From left: Caitlyn Jenner and Prof. Jennifer Finney Boylan. Photograph by Andrea Metz.


I am Cait was one of the summer's most talked-about shows, and Barnard's first Anna Quindlen Writer-in-Residence, Jennifer Finney Boylan, played a starring role. The reality show followed Caitlyn Jenner, formerly known as Bruce Jenner, the Olympic athlete, as she learned to navigate the world as a woman after coming out as transgender. On set and on-screen, Boylan served as Jenner's advisor, helping her figure out, as Boylan writes on her blog, how she wants "to live in the world." Below, Boylan answers questions about getting to know Jenner, and what it's really like to be on a reality TV show.

You’re a writer and a professor—so we’d imagine that being on TV was a very different experience than you’re used to. What was the most surprising thing about being a regular on a TV show?

What was the thing they used to say about Vietnam? Hours and hours of sheer boredom, punctuated by a few seconds of extreme terror? Something like that. There was a lot of sitting around, during which time I read The Collected Stories of Ring Lardner. Then the scene starts and you have to throw your heart into it. And in fact, some total stranger’s complete understanding of trans identity is dependent upon your speaking eloquently and honestly.

None of the show was scripted, and we frequently had no idea what was going to happen next. I kept feeling compelled to haul the conversation to a level that mattered—to get us away from hairspray and on to something of more consequence. (Not that hairspray, in a few circumstances, was not a matter of utmost urgency.) But I was aware that this was a show in which the consequences were high. In the very first scene in episode one, we saw Caitlyn without any makeup at 4 a.m., freaking out, saying “I hope I get it right. I just want to get it right.” And yet, how could she be expected to “get it right,” when she is even now still learning what “it” is. Transgender people coming out go through a certain adolescence, trying on various selves, moving through narcissism and toward truth. Most people have the luxury of getting through the awkward time in private, but Cait was filmed in all her naiveté, learning, figuring out a very new and confusing world—not just transness, but womanhood, in all its glorious contradictory wonder.  

What was the most fun about it?

Well, I did do some things I would never have done otherwise. I went moto-cross racing with a dozen transgender women, for instance. (Don’t ask.) I ate pork chops with Boy George. I went disco roller-skating. I also made friends with people in the community whom I have known of for years but never met, especially Candis Cayne, who turned out to be one of the most genuine, kind people I’ve ever met.

But the real “fun”—if you’ll forgive me being an English teacher all over again—was the sense of changing the culture a little bit. The show—and Caitlyn herself—has taken flak for emphasizing one particular part of the trans experience, that of a privileged white person of considerable means. And that criticism is fair. Still, Cailtyn’s transition was going to be front-page news no matter what she did. And so instead, she decided to use her celebrity for good,to shine a light on trans experience, and to populate her show with lots of people outside her own world. And so you had me—the writer from New York (and Maine); you had Jen Richards, an activist from Chicago; Chandi Moore, a trans woman of color from L.A. who works with homeless youth; and Candis Cayne, a performer and a singer. It was like the Gilligan’s Island of the transgender world. I wanted to be Ginger. But of course, I wound up as the Professor. Same as always. 

Anyway, I really do think there is a tremendous power in visibility—which this show certainly had. The show was for an audience of people who may have never given two seconds' thought to the realities of trans people’s lives before. I know we got through to those people because I get letters from them every day, saying how their eyes have been opened, and not just to Cait’s particular world, but to all of ours. That’s good work. 

What role were you able to play for Caitlyn—for instance, one article described you as being a “check” for her—and how do you think it helped her personal journey?

My role on the show was The Voice of Reason. (I told my friend Richard Russo about this, and he almost laughed so hard his beer came out of his nose. “YOU?” he shouted, “The Voice of Reason?”) But Cait’s surrounded by a lot of glamor-pusses—I think my role was to try, very gently, to inject her with a little “serum of feminism.” I’m glad she’s got eight million shoes, but if the transition is only about shoes and underpants, it’s going to fail. I tried to make her understand what trans people without her own particularly curious form of privilege go through—especially trans women of color, who are victims of violence, homelessness, and unemployment, at astronomical rates. In the end, I think she got it, or started to.  I’m hoping that work continues, because the real life-and-death work is what really matters here. We need to educate people about trans lives—our dignity and struggle. We need to stop people from being murdered. We need to give young people the hope that will put an end to the rash of suicides. 

Did you get the chance to say anything to the world (via Cait) that you’re glad you had the chance to say? Anything you regret?

I had a pretty intense back-and-forth one day when we were talking about sexuality, and she said she wasn’t sure if she wanted to be with a man or a woman, but that being with a man might make her feel more “normal,” because a man would make her feel more “like a woman.” I kind of took her to task for this, asking, “What’s this ‘normal’ you’re talking about?” And telling her you don’t need a man to make you feel like a woman—that our sense of self ought to come from within, and that we shouldn’t seek approval or verification of our identity from others.   

I might have been a little harsh with her, which I feel bad about, but that conversation hit a nerve, and I felt like, “Well, I’m supposed to be the Voice of Reason on this show, so I guess I gotta give her hell now." The Voice of Reason thing is actually very funny. Like, how did THAT become my role? I don’t know, maybe because Diva was a slot they’d already filled?

Regrets? There was a scene in the second episode where they were giving me a makeover, and I was complaining all the way, from the moment they glued in the first eyelash to the second they took out the last hot roller. I said, “I can feel my I.Q. plummeting!” Which was supposed to be a joke, ha-ha, but I think in that scene I come off as judgmental, especially to people who are high femme. Who have every right to be fabulous and beautiful as I do to be dreary Mrs. Bookworm. I do think I have the Mrs. Bookworm thing down solid though.  

What would you consider the main thing you learned while working on the show and advising Cait?

I was reminded yet again during the process of making this series, that there are an awful lot of ways to be human. Cait’s way of being trans—or of that matter, of being a woman—is not mine; she cares about a whole bunch of things—makeup, hair, beauty—that I admit I don’t lose a lot of sleep over. But to Cait it was important—and to a lot of women—and for that matter, men—it’s important, and it was valuable to be reminded that my own particular way of looking at the world is not the only one there is.  I’ve learned this about transgender people over the last decade and a half—for some people, being trans is about occupying a non-binary, fluid embodiment; for others, it’s a “condition” like cleft palette that you get through as swiftly and efficiently as possible; for a third set of people it’s an identity largely grounded in theory and political struggle; for yet another group it’s a wild party where you bring your feather boa. There are people who want to be “outlaws” and there are people who want to blend invisibly in with others. I worked with a dozen other trans men and women on the show this spring and summer, and not one of them particularly reflected my own “take” on being trans, and Caitlyn Jenner least of all.  There’s a saying: “If you’ve met one trans person, you’ve met—one trans person.” I was continually reminded, during this show, that there are a million different ways of living your truth. 

Is there anything you learned or picked up on the show that will help you specifically with your writing and teaching going forward?

I wouldn’t say specifically, because helping Barnard students learn to write is a whole different animal than walking a celebrity through a coming-out process.  I would say that the whole thing demanded a fair amount of patience and good will and trust in the goodness of the human spirit, though. And those are pretty good tools to be carrying around, not only in the classroom, but in the rest of your life as well.

How did you become involved with the show in the first place?

I had been asked by ABC News to participate in a Diane Sawyer special about transgender issues. It actually took three or four calls before I began to realize that we weren’t talking about transgender issues “in general” and that we were really speaking about one trans person in particular.  Anyway, I must have failed to make a bad impression in that interview— which was filmed at Barnard, by the way, and which featured a few quick shots of me teaching a class in Barnard Hall—because the producers of the docu-series had me all lined up as a consultant before the Diane Sawyer special had even aired. I’m not sure if I remember how I morphed from “consultant” to an actual member of the cast. Mostly what I wanted to do was to be a friend to Caitlyn. She seemed so incredibly isolated and alone to me—we talked on the phone throughout the spring, and I tried to let her know that, as solitary as she felt, she was walking on a path that others have walked before her—hundreds and hundreds of thousands of us by now. Being trans is hard enough, but when coupled with the “bubble” that Cait lives in— well I just feared she’d never know what it’s like to have a normal morning where you wake up and you don’t have to think about gender. Quite frankly, I still fear that for her. But her fate and her future are now her own.