At 42, James Boylan was married to a woman he loved. They lived in Waterville, Maine with their two sons. Boylan taught English at Colby College.

Then he became Jenny. Never at home in a male body, Boylan underwent gender reassignment surgery and wrote about it in her 2003 memoir She’s Not There: A Life in Two Genders. Her new book, Stuck in the Middle with You: A Memoir of Parenting in Three Genders, reflects on what her transition to a woman means as both a parent and a partner in her family, which has remained united. We spoke about what she’s learned about women, how she and her wife Deedie navigate intimacy, and what her experience tells us about the ever-changing concept of the American family.

Can you talk about the transgender spectrum?

Transgender is a way of talking about all sorts of gender-variants as if we had something in common with each other. Gender-queer people, cross-dressers, transsexuals, and drag queens don’t really have all that much in common. Ru Paul who, when the wig is off, is a gay man, doesn’t have anything in common with Amanda Simpson, who was appointed in the U.S. Commerce Department by Obama as the first transgender presidential appointee. They might not have anything in common with someone like, say, Leslie Feinberg or Kate Bornstein, who are more interested in the political aspect. They are very different.

Is being transsexual genetic? Is there a biological component?

The science is getting better, but it’s not especially conclusive. Trans-sexuality seems to have its genesis in the sixth week of pregnancy when fetuses form brain structures usually associated with that of the opposite sex. It might have to do with the hormone bath that the fetus is in or it might be something else entirely. I don’t know if it’s genetic, but it does seem to be neurological. It’s not related to anything you grow up with. It doesn’t have to do with how your parents treated you. And it doesn’t have anything to do with whom you’re attracted to. Although sexuality and gender overlap in such interesting ways that it’s easy to get confused.

What are the biggest misconceptions people have about transsexuals?

The hardest thing is for people who aren’t transsexual to be compassionate and have the imagination to recognize that this is the defining crisis of someone’s life. If you’re trying to live in a body that you’re not wired for, it’s like paddling upstream against the current in a tiny boat. Because people who are not transsexual have never had this problem, they assume that it must not really be a problem. If you’re not trans, you wake up in the morning and don’t worry what sex you are. For people who do have to worry, people for whom it is a constant, agonizing heartbreak, others think it’s funny or strange. It’s a measure of our compassion as human beings. Can you understand the problems of someone who is not you? I didn’t change genders because I was really gay and couldn’t accept it. I didn’t change genders to be more feminine, quite frankly. It’s not about femininity, it’s about femaleness. It’s not about playing with dolls or making brownies or whatever cliché of femininity we have. It’s about finding peace in your own skin.

How has the media played a role in shaping the way the public responds to transsexuals?

I was on the Larry King Show in 2005 and remember having a conversation about the caption below my name saying “professor” or “author.” They ended up using “had sex change operation.” I thought, really?

Why aren’t there many role models for transsexuals?

Gay people who are out increasingly spend much of the rest of their lives going about their business. Transsexual people, if they come out in a public way, more often than not fade into the woodwork in two or three years. A lot of trans people “go stealth” which means that you transition and move somewhere and don’t tell people about your past. But if sexual transition is marked by seamlessly integrating into the culture, there aren’t visible transsexual people of an older generation. If you think of trans people you know, it’s mostly people on the street who don’t pass well. But if a transsexual does pass, you don’t know.

When transsexuals go through transition, the great question is: Who am I going to be on the other side? Will I be some completely new person? The great surprise is no, of course you’re not. I went through the adolescent period that transsexuals go through, feeling out what parts of the new personality were going to be the keepers. There are probably some things that are a little different, but I’m not conscious of them. You still have the same history, sense of humor, parents, and children as you had before. What I don’t have is secrets. It’s not so much going from male to female as going from a person who had secrets to a person who doesn’t have secrets anymore. The big thing is, I wake up in the morning and don’t have to think about gender.

When Deedie gave birth to your boys, did you re-question your sexual identity? Or did you think, “Ok, I’m a father now”?

Yeah, I felt, I’m a father. Any ambivalence about being a man I have to let go of because it’s now about something bigger than me. When they were born I thought, “Okay cowboy, you better get in character here!” And I’ll tell you what: If I could’ve pulled off that stunt, I would have. But I wonder if I could’ve given them a better life. I think maybe all of our lives are better, full of more surprise and gratitude as a result of having to find our way through this domain.

When you first came out, did men and women react differently?

Absolutely. Women, generally, were very welcoming. Almost from the get-go, women were like, “Welcome to the sisterhood!” One friend from Ireland wrote, “Welcome! It’s bloody brilliant being a girl.” But even the hippie, groovy boys I knew from college were very uncomfortable. Some of those relationships have never really been repaired. There was much more negotiation that had to be done. And some of them may never have quite accepted me as a woman but kind of play along with me, which I find insulting. The women were interested in the transition and wanted to talk about womanhood and gender. And maybe women are more accustomed to knowing that gender is a difficult world that has to be navigated whereas the guys didn’t want to hear about. It might also be that a lot of my close male friends were upset that I’d kept something hidden. You can see how they’d respond with disbelief and a sense of sadness that they didn’t know me in the way they thought they did. So it could’ve been a sense of loss.

What did you learn from your father about how to be a man? And how have you passed that on to your boys?

The things my father taught me are very different from what I’m teaching my boys. A lot of them have to do with silence and being strong for other people and not being particularly emotional. I think my sons are more emotional and more loving as a result of having both Deedie and me as parents.

He died before you came out—how do you think he would’ve reacted?

He wouldn’t have liked it one bit. He belonged to a certain class of men who, if you have a problem, you keep it to yourself. If someone in the family has a divorce, it’s a shame we don’t speak of.

What have you learned about women since you’ve become one?

No one goes from male to female in this culture in order to get a better deal. I immediately noticed downsides—both in terms of little things like not being listened to in the same way, being less of an authority figure in the classroom than I used to me, to feeling vulnerable. I used to be fearless, I would go anywhere. And I’ve felt threatened by men, especially when I was out with the band, playing at sketchy bars late at night. So I feel more vulnerable in the world. But guess what? All of these problems belong to me. They come with the territory. I won’t make light of any of them, but they’re a fair price to pay for being yourself.

What about the positives?

I cry freely and I laugh freely. I don’t hesitate to express love for people, and I live in a much more emotionally volatile place now. Ninety percent of the time, it’s a really good thing.

When you were a father, you were “goofy, feckless”—and now, as their mother, you nag more. Can you talk about the shift?

I wonder whether, to some degree, it’s cultural. Whether men have more room to play in. I’m still the goofier of the two parents. But changing genders is a harrowing experience. It left me sobered up in the world. And the older my sons have gotten, the more dangerous the world seems. When they were little, I could protect them by feeding them and holding them. But when they get in an automobile and drive away, there’s nothing I can do to save them. In some ways, it’s not only gender—it’s also the passage of time.

How have you and Deedie negotiated co-parenting?

We had a pretty egalitarian marriage even back in the day. Early in the transition, we were on new ground. We’d both be in the ladies room at the same time—that was weird. Or there’d be two women’s blouses in the hamper. But we both cook, both nurture the boys. Deedie was a soccer coach for years. So we were never socked in traditional gender roles. I think that’s true of a lot of couples. What it means to be a husband or wife has changed.

The gender of the parents means nothing compared to the love that they bring to each other and to the kids

You say that part of being a man is “to be silent.” Has becoming a woman allowed you to be more open?

Yes. My job as a dad, I felt, was protector. Sometimes you keep your family out of trouble by keeping your mouth shut. A lot of women would disagree, but a lot of men would probably say, “Well yeah.” I thought I was protecting my family by not being public about being trans. I carried a lot of sadness around, but thought I was taking the bullet for my family. I’ll bear the sadness if it keeps us from having a really weird life. I think our family is more vulnerable now. But we’ve been mostly really blessed. We’ve seen how good people can be. Many people I expected to lose when I came out stood by me. I married Deedie because I thought love would “cure” me. And I was cured by love—just not the way I thought. Finally someone loved me enough to stand by me when I went through this.

Your title states that this book is about life in “three genders”—what’s the third?

That’s the in-between period I visited in the heart of transition, when people perceived me as male or female based on random cues, like whether I had earrings in, or whether my hair was tied back. But you don’t have to be transgender to know that there’s plenty of room in the definitions of “maleness” and “femaleness” and if you think of gender as a wide spectrum, with Arnold Schwarzenegger at one end and Christina Hendricks at the other, well, most people don’t live in those extremes. Most people fall somewhere along the spectrum. That’s the great thing. It should be about living anywhere along that spectrum that feels like it’s you.

You write, “Every single family in the world is a nontraditional family.” How has the idea of a “traditional” American household evolved?

Increasingly, Americans seem to be able to incorporate all kinds of difference into their lives. There’s more acceptance of gay marriage, kids have friends whose parents are gay. Our culture has become more diverse and more accepting. I don’t want to sound like Pollyanna because I know how kids are bullied. And I just read about a transgendered woman in Ohio who was murdered. It’s a very tough world for transgendered people. But I do believe that things are slowly getting better.

What can your experience teach us about how children grow up in non-traditional households?

I’m not saying it doesn’t make any difference whether it’s a man and a woman, or two women, or a single parent. The differences in families affect how children develop. But the gender of the parents means nothing compared to the love that they bring to each other and to the kids.

You claim, “Motherhood and fatherhood are no longer unalterable binaries.” Do you think we are now at a turning point in history where roles are being rewritten?

As long as people keep loving each other, there will be families with two parents and some kids. As long as those people have different characters, they’re going to do different things as parents. It will be more a result of their character than the feeling that they have to be a certain way because they’re male or female. We’re seeing lots of dads staying home and being nurturers and a lot of women in the workforce. As long as there’s love in the family, the specifics of each person’s job doesn’t really matter, does it?

Growing up as a boy, did you desire men sexually?

No, never.

Did that happen as a result of your transition to a woman?

I would still define myself as a lesbian. A lot of the trans women I know, if they’re single, will check out men to see what that’s all about, but will often return to women, if they were attracted to women in the first place. There’s no generalization you can make about what people will do after transition. Post-transition I began to see men differently. I was able to see what was cute about men, what was great about them, to appreciate them with a sense of love and gratitude. I don’t know if that’s quite been the same as lust. My polestar has always been Deedie and my sense of desire has never been very far from her.

Did your desire for her change when you changed genders?

It did. Orgasm as a woman is very different, and sex drive is different. All those things are true. But the object of all that desire for me, very specifically meaning Deedie, hasn’t changed.

There’s a heartbreaking moment in your book when the ball drops on New Year’s Eve and Deedie won’t kiss you. How have you negotiated the loss of sexual intimacy in your relationship?

I don’t want to be glib about this serious issue because there are times when not having a more vigorous intimate relationship drives me crazy. It’s an issue we wrestle with. But all the love and the time we spend together and the family more than makes up for that. I don’t spend a lot of time staring out the window wiping the tears away. I think that, in some ways, the relationship Deedie and I have might be more familiar to people who have been married for 25 or more years than you might think. When we first went through transition we weren’t sure if we could get through it, but now it doesn’t seem particularly hard.

Is there any part of being a woman that you think you’ve missed out on?

There are some things I’m never going to learn. Like a French braid. I’m never going to know how to do that. Screw that. You know what’s funny—hormones had such a dramatic effect on me early on. My first four or five years in the female sex I had a period of looking like an attractive young woman. That was really cool. But my body has caught up with its chronological age. To some degree, I’m sorry I missed out on some of the party of being in this body when I was young. But it’s beyond silly to look behind your shoulder and wish things could’ve been otherwise. My life as a boy was not a bad life. I was really a very lucky person. I’d published novels, I fell in love, I had children, I got a teaching job in Maine that I love. And then I went through the transition and I’ve had this life. It’s pretty hard not to be grateful. I’ve seen things that most men and most women have never gotten to see. The thing that I thought used to be the great curse turned out to be a gift.

Your community has been, for the most part, incredibly supportive of your transition. If you lived in a different part of the country would this have been a harder experience?

I think it would’ve. I think some people don’t think I’m aware of exactly how lucky I’ve been, and I can tell you—I am aware. It does have something to do with living in Maine, where people respect your privacy a little bit. It has a lot to do with race and social class and education. But it’s also sheer luck. Nothing bad has ever happened to my children, and very few bad things have ever happened to me.

It’s interesting when you point out that a lot of your friends have divorced while you and Deedie have stayed together.

What has brought Deedie and me together is not my being a woman but us going through something that was very hard and having to rely on each other. The loss of her sister and then the loss of my own mom were harrowing and sad. Those moments teach you the depth of your relationship, the depth of your love with someone. When we first started going through transition, people said—”Oh, you need to divorce, you need to marry men.” The idea that the two of us would choose each other didn’t occur to them. And as the people who told us to get a divorce have themselves gotten divorced, we think people should be careful about the advice they give. One thing people said was “oh those poor children”—and now I’ve got a freshman at Vassar and an 11^th grader who was just inducted into the National Honor Society, who was singing and dancing on a stage last week, who builds beautiful origami, who’s a nationally ranked fencer. Both of my boys are delightfully funny, smart kids. When people say “What about your boys” I want to say, “What about your boys?”

You interviewed authors about their experiences as parents and children. What did you learn?

The experience of being a child exists on such a wide, wide spectrum. You look at Edward Albee whose resentment of his adoptive parents still simmers. He’s still angry at these people for not understanding him. Rick Russo whose father wasn’t around at all, always going to the track or two the bar, loves his father and forgives him. There are so many different experiences of childhood and parenting that it’s remarkable we’re talking about the same thing. We should be grateful for all of it and spend less time worrying where we fit in.

This interview is edited for length and clarity.