Transgender Author Jennifer Finney Boylan Went From Dad to Mom: How it Changed Her Family

Boylan with sons Sean and Zachary and wife Deedie. Photo: Courtesy Jenny BoylanThere are not too many people in the world who can say they’ve been both a mother and a father. But Jennifer Finney Boylan, née James Boylan, can.

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As James—a dark-haired man with a “feminine streak” who was a teacher of literature and a fan of Grateful Dead music—he met and fell in love with his wife, Deedie, in his late twenties, and soon became a father to their two sons. But James was harboring a secret: He was transgender, and, in his heart, had never truly felt male. He suppressed the notion for several years after marrying Deedie, but it eventually racked him with debilitating anger and sadness.

“I used to tear my hair out thinking, when you have children, you’re not only living for yourself,” Boylan told Yahoo! Shine in an interview this week. “I was willing to bear a pretty heavy burden that meant keeping the people around me safe, but I got to the point where I couldn’t take another step living a life of falsehood.”

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And so, beginning when his sons Sean (now 17) and Zachary (now 19) were about 3 and 5 years old, James, with Deedie’s eventual blessing, began the major, at times heart-wrenching transition to become Jenny. It was a four-year process that began with a difficult conversation with Deedie when James was 44, and culminated with surgery to become a fully physically female (Though the “transition doesn’t end with surgery. And surgery is not the most important thing,” she stresses). Boylan wrote about her transition in what became a best-selling 2003 memoir, “She’s Not There,” landing her on Oprah and making her one of the most recognizable trans individuals in the country.

Now the professor of English at Colby College in Maine and author of a dozen books has published a follow-up to that memoir, “Stuck in the Middle with You: A Memoir of Parenting in Three Genders,” exploring what it means to have been a father for 6 years, a mother for 10, and, “for a time in between, neither, or both.” Woven between the chapters of her personal family stories are illuminating interviews about parenthood and childhood, with folks including fellow writers Edward Albee, Augusten Burroughs and Susan Minot. The complete package is a groundbreaking look at what it means to be a mother, or a father, and what differences there are, if any, anymore.

As a father, Boylan was more “goofy” and playful. As a mother, she told Shine, “I helicopter over them more than I used to,” because now, as a woman, “I’m aware of the vulnerability of people, I’m aware of the danger. I’ve been at risk in the world, so that means I know the risks that other people face.”

The Boylan family. Photo: Courtesy of Jenny BoylanBut, in general, she stressed, the gender of parents turns out to not be of utmost importance at this point in time. “So you can look at a heteronormative family, you can look at two moms, two dads, single moms, single dads, adoptive families. There are so many ways to be a family, and none of that matters as much as the love that’s in that family,” she explained. “That shouldn’t be a revolutionary thing to say, but I think it is, in certain circles.”

The love in Boylan’s family clearly runs deep. When she began her transition, Jenny and her wife “cried, like, every day for two years,” she recalls, “just beside ourselves with loss.” Eventually, though, she said they “realized that what we were going to keep was more important than what we’d lost.” They decided to stay married—it’s now been 25 years—but there have been complications, as Jenny identifies as a lesbian and Deedie does not.

“It does mean that we each want different things in a sexual relationship, so that’s awkward,” Boylan admitted. “We are two women who love each other who are raising children that are our biological children. We sleep in the same bed. We adore each other.” And, while noting that sexual intimacy is not the only form of intimacy in a long marriage, she does add, “I don’t mean to downplay the importance of sex, because I love sex, and the absence of sex makes me feel mournful and hollow sometimes. Makes each of us feel that way. But anyone who judges our relationship only by that is totally missing the point.”

The love and understanding exhibited by their sons is also pretty powerful. In the book, Boylan writes about how Sean and Zachary come to accept the transformation of father to mother with a gentle, intelligent wisdom—how they decided to call her “Maddy,” since it was a nice combo of Mom and Daddy, how they confided in her about growing pains as they grew into young men, and how they even kept her in check, from time to time, about being true to herself. In fact, when Boylan told the family she was going to write another memoir, it was Zach who said, “OK, fine. But if you’re going to write about us, could you use our real names this time?”

When asked what they must have done as parents to raise such understanding sons, Boylan said they had done things both consciously—reading to them every day, encouraging imagination, having a sense of humor, sitting down to meals together—and unconsciously, that she hopes have made their mark. For examples of the latter, she explained, “Just by having such a curious other mother, my sons have had to learn to be compassionate and open-hearted. And I think they’ve come to be more sympathetic to all the world’s outliers and outcasts, because they know what it’s like to be among people who are different, who have big hearts and big souls, and who are full of love. And who are nonetheless vulnerable in the world as a result.”

At one point during this interview, Deedie and Zach paid a visit, and Deedie added to Jenny’s estimation. “Our speculation is that we were never ashamed of anything,” she said. “Plus they’re cool kids who always had cool friends.”

Zach, an open-faced, handsome young man with tousled brown curls, talked a bit about having a family life that was under so much public scrutiny. “I’ve just sort of grown up with it, and grown used to it,” he explained. “And also just, in this day and age, with Facebook and social media, people are already putting themselves out there without having a semi-famous parent. So I mean, it’s not something that troubles me. I grew up with it.” Then Boylan chimed in with the story about Zach requesting she write with their real names, and said to him, by way of explaining fake monikers the first time around, “I always thought I was shielding you.”

“From what?” Zach asked.

“From the cruelty of the world,” she said. “I think that’s something that I took from being a father. Being the dad, I always felt that I was the shield, and now I’m the trouble.”

“I totally get it,” Zach replied. “But no one’s ever given me a hard time.” 

Zach even talked about his family on national TV this week, telling Brian Williams in an interview set to air Friday night, “If normal is a family that has a mom and a dad, and two kids and a white picket fence, then no, I don’t live in a normal family. But if a normal family is one where everybody treats each other as a family, and as equals, and with love, then yeah, I live in a normal family.”

Getting honest stories about trans people and their families into the public eye is one of the main reasons Boylan—who appeared on The Today Show Friday morning, has been on Oprah several times, and takes on frequent speaking engagements—continues to put herself out there.

“When I was a Wesleyan University student in the late ’70s, I knew I was trans, I tried to learn about other people like me, and there was nobody. Who? Renée Richards? I couldn’t relate to her at all,” she explains, referring to the professional tennis player who underwent sex-reassignment surgery in 1975. “Sometimes I wish I had my privacy back, but on the other hand, now, whoever the equivalent of me is at Wesleyan knows that I’m in the world. They know that Chaz Bono’s in the world. They know there are all sorts of ways of being trans. And that’s good work to do.”

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