did not add to any part of the book as they feel like "fluff."

Jenny's other book "She's not there" was a much better book not only about being transgender but also being a parent.
Profile Image for Gwen.
279 reviews
July 4, 2013
This book was wonderful, but I also found parts of it unspeakably sad.

At one point, I was reading it on the plane on the flight home from my 25th high school reunion and I had tears streaming down my face. I think the worst part was when Jenny was describing a Fourth of July celebration and what she most wanted was for Deedie to kiss her, and Deedie wouldn't... but she said "Don't be sad; I still love you". It was just awful. (Of course, that's my own issue creeping in...)

And I don't know, I guess it made me realize my failings as a parent. My inability to connect sometimes. My sadness, my depression, my dysphoria. It all gets in the way sometimes.

But it is a wonderful book.
61 reviews1 follower
April 1, 2014
The main narrative is really interesting and JFB is always entertaining and laces her writing with humor, but the interview interludes didn't really do it for me. They felt kind of like they were working backwards from a predetermined thesis which was being confirmed by the questions and answers. Or maybe I just didn't like how they interrupted the flow.
Profile Image for Holly.
1,172 reviews8 followers
August 5, 2015
This was almost too good to be a memoir. All the quotes, the things her family said over the years... they were almost too perfect. This was fascinating. The parenting stuff was particularly poignant because there was so much truth, whether you're experiencing parenthood as mother or father or a maddy.
Profile Image for Nat.
932 reviews10 followers
April 1, 2013
Won it in a goodreads giveaway. Interesting read to see how gender change effects on a family. Touching moments peppered with some funny moments. The only major flaw would be that the interviews break the flow of the book.
Profile Image for Matthew.
610 reviews16 followers
December 8, 2013
I didn't love the verbatim interview transcriptions, although they often had flashes of exceptional insight. I felt they would've been better integrated into Boylan's narrative, which was powerful -- in the sense of a necessary narrative -- and entertaining.
Profile Image for Janet.
2,255 reviews28 followers
May 20, 2013
Love Jennifer Finney Boylan--her writing and her acceptance of life as it is.
Profile Image for Jennifer Pletcher.
1,221 reviews7 followers
January 6, 2019
This is a memoir about the author who went through a transition from male to female. She was married and had two sons when she finally realized that she could not hide herself any longer. She talked with her wife, and when through the transition from Jimmy to Jenny. Her wife stayed with her and is still with her today. She went from being Daddy to Maddy to her boys. During her transition, her family faced a lot of challenges and many questions, but in the end, they stayed together as a family. This book tells her story, but also has interviews others in her life and examines their relationships with mothers, fathers, and children whether their own or as their roles of.



I thought this was a pretty good book. I would be lying if I was surprised that Jenny's wife stayed with her after her transition. Her wife does not identify as a lesbian, but she loves Jenny and loved their life, so she stuck with her. They seem like a well balanced, loving family. Their boys are grown now, and striving, and show no ill effects of Jenny's transition. I did enjoy the other interviews intermixed in this book - how people viewed their own relationships with their fathers, mothers and children. And how those relationships formed the person they are today.



I suggest reading it. There isn't a lot known or understood about people who are transgender, and I think this book gives a good insight on the struggles a person - and their family - can go through
Profile Image for Stephanie Sienkiewicz.
261 reviews1 follower
July 3, 2023
JFB always gets me thinking.

I have a particular soft spot for JFB, having been her student back in my undergrad days. Both having her as a professor and reading her memoir at the time were instrumental in beginning the work of interrogating gender and the rigid worldview I had been raised within.

This book strikes the same chord, but this time I got to read it as a parent myself. These concepts and structures - particularly family and gender - are somehow both complex and fundamental. I enjoyed reading both the memoir components and the interviews, even when the perspectives challenged my assumptions. Many of the interviewees have perspectives on parenting that don't align with my own neatly; some prompted me to examine my own and even expand my thinking, while others I was interested in exploring but not incorporating into mine. I think feeling simultaneously interested and unsettled by other people's viewpoints is a great practice - it reminds me just how many valid ways there are to be in the world.

The empathy and gentleness the entire Boylan family extends to the world are worth reading about and aspiring toward on their own. Everything else may be a bonus. There were a few times I got stuck and felt like the narrative slowed or repeated itself, but overall this was both enjoyable and edifying.
Profile Image for Ann Woodbury Moore.
792 reviews6 followers
August 25, 2020
Jennifer Finney Boylan, born James, transitioned from male to female 20 years ago. Her first autobiography, "She's Not There" (2003), chronicled her life through that point. "Stuck in the Middle With You" (2013) is a sequel, of sorts. Boylan describes her concerns at parenting her two sons and the effect her transition may have had on them. But she also includes three "Time Out" conversations with authors, artists and friends about fathers and sons, "waifs and angels," mothers and daughters. While interesting, I didn't find this book as gripping as "She's Not There." In addition--SPOILER ALERT--I learned that Boylan's older son recently transitioned from male to female. I would love to hear Boylan's honest reaction to this clearly unexpected event. She does at one point state that she would not want her sons to go through her experiences, because it's so difficult (in many ways--physically, emotionally, socially). Although of course in 2013 Boylan couldn't have anticipated the future, I feel that knowing what would happen could have dramatically changed her presentation.
Profile Image for Sherry.
1,828 reviews12 followers
November 16, 2021
I finished reading Jennie’s memoir, She’s Not Here: a memoir in Two Genders, and immediately started reading Stuck in the Middle with You. I’d just read Chris Bohjian’s Trans-Sister Radio for our Book discussion group next week and Boylan’s books were recommended. I have two others on hold at the library.

Both Bohjalian’s well researched, but fictional book and Boylan’s She’s Not Here gave me much insight into transgender people, their hopes, pain, struggles, and problems. Stuck in the Middle with You explores relationships between fathers, mothers, children through Jennie’s own story and a series of revealing interviews with diverse people including the very well known: Richard Russo, Edward Albee, and other voices not as familiar. What determine who we are, nature/nurture, experience- bad/good. What makes father/mother, masculine/feminine, gender or non/gender specific roles. Anna Quindlen explores how Jennie and Deedie’s experiences have affected their sons as they grew up. “Mandy” mommy/daddy, as Jennie is called by their sons, Zach and Sean explores parenting and childhood.
Profile Image for Carrie.
779 reviews12 followers
July 13, 2021
Finney Boylan, who was assigned male at birth and did not transition until after her two sons were born, describes herself as “a father for six years, a mother for ten, and for a time in between, neither, or both.” In this memoir, Finney Boylan explores her own experiences of parenthood and broader issues of what it means to be a mother/fact/parent and to what degree gender affects how we raise our children. The memoir is interspersed with Finney Boylan’s conversations with others about their experiences as children and as parents, and what they think family means. I really enjoyed this memoir— Finney Boylan is insightful and warm, and it gave me joy to hear her reflections on life raising her children as I am at the beginning of my own journey as a mother.
Profile Image for Mary Beth.
74 reviews4 followers
May 28, 2024
What a chopped up mess!

My adult child, whom I dearly love, is trans so I’m trying to understand them better. I already love and accept them, but I just want to get a trans perspective. I think the amount of original material about Jenny’s life could have been a blog or magazine article. The interviews were just ridiculous. Another reviewer called it “lazy writing.” I agree. They are just transcripts of a podcast. It feels like an advertisement for her podcast. Plus, what was the point of including them? They just interrupted the narrative. A couple of the interviews didn’t seem to have relevance on the topic, imho. Maybe I would have appreciated it more if I had read her first memoir.
Profile Image for Nana.
885 reviews15 followers
May 6, 2025
The journey of life in your 40s. Becca and Niamh are best friends and now they are women of that certain age. Becca's new job is sending her on a weekend retreat, so she takes Niamh and another friend along. It was nothing like they expected, but they did learn a lot, got some insight, and made some decisions for themselves. They needed to think about themselves, do things for themselves sometimes, and life could be exciting at any age. Whether it be 16 or in their 40s. They share with us from the women of a certain age to who they became after going to the weekend retreat, and thinking about what they wanted to get out of life. It was a fabulous story.
I received an ARC from Boldwood Books through NetGalley.
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