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Stuck in the Middle with You

A Memoir of Parenting in Three Genders

Contributions by Anna Quindlen
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On sale Apr 22, 2014 | 320 Pages | 978-0-7679-2177-0
| Grades 9-12 + AP/IB
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New York Times bestselling author Jennifer Finney Boylan returns with a remarkable memoir about gender and parenting that discusses how families are shaped and the difficulties and wonders of being human.
 
A father for six years, a mother for ten, and for a time in between, neither, or both, 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. 

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 between fathers, mothers, and children; people's memories of the children they were and the parents they became; and the many different ways a family can be. With an Afterword by Anna Quindlen, Stuck in the Middle with You is a brilliant meditation on raising—and on beinga child.

Now with Extra Libris material, including a reader’s guide and bonus content
Red Card

She sat alone in the stands as the duel unfolded. Like me, she had no visible husband. I had a lump in my breast. She seemed sad. Our sons had swords.

I slid next to her on the bleacher, put my purse on the floor. Then a group of dads two rows ahead of us leapt to their feet, yelling. A boy was on the ground. His adversary stood above him, foil extended.

“Red card!” shouted one of the dads. “Red-card him, ref!”

The trainer from my sons’ school, Kents Hill, stepped toward the ring to protest. But a penalty was not called.

“Are you blind, ref?” shouted one of the dads. He was really upset. I’d never seen a dad all red in the face at a fencing match before.

“They don’t understand,” said the woman to my right. She was a tiny thing, like a budgie. In her hands she held a copy of Cooking Light magazine. “He was flèching him.”

“Fleshing?” I said. A lot of the minutiae of fencing was beyond me. Offhand this sounded like the word you’d use if you accidentally encouraged someone to wind up naked.

“Flèche,” she said. “That’s Ethan’s secret weapon.”

The dads in front of us were still hollering and booing. The boy who’d been upended was back on his feet, and now I recognized him. This was a young man we’ll call Chandler, the smallest boy on the Kents Hill team.

His adversary did a merciless ninth-grade equivalent of Muhammad Ali’s victory dance. I am the greatest. His facial expression wasn’t visible, what with the mask, but it wasn’t hard to imagine.

“That’s your son?”

She nodded.

“I’m Jenny Boylan?” I said.

“Grenadine Phelps?” she said. It would have been nice to be able to say that this was the first time I’d met a woman named after a liquor, but in Maine, there’s a long-standing tradition of naming people after bottles of alcohol. I’d known a Brandy, a Bacardi, and a couple of Sherrys. Brandy had once cornered me in the ladies’ room at a blues bar where my band was playing and tried to get me to make out with her. Things like that happened to me more than you’d expect, which at first I’d thought was just my own rotten luck but which lately I’d begun to worry was my fault. On another occasion, for example, I’d accidentally wound up at a convention of ventriloquists, in Kentucky. There’d been this whole scene with this one guy who kept coming on to me using his “muffle voice.”

The boys began to fence again, the gigantic Ethan and the tiny, terrified Chandler. Once again, Ethan charged at him, yelling as he advanced like one of the riders of Rohan: “Deaath!” He whacked Chandler’s sword and it flew out of the boy’s hand and skittered away on the gym floor.

“Flèched him again,” said Grenadine wearily, as if irritated that Chandler had not learned that her son only had one trick, and that this was it.

“I’m sorry, what’s flèching? You mean that charging thing?”

“Yeah,” said Grenadine. “You extend the arm and pounce. Ethan’s known for his flèche.”

Yeah, well, I thought, Chandler’s known for going to the bathroom in his actual pants.

The coach was now out talking to Chandler, who had his mask off. He was sniffing back the tears.

Another boy, an elegant and graceful young thing, picked up the fallen sword and returned it to Chandler with a small bow. He had hair halfway down his back, a huge cascade of blond curls tied in a braid. He patted Chandler on the shoulder, whispered something encouraging to him. Buck up.

“Jeez, look at the hair on that kid,” said Grenadine.

“He’s got hair all right,” I said. My son Zach was admired for his hair in the same way her son Ethan was known for stabbing people.

But before I could explain this, Grenadine said, “My husband would never allow Ethan to have hair like that. He’d send him to military school first.”

I shrugged. I didn’t feel like defending Zach to a stranger. Was that really what I was here for, a conversation about hair?

Chandler had his mask on again and was back in the ring—more properly known as the piste, or strip. Zach stood to one side, watching the boy. He was the team co-captain.

“Kid looks like a girl,” said Grenadine. The way she said it, it didn’t sound like a compliment.

Zach looked like a lot of things, but a girl was not one of them, unless you were the kind of person who believed long hair woman, short hair man. He was tall and broad shouldered, my boy. The hair had made Zach very popular. There were a number of girls—some of them on the fencing team, in fact—who liked to do the braid. It was fairly obvious how much they all adored Zach. It wasn’t obvious to him though.

Below us, Ethan extended his arm and went charging down upon little Chandler again. But this time, Chandler parried and then seized right-of-way. He came forward with the riposte and scored a hit off Ethan.

The dads below me shouted their approval. “Atta boy, Chandler!” they yelled. “Push back on him! Slay him!”

“Oh, honestly,” said Grenadine.

The boys were now eyeing each other warily. They moved first one way, then the other, looking for an opening. You could feel the tension between them, Ethan looking for another chance to use his trick, Chandler emboldened by the hit he’d scored. There wasn’t much chance that Chandler was going to win this match, but you had to give him credit for staying in the game. Very quietly, I began to hope some not-particularly-terrible thing might happen to Ethan, like the roof collapsing, or the boy’s having a tiny nonlethal coronary.

At the edge of the strip, my son Zach stood there watching his teammate’s progress. The men below me shouted again.

“It’s a good thing my husband’s not here,” she said, listening to the hecklers.

“How come?” I asked.

She sighed. “There’d be trouble.”

“Does he come to a lot of the matches? Your husband?”

“Oh, no.” There was a slight pause. Then she said, “He’s in Iraq.”

Ethan got another touch on Chandler, and the dads below me moaned. One of them—was it Chandler’s father?—held his head in his hands, as if he’d been called upon to witness his own son’s execution for crimes against the state.

“That must be hard,” I said.

She pulled into herself and did not respond. For a second it seemed almost as if the stranger were trying to hold back tears.

“It’s better with him gone,” she said, in a voice that was almost a whisper.

“Seriously?”

She nodded, and a tear brimmed over one of her lashes.

“Sometimes I hope he never comes back,” she said. “Sometimes I wish he’d get—”

Gazing upon the gigantic, merciless Ethan below me, I wondered if I could begin to imagine Grenadine’s married life. I pictured a menacing Ethan Senior bearing down upon the tiny, birdlike Grenadine Phelps, and winced. Junior had learned that pouncing trick from somewhere, and it wasn’t his mom.

She eyed the wedding ring on my finger. “What about you? Where’s yours?”

And just like that, I found myself in one of those situations where neither telling the truth nor coming up with a great big lie was going to accomplish anything. What could I say to her? Well, actually, I’m transgender. I used to be a man, but I’ve been a woman for ten years now. I’m still married to the woman I married twenty-five years ago, back when I was a man. Crazy vorld, huh? Ha! Ha! Ha!

Wow, she’d reply. Isn’t your marriage really screwed up then?

I thought about Grenadine’s marriage and my own. People looking at my wife, Deedie, and me—two women, not lesbians, legally married to each other—would say we were insane, way out of the mainstream, a threat to traditional American values. And all that. Whereas Grenadine and Ethan Senior were a paragon of all we revere: a heterosexual married couple, a dad serving his country in the war overseas. By almost anyone’s measure, Deedie and I are the dangerous outliers, and Grenadine and her husband Mr. and Mrs. Normal. Even though Deedie and I love each other beyond all understanding, and Grenadine’s fondest hope was that her husband would be murdered by insurgents.

Sometimes I don’t understand the world at all, is my conclusion.

“I don’t have a husband right now,” I said to Grenadine. I was satisfied by the ambiguity of this, although it had to be admitted that this too was kind of a lie—since it implied that I’d once had one, or that a day would come when I might.

Down on the floor below us, Ethan hollered as he charged toward Chandler for the match point. The enormous creature bearing down upon the tiny, frightened boy was terrible to behold. Chandler dropped his sword again and raised his hands toward his mask. Ethan wonked him on the chest, and the electronic touch detector—which was automatically scoring the event—registered the hit. Ethan had vanquished Chandler. They took off their masks and shook hands.

“Atta boy, Chandler,” shouted his dad. “Way to show character!”

Grenadine rolled her eyes. “Character,” she muttered sadly, as if this were something she had heard about once.

Ethan searched the stands and saw his mother there, and then he nodded at her. He had a crew cut and an ingrown smirk.

My own son patted Chandler on the back. Looking down at my boy, I had a strange, nostalgic feeling—wishing that, when I’d been a guy, I’d had half the character now exhibited by my own near-grown son. It’s common enough, I guess, a thought such as this, demented though it may be. We look to our children as a kind of cosmic mulligan, our own best hope for a second chance. There were plenty of times I had looked at my son Zach as a better version of me, man-wise. He had the same goofy sense of humor, the same habit of wearing his heart right out there on his sleeve where anyone could crush it, the same buoyant hope that somehow love would prevail over all.

If I had failed as a man—and even those people who loved me most would have to admit this, what with the vagina and everything—then maybe Zach was a last chance to get it right. The man that I had once been clearly lived in him, although this time around we seemed to have been spared the melancholic lunacy.

On the other hand, I knew full well that thinking in this way was a surefire path to frustration. Children are here to live their own lives, not ours, and any parent who looks to her son to right the wrongs of her own past probably ought to get out of the parenting business entirely.

“I’m sorry I said that,” said the tiny Grenadine. “About my husband. You must think I’m a basket case.”

“Of course not,” I said. “I knew you didn’t mean it.”

“But I did mean it,” she said, after a pause.

“Seriously?”

“He’s just not a nice guy,” she said. “The army changed him.”

I shrugged. “People change,” I said. Coming from me, this was an understatement.

Something throbbed in my left breast. It wasn’t sentiment. An odd, pulsing pain had been lurking in me for a month or two. I’d been doing a self-exam in a shower in a hotel in New York back in December when I’d first found the lump. Incredibly, I’d tried to pretend it wasn’t there for the first month or so. But every time I felt for it to see if it was still there, I found it, larger. A mammogram was scheduled for the next day, the morning after the fencing tournament.

I’d begun to do some of the math in my head. Having seen my own father, and then my sister-in-law, slain by cancer, suffering through the chemo and the radiation, and the surgery, only to die agonizing deaths, I’d already decided, if it was cancer I wasn’t doing any of that. I’d just go to the zoo and jump into the lions’ cage instead.

It wasn’t that I didn’t love my life—the opposite, in fact. As someone who’d lived a full life as a man, then survived the perilous transition and then lived another ten euphoric years as a woman, I had plenty of things to be grateful for. Quite frankly, I couldn’t imagine anyone’s having had such a lucky life as my own, in spite of all the tears my condition—and the effects that it had had on others—had engendered. I’d been married for almost twenty-five years to a woman I adored, and who still adored me. I’d had what felt—at times—like the best job in the world, teaching English at Colby. I’d written a bestselling book, been a guest of Oprah Winfrey, even been imitated on Saturday Night Live by Will Forte, who, according to some people, did a better impression of me than I did.

I had two brilliant and resilient sons, each of them with amazing and fabulous hair.

Quite frankly, there wasn’t a whole lot left on my to-do list. Other than sit back in wonder and see what happens next.

“I hate that,” said Grenadine softly. “I hate it, that people change.”

I was a father for six years, a mother for ten, and for a time in between I was both, or neither, like some parental version of the schnoodle, or the cockapoo. Of course, as parents go, I was a rather feminine father; for that matter I suppose I’m a masculine mother. When I was their father I showed my boys how to make a good tomato sauce, how to fold a napkin, how to iron a dress shirt; as their mother I’ve shown them how to split wood with a maul. Whether this means I’ve had one parenting style or two, I am not entirely certain. I can assure you I am not a perfect parent and will be glad to review the long list of my mistakes. But in dealing with a parent who subverts a lot of expectations about gender, I hope my sons have learned to be more flexible and openhearted than many of their peers with traditionally gendered parents.

I would like to think that this has been a gift to them and not a curse. It is my hope that having a father who became a woman has made my two remarkable boys, in turn, into better men.
  • FINALIST | 2014
    Triangle Literary Award
Stuck in the Middle also comes with vivid observations....Boylan remains a role model for her brisk prose and her high spirits as well as for her public advocacy and attention to her wife and their sons.” Los Angeles Times

“Parents will recognize the basics here: The days go on forever; the years fly by; the heart is gripped by an aching, terrified love. The fact that Boylan changes her gender along the way—father of babies becomes mother of teenagers—does not make this memoir a cabinet of curiosities. It’s a family love story, bighearted and fearlessly funny. ‘To accept the wondrous scope of gender,’ Boylan writes, ‘is to affirm the vast potential of life, in all its messy, unfathomable beauty.’ And her story, interspersed with celebrity interviews on parenting, is messy and beautiful indeed. In the end...as Boylan’s mother puts it, ‘love will prevail.’” More Magazine

“[A] warm, engaging memoir...This informal investigation and her touchingly funny and always candid story work together to reveal the book’s ultimate truth: that ‘to accept the wondrous scope of gender is to affirm the vast potential of life in all its messy, unfathomable beauty’...Genuinely insightful through and through.” Kirkus

“Boylan illuminates diverse family relationships and the many ways families operate fluidly on a seemingly never-ending spectrum. This unique and giving book has tremendous resonance.” Booklist

“Boylan enlists different perspectives by writers and others to explore in depth how parenting involves much more than birthing...Boylan records in engaging short narratives her complicated process of evolving as a parent, from being a father (“Jim”) for six years, a mother for 10, and throughout embracing a ‘flexible’ and ‘openhearted’ approach that has proven remarkably successful and long-lasting. Boylan writes honestly about the enormous toll her transitioning took on the family, the sense of ‘loss’ they all suffered when she became a woman in 2000, the anxieties she and Deedee felt over the children’s reaction to public censure, dread that the kids harbored their own dark secrets, and annoyance at other people’s inability to use the right pronoun.” Publishers Weekly

“No other memoirist I’ve read so perfectly blends intimacy and witty remove, soul-searching and slapstick, joy and pain. As a child—or as a reader—one could not ask for a wiser, warmer, more engaging companion than Jennifer Finney Boylan.” —Mary Roach, author of Stiff and Packing for Mars
© Jim Bowdoin
Jennifer Finney Boylan is the bestselling author of more than a dozen books. She is the inaugural Anna Quindlen Writer-in-Residence at Barnard College of Columbia University and a 2022–2023 Fellow at Harvard University’s Radcliffe Institute for Advanced Study. A nationally known advocate for human rights, she is a trustee of PEN America. For many years she was the national co-chair of GLAAD as well as a contributing opinion writer for The New York Times. She lives in New York City and Belgrade Lakes, Maine, with her wife, Deedie. They have a son, Sean, and a daughter, Zai. View titles by Jennifer Finney Boylan
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About

New York Times bestselling author Jennifer Finney Boylan returns with a remarkable memoir about gender and parenting that discusses how families are shaped and the difficulties and wonders of being human.
 
A father for six years, a mother for ten, and for a time in between, neither, or both, 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. 

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 between fathers, mothers, and children; people's memories of the children they were and the parents they became; and the many different ways a family can be. With an Afterword by Anna Quindlen, Stuck in the Middle with You is a brilliant meditation on raising—and on beinga child.

Now with Extra Libris material, including a reader’s guide and bonus content

Excerpt

Red Card

She sat alone in the stands as the duel unfolded. Like me, she had no visible husband. I had a lump in my breast. She seemed sad. Our sons had swords.

I slid next to her on the bleacher, put my purse on the floor. Then a group of dads two rows ahead of us leapt to their feet, yelling. A boy was on the ground. His adversary stood above him, foil extended.

“Red card!” shouted one of the dads. “Red-card him, ref!”

The trainer from my sons’ school, Kents Hill, stepped toward the ring to protest. But a penalty was not called.

“Are you blind, ref?” shouted one of the dads. He was really upset. I’d never seen a dad all red in the face at a fencing match before.

“They don’t understand,” said the woman to my right. She was a tiny thing, like a budgie. In her hands she held a copy of Cooking Light magazine. “He was flèching him.”

“Fleshing?” I said. A lot of the minutiae of fencing was beyond me. Offhand this sounded like the word you’d use if you accidentally encouraged someone to wind up naked.

“Flèche,” she said. “That’s Ethan’s secret weapon.”

The dads in front of us were still hollering and booing. The boy who’d been upended was back on his feet, and now I recognized him. This was a young man we’ll call Chandler, the smallest boy on the Kents Hill team.

His adversary did a merciless ninth-grade equivalent of Muhammad Ali’s victory dance. I am the greatest. His facial expression wasn’t visible, what with the mask, but it wasn’t hard to imagine.

“That’s your son?”

She nodded.

“I’m Jenny Boylan?” I said.

“Grenadine Phelps?” she said. It would have been nice to be able to say that this was the first time I’d met a woman named after a liquor, but in Maine, there’s a long-standing tradition of naming people after bottles of alcohol. I’d known a Brandy, a Bacardi, and a couple of Sherrys. Brandy had once cornered me in the ladies’ room at a blues bar where my band was playing and tried to get me to make out with her. Things like that happened to me more than you’d expect, which at first I’d thought was just my own rotten luck but which lately I’d begun to worry was my fault. On another occasion, for example, I’d accidentally wound up at a convention of ventriloquists, in Kentucky. There’d been this whole scene with this one guy who kept coming on to me using his “muffle voice.”

The boys began to fence again, the gigantic Ethan and the tiny, terrified Chandler. Once again, Ethan charged at him, yelling as he advanced like one of the riders of Rohan: “Deaath!” He whacked Chandler’s sword and it flew out of the boy’s hand and skittered away on the gym floor.

“Flèched him again,” said Grenadine wearily, as if irritated that Chandler had not learned that her son only had one trick, and that this was it.

“I’m sorry, what’s flèching? You mean that charging thing?”

“Yeah,” said Grenadine. “You extend the arm and pounce. Ethan’s known for his flèche.”

Yeah, well, I thought, Chandler’s known for going to the bathroom in his actual pants.

The coach was now out talking to Chandler, who had his mask off. He was sniffing back the tears.

Another boy, an elegant and graceful young thing, picked up the fallen sword and returned it to Chandler with a small bow. He had hair halfway down his back, a huge cascade of blond curls tied in a braid. He patted Chandler on the shoulder, whispered something encouraging to him. Buck up.

“Jeez, look at the hair on that kid,” said Grenadine.

“He’s got hair all right,” I said. My son Zach was admired for his hair in the same way her son Ethan was known for stabbing people.

But before I could explain this, Grenadine said, “My husband would never allow Ethan to have hair like that. He’d send him to military school first.”

I shrugged. I didn’t feel like defending Zach to a stranger. Was that really what I was here for, a conversation about hair?

Chandler had his mask on again and was back in the ring—more properly known as the piste, or strip. Zach stood to one side, watching the boy. He was the team co-captain.

“Kid looks like a girl,” said Grenadine. The way she said it, it didn’t sound like a compliment.

Zach looked like a lot of things, but a girl was not one of them, unless you were the kind of person who believed long hair woman, short hair man. He was tall and broad shouldered, my boy. The hair had made Zach very popular. There were a number of girls—some of them on the fencing team, in fact—who liked to do the braid. It was fairly obvious how much they all adored Zach. It wasn’t obvious to him though.

Below us, Ethan extended his arm and went charging down upon little Chandler again. But this time, Chandler parried and then seized right-of-way. He came forward with the riposte and scored a hit off Ethan.

The dads below me shouted their approval. “Atta boy, Chandler!” they yelled. “Push back on him! Slay him!”

“Oh, honestly,” said Grenadine.

The boys were now eyeing each other warily. They moved first one way, then the other, looking for an opening. You could feel the tension between them, Ethan looking for another chance to use his trick, Chandler emboldened by the hit he’d scored. There wasn’t much chance that Chandler was going to win this match, but you had to give him credit for staying in the game. Very quietly, I began to hope some not-particularly-terrible thing might happen to Ethan, like the roof collapsing, or the boy’s having a tiny nonlethal coronary.

At the edge of the strip, my son Zach stood there watching his teammate’s progress. The men below me shouted again.

“It’s a good thing my husband’s not here,” she said, listening to the hecklers.

“How come?” I asked.

She sighed. “There’d be trouble.”

“Does he come to a lot of the matches? Your husband?”

“Oh, no.” There was a slight pause. Then she said, “He’s in Iraq.”

Ethan got another touch on Chandler, and the dads below me moaned. One of them—was it Chandler’s father?—held his head in his hands, as if he’d been called upon to witness his own son’s execution for crimes against the state.

“That must be hard,” I said.

She pulled into herself and did not respond. For a second it seemed almost as if the stranger were trying to hold back tears.

“It’s better with him gone,” she said, in a voice that was almost a whisper.

“Seriously?”

She nodded, and a tear brimmed over one of her lashes.

“Sometimes I hope he never comes back,” she said. “Sometimes I wish he’d get—”

Gazing upon the gigantic, merciless Ethan below me, I wondered if I could begin to imagine Grenadine’s married life. I pictured a menacing Ethan Senior bearing down upon the tiny, birdlike Grenadine Phelps, and winced. Junior had learned that pouncing trick from somewhere, and it wasn’t his mom.

She eyed the wedding ring on my finger. “What about you? Where’s yours?”

And just like that, I found myself in one of those situations where neither telling the truth nor coming up with a great big lie was going to accomplish anything. What could I say to her? Well, actually, I’m transgender. I used to be a man, but I’ve been a woman for ten years now. I’m still married to the woman I married twenty-five years ago, back when I was a man. Crazy vorld, huh? Ha! Ha! Ha!

Wow, she’d reply. Isn’t your marriage really screwed up then?

I thought about Grenadine’s marriage and my own. People looking at my wife, Deedie, and me—two women, not lesbians, legally married to each other—would say we were insane, way out of the mainstream, a threat to traditional American values. And all that. Whereas Grenadine and Ethan Senior were a paragon of all we revere: a heterosexual married couple, a dad serving his country in the war overseas. By almost anyone’s measure, Deedie and I are the dangerous outliers, and Grenadine and her husband Mr. and Mrs. Normal. Even though Deedie and I love each other beyond all understanding, and Grenadine’s fondest hope was that her husband would be murdered by insurgents.

Sometimes I don’t understand the world at all, is my conclusion.

“I don’t have a husband right now,” I said to Grenadine. I was satisfied by the ambiguity of this, although it had to be admitted that this too was kind of a lie—since it implied that I’d once had one, or that a day would come when I might.

Down on the floor below us, Ethan hollered as he charged toward Chandler for the match point. The enormous creature bearing down upon the tiny, frightened boy was terrible to behold. Chandler dropped his sword again and raised his hands toward his mask. Ethan wonked him on the chest, and the electronic touch detector—which was automatically scoring the event—registered the hit. Ethan had vanquished Chandler. They took off their masks and shook hands.

“Atta boy, Chandler,” shouted his dad. “Way to show character!”

Grenadine rolled her eyes. “Character,” she muttered sadly, as if this were something she had heard about once.

Ethan searched the stands and saw his mother there, and then he nodded at her. He had a crew cut and an ingrown smirk.

My own son patted Chandler on the back. Looking down at my boy, I had a strange, nostalgic feeling—wishing that, when I’d been a guy, I’d had half the character now exhibited by my own near-grown son. It’s common enough, I guess, a thought such as this, demented though it may be. We look to our children as a kind of cosmic mulligan, our own best hope for a second chance. There were plenty of times I had looked at my son Zach as a better version of me, man-wise. He had the same goofy sense of humor, the same habit of wearing his heart right out there on his sleeve where anyone could crush it, the same buoyant hope that somehow love would prevail over all.

If I had failed as a man—and even those people who loved me most would have to admit this, what with the vagina and everything—then maybe Zach was a last chance to get it right. The man that I had once been clearly lived in him, although this time around we seemed to have been spared the melancholic lunacy.

On the other hand, I knew full well that thinking in this way was a surefire path to frustration. Children are here to live their own lives, not ours, and any parent who looks to her son to right the wrongs of her own past probably ought to get out of the parenting business entirely.

“I’m sorry I said that,” said the tiny Grenadine. “About my husband. You must think I’m a basket case.”

“Of course not,” I said. “I knew you didn’t mean it.”

“But I did mean it,” she said, after a pause.

“Seriously?”

“He’s just not a nice guy,” she said. “The army changed him.”

I shrugged. “People change,” I said. Coming from me, this was an understatement.

Something throbbed in my left breast. It wasn’t sentiment. An odd, pulsing pain had been lurking in me for a month or two. I’d been doing a self-exam in a shower in a hotel in New York back in December when I’d first found the lump. Incredibly, I’d tried to pretend it wasn’t there for the first month or so. But every time I felt for it to see if it was still there, I found it, larger. A mammogram was scheduled for the next day, the morning after the fencing tournament.

I’d begun to do some of the math in my head. Having seen my own father, and then my sister-in-law, slain by cancer, suffering through the chemo and the radiation, and the surgery, only to die agonizing deaths, I’d already decided, if it was cancer I wasn’t doing any of that. I’d just go to the zoo and jump into the lions’ cage instead.

It wasn’t that I didn’t love my life—the opposite, in fact. As someone who’d lived a full life as a man, then survived the perilous transition and then lived another ten euphoric years as a woman, I had plenty of things to be grateful for. Quite frankly, I couldn’t imagine anyone’s having had such a lucky life as my own, in spite of all the tears my condition—and the effects that it had had on others—had engendered. I’d been married for almost twenty-five years to a woman I adored, and who still adored me. I’d had what felt—at times—like the best job in the world, teaching English at Colby. I’d written a bestselling book, been a guest of Oprah Winfrey, even been imitated on Saturday Night Live by Will Forte, who, according to some people, did a better impression of me than I did.

I had two brilliant and resilient sons, each of them with amazing and fabulous hair.

Quite frankly, there wasn’t a whole lot left on my to-do list. Other than sit back in wonder and see what happens next.

“I hate that,” said Grenadine softly. “I hate it, that people change.”

I was a father for six years, a mother for ten, and for a time in between I was both, or neither, like some parental version of the schnoodle, or the cockapoo. Of course, as parents go, I was a rather feminine father; for that matter I suppose I’m a masculine mother. When I was their father I showed my boys how to make a good tomato sauce, how to fold a napkin, how to iron a dress shirt; as their mother I’ve shown them how to split wood with a maul. Whether this means I’ve had one parenting style or two, I am not entirely certain. I can assure you I am not a perfect parent and will be glad to review the long list of my mistakes. But in dealing with a parent who subverts a lot of expectations about gender, I hope my sons have learned to be more flexible and openhearted than many of their peers with traditionally gendered parents.

I would like to think that this has been a gift to them and not a curse. It is my hope that having a father who became a woman has made my two remarkable boys, in turn, into better men.

Awards

  • FINALIST | 2014
    Triangle Literary Award

Praise

Stuck in the Middle also comes with vivid observations....Boylan remains a role model for her brisk prose and her high spirits as well as for her public advocacy and attention to her wife and their sons.” Los Angeles Times

“Parents will recognize the basics here: The days go on forever; the years fly by; the heart is gripped by an aching, terrified love. The fact that Boylan changes her gender along the way—father of babies becomes mother of teenagers—does not make this memoir a cabinet of curiosities. It’s a family love story, bighearted and fearlessly funny. ‘To accept the wondrous scope of gender,’ Boylan writes, ‘is to affirm the vast potential of life, in all its messy, unfathomable beauty.’ And her story, interspersed with celebrity interviews on parenting, is messy and beautiful indeed. In the end...as Boylan’s mother puts it, ‘love will prevail.’” More Magazine

“[A] warm, engaging memoir...This informal investigation and her touchingly funny and always candid story work together to reveal the book’s ultimate truth: that ‘to accept the wondrous scope of gender is to affirm the vast potential of life in all its messy, unfathomable beauty’...Genuinely insightful through and through.” Kirkus

“Boylan illuminates diverse family relationships and the many ways families operate fluidly on a seemingly never-ending spectrum. This unique and giving book has tremendous resonance.” Booklist

“Boylan enlists different perspectives by writers and others to explore in depth how parenting involves much more than birthing...Boylan records in engaging short narratives her complicated process of evolving as a parent, from being a father (“Jim”) for six years, a mother for 10, and throughout embracing a ‘flexible’ and ‘openhearted’ approach that has proven remarkably successful and long-lasting. Boylan writes honestly about the enormous toll her transitioning took on the family, the sense of ‘loss’ they all suffered when she became a woman in 2000, the anxieties she and Deedee felt over the children’s reaction to public censure, dread that the kids harbored their own dark secrets, and annoyance at other people’s inability to use the right pronoun.” Publishers Weekly

“No other memoirist I’ve read so perfectly blends intimacy and witty remove, soul-searching and slapstick, joy and pain. As a child—or as a reader—one could not ask for a wiser, warmer, more engaging companion than Jennifer Finney Boylan.” —Mary Roach, author of Stiff and Packing for Mars

Author

© Jim Bowdoin
Jennifer Finney Boylan is the bestselling author of more than a dozen books. She is the inaugural Anna Quindlen Writer-in-Residence at Barnard College of Columbia University and a 2022–2023 Fellow at Harvard University’s Radcliffe Institute for Advanced Study. A nationally known advocate for human rights, she is a trustee of PEN America. For many years she was the national co-chair of GLAAD as well as a contributing opinion writer for The New York Times. She lives in New York City and Belgrade Lakes, Maine, with her wife, Deedie. They have a son, Sean, and a daughter, Zai. View titles by Jennifer Finney Boylan

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