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Jennifer Finney Boylan © 2007 Photo by James Bowdoin

Wit and wisdom

“You’ve gone to a lot of trouble to become a woman — don’t be a stupid one”

By Keith Garsee on November 18, 2015

Jennifer Finney Boylan, author and activist, is the Anna Quindlen Writer in Residence at Barnard College of Columbia University and the special advisor to the president of Colby College in Waterville, Maine. She also serves as the national co-chair of the Board of Directors of GLAAD, the media advocacy group for LGBT people, and sits on the Board of Trustees of the Kinsey Institute for Research on Sex, Gender, and Reproduction.

Her 2003 memoir, She’s Not There: a Life in Two Genders was the first bestselling work by a transgender American. Last July, the 57-year-old parent of two sons became a regular cast member on I Am Cait, the hit docu-series about Caitlyn Jenner that was just renewed for a second season. She has an ever rising social media presence (11,200 followers on Twitter alone) and recently joined comedy writer Keith Garsee at The Hungarian Pastry Shop on New York’s Upper West Side to discuss life as a transgender icon, her new book and her star turn on I Am Cait.

NEW YORK, NY - MAY 09: Author Jennifer Finney Boylan (L) and psychotherapist Deirdre Boylan attend the VIP Red Carpet Suite hosted by Ketel One Vodka at the 26th Annual GLAAD Media Awards in New York on May 9, 2015 in New York City. (Photo by Brad Barket/Getty Images for Ketel One)
Jennifer Finney Boylan (L) and her wife, psychotherapist Deirdre Boylan, at the 26th Annual GLAAD Media Awards in New York on May 9, 2015. (Brad Barket/Getty Images)


Women in the World: Before we met, I Googled “things you’re not to say to a transgender person,” and your interview with the Huffington Post turned up at the top of my search. In it you advised people to keep it simple. You said, “Why not just ask a transgender person ‘How are you?’” So, how are you?

Jennifer Finney Boylan: I’m fantastic! Thanks. The reason I said that is because when people meet someone who is transgender they tend to look at that person through one lens. But you know, if you’re transgender, you don’t want to be defined by that, anymore than you’d walk up to Barack Obama and say “so what’s it like being a black guy?” It’s not the first thing you would ask the leader of the free world.

WITW: It might be the first thing I would ask.

JFB: Yeah ok, but other than you. [Laughs] So, um, I guess we can dive right into the question of identity with this because, am I really still a transgender woman? I mean, I went through the transition twelve years ago, so in many ways all the dust has settled in my life . Now I simply identify as a woman. I didn’t go through all of this to become a woman with an asterisk. At the same time my history is different from that of many other women, and it’s something that I’m proud to talk about. The reason I suggested that people not immediately dive into all the trans stuff is because you don’t want to identify transpeople with just this singularity of the life when what you have other things in common with them that might be both more interesting and more important.

WITW: How did you start your day today?

JFB: I just moved from Maine into a new apartment here on Riverside Drive. I lived here, in this very neighborhood, and had coffee in this very pastry shop from 1980 to 1985, before I transitioned.

WITW: Does this feel like a homecoming in a way?

JFB: Um, no it feels more like going back to your old high school and they’ve torn down all the buildings and you don’t recognize anybody. New York has changed so much in the past thirty five years. When I lived here on 108th and Amsterdam, my roommate was a young man named Charlie Kaufman…

WITW: That name sounds familiar.

JFB: …who has since become an Oscar winning director and screenwriter of Being John Malkovich and Adaptation and The Eternal Sunshine of the Spotless Mind and all sorts of really cool movies, but at the time he and I were roommates. There are all these stories of roommates. Like Wally Cox and Marlon Brando. Or uh, Tony Curtis and… oh, I can’t remember!

WITW: Probably Tony Curtis and Tony Curtis.

JFB: Ha! Right!? So we both lived here and we were goofballs and we had nothing, and he worked on scripts in his back room and I was trying to write novels in the front. I had moved here because it was my sense that moving to New York was what you did if you were a young writer, but I found it very difficult to write because I was also a young transgender-person at the time. But I was not out, not by a million years. It was a problem. How do you write about the world if you don’t really live in it? How do you tell a story if your own life isn’t true? In a weird way my secret really messed up my prose, a struggle that continued until I wrote She’s Not There. I had written other things before that but then, but they didn’t connect.

WITW: Was it the authenticity of She’s Not There that propelled it to such success?

JFB: Well if you spend three hundred pages with somebody you begin to have an intimate relationship with them, and readers can smell a rat. They can tell when information is being withheld. And I think my readers felt that in my early novels, which I published under my old name, James. I was an entertaining, kind of funny, sweet writer but I was always on the run from the reader a little bit. My work was missing an emotional center. So here’s a clever phrase: “When I changed genders, I also changed

WITW: Wow. That’s catchy!

JFB: [Laughs] I’m sure there is a doctoral thesis in there for somebody, but when I went from male to female I also went from writing fiction to writing non-fiction because in some ways both my life and the stories I wanted to tell about it became more truthful.

James Boylan at Vent Haven, the museum for retired ventrioloquists’ dummies, 1982. © Peter Frumkin

WITW: What quality most defines you as a woman?

JFB: Probably being a mother to my two now college-age boys. In some ways that’s a trick question. It begs an answer to ‘what do we mean by womanhood?’ That’s the thing about trans-stuff: a simple question like “how are you?” can plunge you into a very complicated discussion. For example, if you’re talking about transgender issues, you may be talking about transition. And if you are talking about transition you may be talking about medical issues. And if you’re talking about medical issues you’re talking about economics and money, and if you’re talking about economics in America, you’re talking about privilege and race. I wrote a New York Times op-ed recently in which I pointed out that the experience of transgender people is so different for rich people and poor people that its hard to compare the two. The truth is, if you put five transgender people in a room and asked them what issue was most important to them, you’d likely get five different answers. I like to say “if you’ve met one transgender person, you’ve met one transgender person.”

WITW: Is that also your own maxim?

JFB: It’s mine! For instance, one person might say “well being trans it’s like a medical condition, like a cleft palate. It’s about a trip to the doctor.” Another would say “it’s about queerness and subverting the normative certainties of the culture.” Still another might say, “it’s about political theory, it’s about seeing gender through the lens of cultural studies and thoughts.” A fourth might say “It’s about a party. It’s about being fabulous and having fun and bring your feather boa, and your fishnets!” In fact if you speak to someone from the drag community…

WITW: That last one seems to me like a drag community issue…

JFB: …well, but they’re under the umbrella too, supposedly. Anyway I could name a hundred people in each of those categories, and if you got all of those people together, they would have a great big fight. In fact, trans-people fight with each other all the time.
So if me and Caitlyn Jenner and Kate Bornstein, and [filmmaker] Susan Stryker all got in to a room together, we’re gonna disagree.

WITW: And you’ve been in that room.

JFB: I’ve been in that room! And one of the biggest problems for our movement right now is that we’re so mean to each other.

WITW: Mean as in…?

JFB: Mean. No one hates Caitlyn Jenner more than transgender people.

Caitlyn Jenner with Jennifer Finney Boylan. © 2012 Jennifer Finney Boylan
Caitlyn Jenner with Jennifer Finney Boylan. © 2012 Jennifer Finney Boylan

WITW: Why?

JFB: Well, people resent her privilege, people resent the fact that she is a white woman. A lot of these sentiments are expressed online, so I don’t know how deep it goes. But the most bitter critiques of her are from other transgender people who feel that she’s made the culture view us in one way — with perfect hair and makeup and fingernail polish. Personally I am a big fan of Caitlyn’s. I think she’s using her fame for good — she’s genuinely interested in changing the world for better. But there are many different ways to be trans…

WITW: And many ways to define your place in the world. 

JFB: Yes. A big problem for our community right now is that we don’t agree on the discourse. I think we must get to a place where we can accept that all forms of being trans are cool and that everybody has the right to be themselves. As we move forward and more trans people become known that will happen. Right now the movement is in its very early stages. But Caitlyn Jenner’s impact has been powerful.

WITW: Last month you were presented with the GLAD (Gay and Lesbian Advocates and Defenders) Spirit of Justice Award. What does that sort of recognition feel like for you?

JFB: It feels crazy, man. When I was twenty-two and living in this very neighborhood, I doubted that I would ever be able to survive. I didn’t think that I would live to be thirty. The idea of being able to walk down Amsterdam Avenue with my head held high and to “live my truth” was inconceivable, even though I was already hoping to go through transition at the time. I started seeing a psychologist right when I moved to New York in 1981.

WITW: Was that helpful for you?

JFB: No. It was terrible.

WITW: Why?

JFB: Because he was an idiot, and he didn’t know anything about trans stuff. For a long time, transgender people have known much more about their condition than the supposed experts that they go to. He told me things about myself that were not true.

WITW: Is he still practicing?

JFB: I don’t know. Screw him! What’s the Hippocratic Oath? “Do No Harm.” Well, that guy did a lot of harm to me.

WITW: Are you angry with that doctor in particular, or with the larger medical community?

JFB: Actually, I don’t harbor much anger towards anyone anymore. But turning for help as a young person is a really scary thing to do. It forces you to to confront the fact that you are not who you want to be. So when the one person you turn to for help tells you things that aren’t true…

WITW: Did you know at the time that they weren’t true?

JFB: Even then, I knew that what he was saying didn’t sound right. He thought I might be schizophrenic, or he said maybe I was jealous of my sister. He was a Freudian, he was convinced that I wanted my sister’s life or my mother’s life or something like that. But when you are young, you trust in the experts and so you say “oh I never knew that about myself!”

But I really wanted to say ‘No, I don’t want my sisters life, I want my life!” But in 1981 the psychological community was not paying attention. I remember taking a course as a sophomore at Wesleyan, and the only time people like me were mentioned was when the professor was discussing “Abnormal Psychology.” And I remember thinking, “Really? That’s all you’ve got? I don’t feel like a bad person!”

WITW: Did that class made you feel like you were a bad person?

JFB: It made me feel abnormal! And it gave me the sense that I was the only person on Earth — or one of ten doomed people on Earth — when I was actually part of a community of hundreds of thousands of relatively well-adjusted, good people.

Jennifer Finney Boylan on stage at the 26th Annual GLAAD Media Awards In New York on May 9, 2015. (Mike Coppola/Getty Images for GLAAD)

WITW: So all the kudos you are now getting must seem a bit strange.

JFB: For the longest time I thought I would be an embarrassment to everybody, or a disappointment, and instead…when I received my GLAD award I didn’t realize there would be a thousand people there. I probably would have worked on the speech harder! [Laughs] I have to say there are lot of people who probably deserve that award more than me. So I’m grateful, but I would have done the work even if I never got an award.

WITW: Are there times when you feel yourself thinking more like James than like Jennifer?

JFB: What does that mean? If you’re implying that there’s a different mindset…

WITW: Well let me finish the question. Are there real differences in the way that men and women perceive the world? Are there certain thoughts, behaviors or attitudes that you personally define as being more male or female?

JFB: Well, we really have to be carful with that statement, because it’s just one step away from saying that men and women are only allowed to do and think certain things. But it’s a great question for me. Growing up, before I transitioned, I often wondered who I’d turn out to be. I thought of myself as female, but I never had the experience of being female in the world, so I didn’t know would it mean to walk down the street or to go to a concert. Would that experience be fundamentally different as a woman than it was as a man? The first year or two after transitioning, everything seemed brand new. I’d go pump some gas, and I’d think “this is the first time I’m pumping gas, you know, wearing heels, wow!”

WITW: Pumping gas, wearing pumps!

JFB: Here I am at 7/11 having a Slurpee as a woman, how different this feels! But you know, a Slurpee is a Slurpee no matter what you are wearing.

WITW: What was the biggest change?

JFB: I think the biggest change for me was not going from male to female, but going from a person with a secret to a person who doesn’t have a secret. Keeping a secret has a profound effect on your life. It’s kind of like keeping a pet. A big, invisible pet. You have to take care of it! You have to tend to it! So, I’m free of that. But women are definitely treated differently in the world and early on in the transition I became aware of how during department meetings, for example, as a faculty member, I was suddenly not listened to, that men would kind of talk over me. Some of my students reacted to me in a different way. I lost some of my authority in the eyes of students. For instance, I would give a lecture in class as a man and students would write down everything I’d say. Now I give the same lecture as a woman and people are not taking notes quite so furiously. But the biggest change is feeling vulnerable in the world as a potential victim of assault.

WITW: Do you have a sense that you might be attacked at some point?

JFB: I did when I was younger. I used to get more harassment on the street, especially in New York, the classic construction workers whistling. But now it’s more like, if I’m walking home alone at night, and there’s no one around, I’m scared, in a way that I was not scared when I was a guy. And that’s a big difference. Unfortunately, it comes with the territory.

WITW: What other differences have you noticed?

JFB: After I transitioned I had a hard time connecting who I was to who I had been. I struggled for a little while thinking “What does it mean to be a woman if what you had looks to everyone else like a boyhood?” It was a strange boyhood, since I knew who I was in my heart, but no one else knew that, so I was treated differently from other girls, you know? So how do I connect who I am now to the person I had been? Everybody struggles over time to connect the past with the present, but that struggle takes a unique twist if you are trans.

You look in the mirror at age 57, as I am now, and you wonder “Where is that child that I was? Where is that teenager? You know, I was in my thirties when I transitioned. I’m much older now. So you have to confront a before-and-after not just in terms in terms of going from male to female, but also from growing from a younger woman into a middle-aged woman. We all struggle to connect our various selves, but how do we do that? My answer is we do it through the telling of our stories. We find the narrative of our lives.

WITW: And you figure out that narrative with time and perspective.

JFB: Yeah. What you want to do is avoid living a life where there is a before and after. Unfortunately, the world is full of formers and exes.

WITW: Well, for most people, life has a beginning, a middle and an end.

JFB: Yeah. But there are people who define themselves as a former marine, or talk incessantly about their ex-husbands as if the only way they can define themselves is in terms of who they had been. That seems unjust and unfair to the people they have become. I still am that scared ten year old, I am that 20-year-old we were talking about. All the people I have been live inside of me. But it’s important for us to live one life, and not two. And that’s true not just for transgender people but for everybody.

WITW: Does a television show like I am Cait increase acceptance of trans people?

JFB: It certainly increases visibility. You can criticize that show in all sorts of ways for what it is for what it’s not. You can criticize Caitlyn Jenner for who she is or who she’s not. But Cait is far from a typical transgender person. She’s really sui generis. We’re not going to have another Caitlyn Jenner, who was an Olympic gold medal winner and then was a part of the Kardashian family. Her celebrity has helped. The morning after she came out, everyone in America knew someone who was trans, and that’s wasn’t true before. But I think many transgender activists are a little exhausted by the whole thing, because we’ve been saying this stuff for twenty years, and suddenly everybody is paying attention because a member of the Kardashian family says it? Seriously? You know, I wrote a best-selling book, I’ve been on Oprah five times, I’m not exactly anonymous. There are others like Chaz Bono who have also done a lot of heavy lifting. So the fact that people are thinking about these issues for the first time because one of the Kardashians is trans is a little frustrating. And yet here we are now, because of Cait.

WITW: Has Jenner’s celebrity created a bandwagon effect? Are people jumping on this issue just because she’s famous?

JFB: I don’t really know. But transgender people seem to be the flavor of the month at the moment. Caitlyn just won the Arthur Ashe award. She’s Glamour Magazine’s Woman of the Year. And I think there are many transgender women who rightfully say “Well I came out 20 ago and I’ve been struggling with this cause for decades and nobody gave me an award and nobody gave me a show! What I got instead was a divorce and a sundering of my family and being fired from my job.” And that’s understandable. All that said, Cait is such a good soul. She’s really genuinely committed to using her fame to change the world and I think her transition was going to be headline news no matter what she did.

JFB and cast boy george
Singer Boy George (third from left) with ‘I Am Cait’ cast members (L-R) Jen Richards, Jennifer Finney Boylan, Caitlyn Jenner, Drian Juarez, Candis Cayne and Chandi Moore. (Facebook/Jennifer Finney Boylan)

WITW: You think she’s making a real impact?

JFB: Well, maybe. Hopefully. You’re talking about the most maligned and disrespected minority group in the country — people with higher rates of homelessness and violence and harassment than any group you can name. So how can I object to people celebrating us for once? What I fear is that eventually all of the excitement will die out, and people will go on to something else. We are a long way from full equality in the world. If it takes a celebrity to get us there, fine. With a little more visibility maybe we’ll all go to a good place.

WITW: And now you’ve become a celebrity yourself.

JFB: Do you really think that’s true?

WITW: I do! You have a huge social media presence.

JFB: It’s funny to me, because it’s never felt quite real to me. I feel like Rhoda Morgenstern to Kate Jenner’s Mary Tyler Moore.


JFB: I’m so glad you know who that is. Because I said that to somebody the other day and they said “Rhoda who?”

WITW: Well I don’t think you’re second fiddle to anybody.

JFB: My proudest moment on the show was when I sat down with Cait one day over lunch, and I asked, “What’s up with you, are you going to date again? And she’s like ” I don’t know.” So I asked her, “Well, are you attracted to men or to women? It’s clear to me that she’s attracted to women but she won’t say it because I think she still has some internalized homophobia. She won’t say “I’m a lesbian!” She just won’t say it! Instead she says, “Well, if I went out with a man it would make me feel more like a woman.” And I thought “what the hell does that mean?

I mean, seriously, you don’t need a man to make you feel like a woman, you are a woman right now.” So I said to her “You’ve gone to a lot of trouble to become a woman, don’t be a stupid one.” [Laughs] The role that they have me playing is the so-called “voice of reason,” which is nice, I guess. I mean, I’m never going to be more glamorous than Candis Cayne. I’m never going to be the star of the show.

In New York, 2006. © 2012 Jennifer Finney Boylan.

WITW: I feel like in a way you are more glamorous than Candis Cayne.

JFB: [Laughs] Well that’s why you’re my new best friend! Candis is … God, I love her! I love all the women on the show, I have to say. But Candis was the breakout star of season one because there is a sweetness to her and she is fabulously beautiful. People love her. So for me, you know, I’m never going to be the glamor-puss. I’m one of the few lesbian identified women on the show, and I’ve been with the same partner for years. I’m also the only person who is married and has a family, except for Caitlyn, so in some ways I’m kind of like the elder statesman, or stateswoman. I’m the voice of stability. It’s nice but there’s a little voice in me that’s like “Seriously, can’t I be the glamor-puss just once? Maybe if Candis is sick one day?”

WITW: Tonight, on a very special episode of  I Am Cait

JFB: Yeah! In fact, Candis showed us how to flip your hair around.

WITW: I’ve noticed that you’re doing a lot of hair flipping.

JFB: [Laughs] I did this show for three reasons. One, because I thought it would be fun, and it is. Two, I thought it would help raise visibility and help us move more towards equality for trans-people, and it’s done that. But the third and most personal reason was that I hoped it would shine a light on me as a writer, and God forbid, help me sell some books. In fact, everything I have ever done in the media is ultimately about trying to sustain my career as an author because, as you know, being a writer in this culture is near impossible. So the ironic thing is that I’ve now got all these fans and followers who have no idea I’ve ever written a book.

WITW: Do you think the transgender trendiness we’ve seen over the past few months will be short lived or does it signal a cultural shift?

JFB: It’s definitely a shift. And it’s really funny, if you talk to people under 20, or under 25, in many parts of the country, trans-issues are just one more thing. My son brought a friend home for Thanksgiving last year, and he’d been around for a day or two before I realized he was a young trans man. I said to my son Zach “you didn’t mention that your friend was trans!” and Zach said “Oh yeah, I didn’t think it was that important.” Certainly on college campuses now you see a lot of trans people, and more gender-queer and gender non-conforming people, which may mean in the future there will be more of those folks going about the business of living their lives in the world. It’s funny, because I’m not exactly the transgender superhero they are looking for. Some activists be look at me and see a person who appears kind of binary.

WITW: And what is binary?

JFB: For transgender people binary means that there was a time when people thought you were male and then you went through the transition and now you identify a female. It’s a full transition that involves things like hormones and a trip to the doctor’s office. Younger people I see on college campuses and elsewhere seem to be more in the middle. People who are maybe gender fluid, or who identify neither as male nor female. So the idea of going from one end of the spectrum to the other…there will be fewer people like me around in the next generation, which is fine. Again, what I’m hoping is that are many different kinds of trans-people in the world and there is no one right way to do it.

Boylan family, fall 2007. © 2012 Jennifer Finney Boylan.

WITW: When you go out, are you constantly aware of people’s reactions to you? I think that would drive me crazy.

JFB: People are very rarely rude to me in my presence. If people have reservations about me or about transgender people in general, I hope that in time they will change. What people think of me today is not necessarily what they will think tomorrow or next year. It can take a long time to get your head around this, and you know how I know that? It took me a long time to get my head around it. It took me half a lifetime to accept myself. I don’t have another half a lifetime to wait around for other people to catch up, but I try to be patient. What can you do accept treat people with love and hope that other people will treat you with love?

WITW: We’re increasingly seeing people undergo gender reassignment at younger and younger ages. Is that a positive thing? Are some people too young to know how they really feel?

JFB: I think the media has really focused on this question because the idea of child mistakenly changing genders is kind of like the stuff of a horror movie. But my experience is that young people coming out with a certainty about who they are and who they are meant to be are generally to be trusted. The protocol now is not to have surgery when you’re six years old. Instead the protocol is enabling young people to be who they want to be and accepting their decisions. So that means they can grow their hair as long or as short as they want it to be. If they want to change their name, they can change their name. If they choose to wear a dress — or not wear a dress — that’s fine. None of that is permanent. We’re teaching these kids that there is nothing wrong with the way they feel, and that who they are is a gift from God. Being a human being is never simple — even when you’re 10. It’s too early to conclusively say if surgery on younger people is good or bad. But if all we’re doing is treating them with love in response to their desire to express themselves, how can that be wrong? When kids get to be a little older, sometimes doctors prescribe so-called puberty blockers, hormone blockers, so that if you identify as female, you won’t experience the effects on testosterone on your developing body.

WITW: Is this a new thing?

JFB: No, it’s been around for a while. Hormone blockers can delay the moment of final decision for years and years and years. So again, there’s a road back if someone changes their mind, but in my experience, most people don’t change their mind. Over the last twelve years I have met about 15,000 transgender people, and during that time I’ve met maybe half a dozen who regretted the transition.

WITW: What do they do about that?

JFB: Well some of them de-transition, and go back. And some of them go back not because they don’t want to change but because full transition means losing their family or their job. It’s not that they don’t want to go through transition, it’s because they don’t think they can survive.

This is a really hard life to live. It’s getting easier, but it’s still really hard. For some people it can seem almost impossible. If someone decides to embark upon this life, you can be sure that they are really confident of their decision. Even people I know whose lives have been really hard — people who’ve lost their families and jobs and are holding on by their fingernails — even those people don’t regret their transition for a minute. They say, “well this was the price I had to pay to live an authentic life.”

WITW: What kind of role do you play in the transgender movement?

JFB: I’m the scribe. Sometimes I think I’m the jester [laughs]. It’s not a role I signed up for somewhere. There are dozens and dozens of memoirs and books written by transgender people. But — I’m trying to think of a way to say this in a modest way, and there’s really not a modest way — but I believe in my heart, that the transgender tipping point we’re in now began with the 2003 publication of  She’s Not There and my appearance on Oprah when it was published. It was the first book authored by somebody who was trained as a writer. Soon after I got involved with GLAAD and have served as co-chair for three years, because before me no transgender person had lasted here for more than a year. I stayed and helped hire the new CEO. And I also put transgender issues on the agenda. We now spend more than a million dollars a year doing transgender advocacy work.

WITW: What is the relationship between transgender activism and feminism?

JFB: In the early 70s there was real antagonism between the two. A whole generation of feminists just didn’t get it. And some of them are still kicking around, so called TERFS (Trans Exclusive Radical Feminists) who have a very essentialist view of womanhood that is fundamentally hostile to people who are born as trans.

WITW: Who are those people?

JFB: I don’t want to mention their names. They are a very small sect, but they get more attention than they should because they say ridiculously hateful things. But they’ve been left behind. In the ‘80s, feminism was reimagined through the lens of queer theory. The direction of feminism was changed by the experience of lesbians and bisexual people and gay men. Then, in the 2000’s queer-feminism was again reimagined again, this time through the lens of transgender people. So feminism keeps evolving. Elizabeth Cady Stanton and Susan B. Anthony might not have necessarily gotten along very well with Betty Friedan and Gloria Steinem. And Steinem might not have necessarily spoken the same language as Randi Shilts. The conversation keeps changing over time. But the great thing about scholarship is that as our body of knowledge expands, the field does as well. Feminism right now is quietly supportive. Even Gloria Steinem, who used to be quite critical of the transgender movement, recently came out and said “I was wrong.”

WITW: You have a new novel coming out soon.

JFB: I do. It’s called Long Black Veil. It’s a literary thriller.

WITW: Has your writing style changed since your very first book?

JFB: My very first book was a collection of short stories entitled Remind Me to Murder You Later, which is filled with one hundred percent authentic juvenilia. Long Black Veil is unlike anything else I’ve written. When I had my other by-line I think I was a much goofier writer. But the new book is a literary thriller, there’s a mystery at it’s heart. There’s a murder. There’s missing person. There’s an abandoned prison into which young people are accidentally locked. The novel starts with a group of friends, recently out of college, who break into an abandoned prison to look around and they get locked in. Then they find out they are not alone.

WITW: It sounds creepy!

JFB: It is creepy! That’s as much as I’ll say!

WITW: What’s frustrates you the most about the public discourse about transgender issues?

JFB: I’m always surprised that people don’t react to people’s troubles with more compassion. You don’t need to be Oliver Sacks to understand that neurology and biology interact in strange ways to make us who we are. I think the best reaction to someone else’s way of being human is curiosity and love. People will offer you their opinions: “Well, there’s no such thing as transgender people” or “I don’t believe that you can change sexes,” but their opinions are based on nothing. They are based on the fact that you yourself have never suffered from this particular condition. It’s based on the fact that you have never met anyone who is trans. It’s based on the fact that you are confronting something you don’t understand, but have nonetheless decided to have an opinion on. Understanding transgender issues requires you, to have a moral imagination and to understand what it must be like to experience the world in a way other than your own. Most people would rather not do that.

WITW: Who are the women you look up to?

JFB: I think Bonnie Raitt is pretty kick-ass, because she’s a woman who’s succeeded in a man’s world. Blue’s Rock and Roll is a very male world! She seems strong, she rocks, but she’s also not afraid to show her vulnerable side. I admire that. I also admire Donna Tartt and Jennifer Egan as writers. Jennifer Egan is the kind of the writer who I most wish I could be. She’s the most inventive writer of my generation.

WITW: What have you learned about yourself from your children?

JFB: Being a parent is tremendously important to me. I learned that my capacity for childish behavior is nearly inexhaustible. Sometimes when I’m in the presence of younger radical people who are angry with me for not being more radical, I want to say to them “You want to do something radical? Raise a family. A transgender parent raising two sons in a small town in Maine? If you don’t think that’s radical, then you’re just not paying attention.”

This interview has been edited and condensed.

E! has announced a second season of I Am Cait, to premiere in 2016. Jennifer Finney Boylan will again feature in the cast.