The Conversation with transgender icons Jennifer Finney Boylan and Kate Bornstein

AP, Santiago Felipe

Jennifer Finney Boylan, left, and Kate Bornstein

In this signature espnW column, Allison Glock sits down for a candid Q&A with remarkable people. The aim is to cover topics high and low, deep and less so, to present a fresh look at folks we think we know and meet some others we wish we'd known all along. Welcome to The Conversation.

Who: Transgender icons, best-selling authors and now reality TV stars from Caitlyn Jenner's "I am Cait," Jennifer Finney Boylan, 57, and Kate Bornstein, 68.

Where: Patsy's Pizza in Harlem, New York.

When: April 5.


Allison Glock: You've just wrapped "I Am Cait," where the two of you took a long bus tour with Caitlyn Jenner and made more impact and noise than anything she did or said. Your debate over the word "tranny" early in the season went viral.

Kate Bornstein: [Laughs] Oh yes.

AG: Kate, you feel the T-word is a "family" word, while Jenny, you see it as a slur.

Jennifer Boylan: When you watch the first couple of episodes, there was a lot of yelling on both sides, including me. There was a lot of people getting up and leaving rooms and closing doors. I believe I hit Caitlyn Jenner with a rolled up newspaper.

AG: But in pretty short order you and Kate were able to see each other's points of view and arrive at a place of mutual respect and civil disagreement, a rarity these days anywhere, never mind on reality TV.

KB: I've had a friend for over 40 years who is a card-carrying member of the Tea Party. What we have happening in this country now is that somehow it's OK to break off a friendship with someone if you find that their politics are counter to yours. I don't want to see you anymore, get out of my life. Or, I don't even want to try and get to know you because your politics are so divergent from mine. And then we get so angry with our politicians when they don't compromise. So, yeah, when it was time for Jenny and me to come to loggerheads and resolve that issue, I knew there was some dynamic in what we were doing that could be applied more widely.

JB: And we got better at it. Kate and I got the idea that if the other women could see us working it out, then the rest of us could do the same. Kate was brilliant coming up with a safe word -- which was "God Bless America" -- for talking about politics.

KB: Caitlyn insists she is only a fiscal conservative, but her fiscal conservatism is the kind that would brand helping fund shelters for homeless kids as an entitlement, so you don't need it.

JB: She'd call it "free stuff."

AG: So I'm guessing you said "God Bless America" a lot.

KB: [Laughs] That we are all trans makes the debate easier for people to watch. It's like, look! Trans, trans, trans! And the deeper stuff is taking place simultaneously.

AG: What surprised you the most on the show?

No matter who wins the White House in November we are still going to have a country where about half the people don't talk to the other half. How do we have a conversation with people with whom we disagree with respect and with love?
Jennifer Finney Boylan

KB: That I could get along with six trans women. I never have before, not really.

JB: Yeah, I'd say the same thing. Here's the irony. The most progressive, subversive, radical show on TV is a reality show on the E! Network with a Tea Party Republican as its star. And there's a lot of people who can't get their minds around that, but if you can live with contradiction you will hear some of the most amazing conversations that have ever been on TV.

AG: Critics of the show and of Caitlyn seem unwilling to overlook her worldview.

JB: So many people are unable to get their head around the fact that Caitlyn Jenner is neither their savior nor their enemy, but something in the middle. You can have a conversation between a Socialist and a Republican and it can be glorious. We should reject the binary not only in terms of who we are but also in terms of how we see the world. In my opinion, the show is not about Caitlyn Jenner and it's not about trans people. The show is really about: How do we talk to each other? The country is now full of people who disagree. And no matter who wins the White House in November we are still going to have a country where about half the people don't talk to the other half. How do we have a conversation with people with whom we disagree, with respect and love? And that's kind of what we figured out how to do. Not all the time.

AG: Was this something you did intentionally? Trojan horsing some sort of depth and relevance into the proceedings?

JB: No. Our job was to get Caitlyn out of her comfort zone, that's all we were told. I didn't like provoking her. I'm not naturally a person who seeks conflict. I'm not even all that good for standing up for myself in a fight. Given the choice, I would much rather run away.

KB: Jenny is a scholar.

JB: There was a little room in the back of the bus where you could sit and gaze out the window, and I was frequently back there, especially when people were carrying on in the front room, talking about lipstick. I'd be alone, reading Thomas Merton, "The Seven Story Mountain," which is this somber ...

KB: It's a Christian take on Buddhism, basically.

JB: It was an odd choice for the road. [Laughs] So, yeah, I'd be reading Thomas Merton and I would look up and the producer, Andrea, would be standing there with her hands on her hips. And I would say, "What?" And she would say, "Professor Boylan, did you know we're making a television show out here?" And I'd come out, and they'd say, "Now we want you to ask Cait about her sexuality," which of course I would never do in real life. I was constantly complaining. Everything was below my dignity. Of all the people on the show, I was the biggest pain in the ass.

AP Photo/Joel Page

Boylan at her home in Belgrade Lakes, Maine, in 2008

AG: Kate, is this true?

KB: No. Jenny is well loved. She is ... quirky.

[The waiter approaches asks if they want wine.]

KB: Not I, thank you. I don't drink, I do drugs.

JB: I'm not drinking right now. I gained like seven pounds during "I Am Cait." When I get lonely, I eat, because I love food.

Caitlyn believes her personal charm will solve almost any situation she is in. She really believes that if there are people who hate us, they just haven't met her yet.
Jennifer Finney Boylan

AG: You were lonely on the show?

KB: Well, she was away from her wife and family. And we would eat in four-star restaurants or greasy truck stops. And whenever we would get to a hotel for the night, they would have put out all these great snacks.

JB: And then room service. Like I'm really not going to have room service if someone else is paying for it? Are you kidding me? I'm not going to have a nice martini and a steak for dinner? Who lives that way? No one. But back to the show, you know, when I'd finally get in there with the other women, it would be great because we'd have the most interesting conversations I have ever had with other trans people and it's because we're all so different. Among the six of us, we have different ways of being trans, people from different socioeconomic backgrounds, people who are of different races, people for whom being a woman means different things, in some cases very different things. There's at least one person on that show who doesn't identify as a woman. There are different ways of occupying the LGBT space. You have a person who is 18 years old and you have a person who is 66 years old. That's a lot of ground.

AG: That was also evident in the most recent GLAAD Awards, where, Jenny, you are the current co-chair.

JB: When I first joined GLAAD six years ago, there were like five trans people in a room of more than a thousand. It was pathetic. And this year I think almost half of the shows and stories that were nominated were about trans people or starring trans people or covering trans issues. It was a new generation of queer people being celebrated. We raised a gazillion f---ing dollars, which keeps the lights on. So that made me feel really good. And I was seated next to [director] Lilly Wachowski, who was making her debut, her first public appearance [after announcing her transition]. I was supposed to sit next to her and hold her hand and tell her it was going to be OK. And then she got up and she gave a remarkable speech. Smart, intelligent. The last line was, "Now get out there and f---ing love somebody."

AG: And "I Am Cait" won an award for outstanding reality show.

JB: It tied with "I Am Jazz" [about 15-year-old transgender activist Jazz Jennings]. Caitlyn and Jazz standing side by side -- the alpha and the omega of the trans universe. Not that it's a binary, god forbid, but there's a lot of difference between where they are, and not just generationally. And that looked really good.

AG: Speaking of generations, both of you have been prominent influences and invaluable leaders in the LGBT community for decades.

KB: We are important in different spheres. One of the first things we realized when we sat down and talked with each other over Szechuan food a year and a half ago ...

AG: You never met prior? Was there beef?

KB: [Laughs] We knew each other's work, of course, but we were still wary of each other back then. We disagree on so many things. And when we finally sat down, we realized that we wished we had each others' friendship.

JB: And readership. Kate has an audience, probably more queer-identifying and radical. And I tend to have nice book-club moms from Iowa. [Laughter]

Courtesy Kate Bornstein

Jennifer Finney Boylan, left, and Kate Bornstein, transgender activists and co-stars on "I Am Cait."

KB: You say that in a self-disparaging way. You write for the f---ing New York Times.

JB: Many, many cis and straight people have come to their first understanding of trans issues through Kate's work. Kate opened the door to a lot of so-called mainstream readers.

AG: Did either of you ever feel any sort of burden of responsibility in representing the LGBT community? Especially for trans folks, who are so chronically misrepresented?

KB: I always saw it as my great joy as "Auntie Kate" to be there in person for kids and for our family. I see us not so much as a "community" as we are a family. Because I'm old, I can't do it much anymore, it takes so much out of me. But I miss it, being there for people.

JB: Kate's work, even if she is not doing as much of the live stuff right now, goes on in her books. My favorite of hers is "Hello Cruel World," which was designed to combat teen suicide.

I want to counter the idea that we are particularly interesting. The world is full of many, many boring gay people and our work will be complete when trans people are boring, too.
Jennifer Finney Boylan

KB: I examined books written on suicide prevention and they were boring. They wanted you to be good and then they would proceed to tell you what good is. And I thought, no. The only other option was just make your life better, do anything to make your life better with one rule: Don't be mean.

JB: The book is a wickedly mischievous embracing of life and pressing back against the darkness, it's a book to keep young people from despairing. I don't exactly do that. I write from a very personal space.

KB: You open people's hearts. That's what you do. You say, 'Look, this is my story. I have a wife, I have kids, I face the same things that you face.' You open up a space in people's hearts for trans folk.

JB: A thing I get a lot from people is, "When I read your book, I knew that suddenly there was someone who was trans who seemed normal." And I'll put that word "normal" in quotes, because I think that's a hot-button word. But people say that to me, and they mean well. My story is just about someone who is surviving and who went on to live a happy life. And when you were asking before about responsibility, it's a thing that gives me pause because I know so many people in our community don't land where I landed.

AG: True. Violence against trans men and women remains frequent and overlooked. More than one in four trans people has faced a bias-driven assault. The Human Rights Campaign reported record rates of trans homicide victims in 2015, and among the 53 trans people murdered between 2013-2015, not one of the cases was reported as a hate crime.

JB: I wrote a piece for the Times last August, and at the time I think we were up to about 20 trans women who'd been murdered since January.

AG: In that article you juxtaposed what each woman was doing on the day she was killed with what you were doing.

JB: Yes, so it would read, "Jan. 1, I moved to New York City to begin a new job at Barnard College and my son came with me. We went out for Ethiopian food. Meanwhile in Chicago, so and so was murdered by her boyfriend." It was a way for me to interrogate my own privilege, contrasting that with all of these trans women, mostly trans women of color, who were being slaughtered. Here I am, and here they are not. And did my life matter so much more than theirs?

AG: It's a very different message than the one Caitlyn Jenner is delivering via her reality show, where much of the messaging is that trans life can be mostly rainbows and kittens.

JB: I'm happy to send out a positive message and say you can be a trans person and your life can be good. But I don't want to sound facile or unaware of the fact that for many of us life is really hard and for some people life is the thing we have lost.

AG: When did you both decide that you would become public figures and advocates?

JB: I don't think I ever decided. I wrote my memoir, "She's Not There," in a summerhouse in the middle of winter in complete isolation. I had no idea that it would ever see the light of day or that anyone would ever read it. The publisher didn't particularly think a semi-comic story of changing genders was an automatic best-seller. The book's success took me by surprise, took the publisher by surprise, and kind of catapulted me into a role for which I was not particularly prepared.

AG: How did you handle it?

JB: I think, to be quite honest, I used to speak about my own experience as if I was kind of better than everybody else because I was very proud of myself having negotiated all this stuff. As time has gone on, I've tried to be more aware of how my story fits into the overall mosaic of the many, many ways there are to be trans and that they are all cool.

KB: When I came out, I was doing the chat shows, way back in the '90s. Geraldo, Joan Rivers. I was on Phil Donahue. A lot of the morning shows. These were precursors to reality TV.

AG: Did you ever feel like you were being trotted out as the "freak of the week"?

KB: In the 19th and early 20th centuries, the freaks were never allowed to talk, it was always the barker who would talk about the freaks. And the chat shows turned that around and the freaks were invited to speak about themselves. I took that as welcoming! I will say that when my book "Gender Outlaw" came out in 1994, I got pegged as the expert. That scared the f--- out of me and I ran away from that, which is why in subsequent books I quote hundreds of trans people to make sure that other voices are heard. And I think Caitlyn has the same intention to do that.

AG: It seems like, regardless of her politics and controversies, you both have genuine affection for Caitlyn.

KB: Oh yeah.

JB: And that makes some people very, very upset that two old radicals like us would embrace not just a reality TV show on E!, but also Caitlyn Jenner. But I believe she is genuine in her desire to help people and she is genuine in her desire to learn. She doesn't know what she doesn't know and that's an issue, but she is trying. I really do think of her as a friend.

AG: Do you see parts of yourself in her at all?

KB: She is exactly my generation. She and I began our transitions in the same year, 1984. Two years later she stopped. And two years later I went through with genital surgery. We've shared the same transition from privileged, white, heterosexual guy to lesbian. The difference is not having had the internet, not having had many source books, I had to dive into the queer community to discover anything. Doris Fish, drag queen, super star of San Francisco, was my drag mom and she taught me stuff and so did other drag queens. So there was a blending of values that Caitlyn isn't getting. Drag was brand new to her. She's never really had the chance to sit down and talk with people.

AG: She is also insulated by her celebrity.

JB: She is insulated. Part of the way we become ourselves is through trial and error. And part of the trial and error involves being in the world with other people. That's very hard for her. When you're a celebrity, when you're older, when you're wealthy, there are fewer opportunities to realize your mistakes.

You open people's hearts. That's what you do. You say, look, this is my story. I have a wife, I have kids, I face the same things that you face. You open up a space in people's hearts for trans folk.
Kate Bornstein

AG: What kind of mistakes do you see her making?

JB: I don't mean saying the wrong thing and having to apologize as much as I mean your sense of, who am I in the world? I remember back in the days when my female existence consisted primarily of cross-dressing in a room with a locked door. I'd go through this whole presto-change-o thing and then it would be -- finally, finally I'm myself! And then the question would come, which is, Who, exactly? I did not have that answer.

AG: Where was this?

JB: In a room in a small town in Maine behind a locked door and on the other side of the door was four feet of snow. The shock when I finally went through that door, literally. My first few outings it was like, holy cow, the wind is really cold when you're not wearing pants. Or, these heels are hard to walk in.

KB: That's the level of stuff that you're dealing with. When Caitlyn infamously answered that question -- "The hardest thing about being a woman is figuring out what to wear" -- well, that's true for her. For Caitlyn, that was the hardest thing. She had no idea what to even put on her body. Can you imagine being an adult and not knowing how to dress yourself? This is a big deal.

AG: Women reacted very strongly to that comment.

JB: I think she meant it to some degree ironically, but it's no joke.

KB: And then she made the observation about people "getting upset when they see what looks like a man in a dress."

AG: Which also went over about as well as clogged plumbing on a cruise.

KB: But ... it's true. There is nothing false about that statement. What are you going to argue? That people don't get upset? They do.

JB: These comments are just Caitlyn's reflex to "normalize" an issue. Those are her words.

AG: Being perceived as normal is a big concern for Caitlyn on the show.

KB: She doesn't understand the struggle we have. I think she is just now beginning to get the reality that a lot of people don't like us. [Laughs] She's never been in the position of not being the good guy, the adored one.

AG: An Olympic champion. On a Wheaties box. A hero. Part of the world's most famous family.

KB: And handsome and personable.

JB: Caitlyn believes her personal charm will solve almost any situation she is in. She really believes that if there are people who hate us, they just haven't met her yet.

KB: We were trying the whole season to get her to speak with a real rabid conservative. That never happened. Real rabid conservatives didn't want to talk with her. They don't want to be seen with us.

JB: So yes, I see plenty of myself in her. I remember when I had [gender reassignment] surgery, some flowers arrived from a friend, another transgender woman, and the balloons said, "It's a girl!" which I thought was very cute, and the card read, "Now the journey really begins." And my first thought was, f--- you. The journey? Really? Now? I've been through this really hard and difficult thing and finally I've had surgery, which I've been waiting for nearly 40 years and you're telling me now the journey begins? I want the journey to be over. I want to just live my life and have fun and not have to worry about the gender thing ever again.

Paul Drinkwater/NBCUniversal

From left, "I Am Cait" stars Candis Cayne, Jennifer Finney Boylan, Caitlyn Jenner, Ella Giselle and Chandi Moore on a press tour for the show.

AG: Caitlyn seems to be in a similar frame of mind.

JB: Yes. But for me, the journey did kind of begin after. Not of becoming a woman, although there was a little of that, but the journey of knowing what to do with myself now that I was a woman. I was telling that story before about how I used to stand on one side of the door and ask who am I? The answer turned out to be, to my shock, to some degree the person I'd always been. Caitlyn has only begun to walk through that door.

KB: Nobody has ever done the kind of transition she's doing. Do I see her dealing with the same issues? Absolutely. I smile inside every time she says she is her authentic self. I say, "Oh baby, wait till you see your next authentic self. [Laughter] I'm fond of Caitlyn like a kid sister. She is a good sport and if you're not being mean to her you can say whatever you want and she'll laugh with you. I've seen her be a champion these days, too.

AG: If you could correct one misperception about the trans community what would it be?

KB: That it's in any way monolithic.

JB: I want to counter the idea that we are particularly interesting. [Laughter] The world is full of many, many boring gay people and our work will be complete when trans people are boring, too.

AG: How difficult is it to see that even with so much increased trans visibility, there is a rise in discriminatory laws such as those in North Carolina, Tennessee and many other states? In 2016, state legislatures introduced 175 anti-trans bills, many of which allow legal discrimination, such as the so-called "bathroom bills." Never mind that there has never been a single reported incidence of a trans person raping or assaulting anyone in a bathroom.

KB: What we're seeing is a fascistic response to no problem at all.

AG: Last December, a trans woman named Meagan Taylor was arrested while she was trying to check into a Des Moines, Iowa, hotel because her ID listed her as male. The hotel manager called 911, and Taylor was arrested for no discernible crime and put in jail for eight days, causing her to miss the funeral she was traveling to attend. Sadly, cases like these are not unusual.

JB: I've heard people compare this moment, the North Carolina moment, to the Prop 8 moment in California. It would be nice if progress were always forward. But progress tends to be more up and down. It may be the backlash to the North Carolina law and those like it will not only galvanize sensibility, but make people realize all the lies that are being told not just about trans people but everyone else who is affected by it.

Santiago Felipe

Kate Bornstein

AG: Switching from state politics to the more personal, women and girls are often merciless when it comes to their bodies. How have your relationships with your own bodies changed over the years? Where do they stand now?

KB: I started cutting when I was 14. And I began a lifetime of anorexia in my senior year of high school. I would jog miles and miles every day and not eat. Buddhists say that the root of all suffering is grasping. Grasping to be the perfect beauty, the slender, young blonde -- that would make me suffer a great deal. Nothing about my body was right, nothing about my body said "pretty girl" like I saw on television. And it just kept getting worse with age. I did the cross-dressing in the hotel, behind-closed-doors thing. And I looked longingly at the beautiful drag queens, but I wasn't brave enough to do that. I liked the idea of drag because that seemed to be the only way I could go without admitting to myself at the time I was a complete freak and a transsexual.

JB: You thought being a transsexual was worse than being a drag queen?

KB: Yes, at the time, transsexuality was worse. I would've rather been a drag queen. Drag queens to me always represented a life of fluidity. And transsexuality always represented a commitment. [Laughter]

AG: Kate, to be clear, you now and have for quite some time embraced the word "freak," and are proud of belonging on what some would call the island of misfit toys.

KB: I've said before, we should stop "tolerating" or "accepting" difference, as if we are so much better off for not being different in the first place. We should celebrate difference. No question containing either/or warrants a serious answer, and that includes questions of gender.

JB: This is exactly where our views are different in that I always had a binary sense of my own gender. Who do I want to be? Who did I always want to be? Female. So to me transsexual was the default. My gender is in some ways very boring, which is just what I always wanted. I felt bad for drag queens because at the end of the day they had to stop being women, poor things. I don't want to define myself in terms of who I'm not.

I Am Cait/ E! Entertainment Television

Kate Bornstein on "I Am Cait."

KB: Whereas, I do want to define myself by who I'm not. I know I am not a man, I know I am not a woman. Beyond that it's all theory. Every time I define myself by what I am, I feel trapped. I had to learn to radically accept my body for what it is and get on with my life. I had it in my head, "Who would love a freak like me?" You're never going to have a lover. But I have been blessed with people who have loved me and my body just the way it is. When I was young, I never would have predicted that.

JB: When I went through transition I was in my late 30s and hormones had an initial effect of making me seem much younger. I lost a lot of weight. I was like a size 8, which is small if you're 6 feet tall. I had a brief, happy period, kind of like Caitlyn is now. I felt really cute. I had a lot of really cool clothes and I loved to wear them. I was often propositioned if I was in a hotel by myself, sitting having dinner. So there was a lot of action for Professor Boylan at a certain point. [Laughter] Now I am aware that as a woman, I'm not who I was. I've put on a lot of weight, which I don't like and which I am incapable of losing. It's a little hard, aging.

We should stop 'tolerating' or 'accepting' difference, as if we are so much better off for not being different in the first place. We should celebrate difference. No question containing either/or warrants a serious answer, and that includes questions of gender.
Kate Bornstein

AG: Australian feminist Germaine Greer recently gave another speech where she argued that transwomen are not "real" women and that men "deciding" to be women is "unfair." Is this criticism you two hear often?

KB: I remember as early as six months after my surgery, people kept questioning me: How can you be a woman the way we are? You haven't been raised, haven't been socialized, haven't had the same kind of hormones. You've had a lot more privilege and entitlement.

AG: How did you feel hearing those questions?

KB: I was grateful for them. They got me to question myself much more deeply. I was still holding onto an approved identity.

JB: My experience post-surgery was very different from Kate's. From the moment I came out of anesthesia, my sense was, ahhh, there we go. It was not like, now I am so beautiful, it was like, now I am finally my own damn self and I can stop worrying about it. It's important to consider what it means to grow up with a uterus, to grow up vulnerable and in danger from the male gaze. But I also feel like people who interrogate my womanhood based on various yardsticks do a lot of damage. I mean, those are good questions to ask, but for me the end point of that inquiry should not be: So, therefore you're not a woman. For me, the end point is: So, therefore your experience has been different than that of other women -- not to tell us that we are not who we say we are.

AG: People with transphobia do seem to spend a great deal of time trying to debunk the gender of trans men and women ...

KB: But the reality is, what something is now isn't what it was a millisecond ago. It's always changing. Everything starts as something and continues to become something else.

AG: How do you see yourself now?

KB: My current identity is little old lady. And I return to the radical acceptance thing. Is old age fun? Best time of my life. OK, everything hurts. I'm on painkillers a lot of the time. And people are dying. Friends. They're going. That part is really, really hard. But I think that's one of life's biggest lessons. We get a chance to learn that none of those downers outweighs the joy of perspective.

JB: When you sense the pieces of the jigsaw puzzle falling into place.

AG: The "Joy of Perspective" sounds like a self-help book I would actually read. I look forward to your older women's empowerment speaking tour!

JB: [Laughs] We totally should do that! That would be a ton of trouble, wouldn't it?

KB: But could we stay on the road with each other for that long?

JB: Well, we survived that f---ing bus. We can survive anything.

Related Content