TV interview

Meet Jenny Boylan, Caitlyn Jenner’s Voice of Reason

The Daily Beast

March 11, 2016

Caitlyn Jenner’s Republicanism is well-documented, but until a recent interview in the Advocate, few were aware she wanted to be Ted Cruz’s “trans ambassador” should he become president.

The former Olympian and reality TV star seems not to know about Cruz’s anti-LGBT record and his intention—should he win the presidency—to scrap marriage equality.

In the first episode of the second season of her E! reality show, I Am Cait last Sunday, which features Jenner and a group of buddies laughing, arguing, and talking politics on a cross-country bus trip, Jenner claimed that Republicans were just fine on LGBT issues.

“None of the Republicans are ‘I hate trans people’ or ‘I hate gays,’” she said. “They do nothing of that. I want a driving economy so every trans person has a job.” And, “if our country collapses, it doesn’t make any difference if you’re gay, trans, whatever.”

The only voice raised against Jenner’s baffling, fact-defying reading of contemporary and historical Republican LGBT attitudes was that of the author, activist, and teacher Jenny Boylan (full name: Jennifer Finney Boylan).

Boylan’s mouth fell open in horror and disbelief—just as many of ours did—as she took Jenner to task on her willful political and cultural myopia. (The other women on the bus are Kate Bornstein, Candis Cayne, Chandi Moore, and Ella Giselle.)

Boylan later spoke by phone to The Daily Beast about Jenner, Jenner’s politics, their friendship, why she got on so well with Kris Jenner—and what happens when “Glam Jenny” comes out to play.

What is going on with Caitlyn? Does she really believe Ted Cruz and the GOP are LGBT-friendly?

In some ways, this is the most subversive progressive program on television right now. This is a reality TV show on E! with a conservative Tea Party Republican as its star. It’s such a strange, unlikely combination of events. In its own way, I Am Cait is more progressive than Rachel Maddow’s [MSNBC] show.

On the strength of Sunday’s show, Caitlyn seemed pretty clueless and ignorant.

The show is not actually about her. I know it’s called I Am Cait, but the first season was very much about trans issues—or “the issue,” as Cait calls it—and there was rightfully a lot of fear about getting it wrong.

This season is getting to some very complex conversations, and not just about being trans but also about the life of the country.

The trans community is diverse, from genderqueer people to male-to-female to female-to-male, to gender non-conforming, to drag queens and drag kings and cross dressers and everyone in between.

One person might say they’re about viewing sex and gender through intersectionality; someone else that it’s a medical condition; someone else that it’s about rejecting the binary and finding peace according to your own likes; someone else that it’s a party, get out your sequins.

Caitlyn Jenner is attracted to men and really cares about her hair being beautiful. I don’t particularly care about being pretty. What I care about is raising children. I’m attracted to women, I’m a lesbian married to a woman for nearly 30 years.

The women on the bus themselves are very different.

All of us have different senses of being trans and get into arguments about that. You’ll hear a very contentious conversation about the word “tranny,” which I and many trans women consider a slur. The only association I have for it is as a word used against me when I was beaten up. But some people on the bus are outraged that we have been asked not to use that word.

OK, so you mean there are many different kind of trans, of which a right-wing Republican like Caitlyn Jenner is just one.

The show is about how we learn to talk to one another in this country right now.

I’m going to sound like a maniac, but we have to learn how to treat each other with love: Republicans, Democrats, and everything in between. We have to learn to talk to each other, so our lives are not one long Internet scream-a-rama. I would say my behavior on the bus towards Cait was not a good example of how to behave.

I disagree. You were great. The issue isn’t that she is Republican—there are many LGBT Republicans. The issue is her ignorance around the LGBT and trans-phobia of who she’s supporting. Is she ignorant of the facts, or does she just not want to know?

That’s a good question.

She went on about her belief in Republican economics—does her belief in whatever that is outweigh her belief in LGBT rights?

I guess. I disagree with her that electing Hillary [Clinton] and Bernie [Sanders] would equal economic catastrophe. I disagree with her big assumption that somehow Cruz or [Donald] Trump’s economic genius is so great that it outweighs fighting for candidates who fight for your own people. Is it ignorance or will? I just don’t know.

Did she know what Ted Cruz had said in the past? Is she ignorant of that?

As of that day I’m not sure she actually knew. I think she listens to a lot of Fox News. I think people who listen to Fox News think they are well informed because they have this television on shouting at them all the time. When she said, “Republicans support everybody’s rights,” that was the moment I jumped up and said, “That is a lie. That has never been true. That’s never going to happen.”

What did you think at that moment?

That I wished I hadn’t agreed to be on this show. On Day 2 or 3, on camera, I quit the show. I said, “I cannot do this,” because I didn’t want to fight about politics all the way to Chicago. Actually, I’m not an argumentative person—generally I’m very afraid of conflict and pretty conciliatory in my general views. My main goal is how to get people to love each other. Instead, here I was shouting at her.

You were quite right to.

I didn’t like the person I was becoming.

We did. You were the only person on that bus challenging her.

Kate Bornstein had her hand over her mouth muttering, “Oh dear, oh dear.” Candis [Cayne] got up and left. To be fair, later on you’ll see other people picking up the mantle. The role that has been cast for me has been for Cait’s smart, argumentative friend. The show is not rehearsed or scripted.

Is it fairly edited?

Yes, I think they make me look better than I actually am. What you hear from Cait is the way a lot of LGBT Republicans talk: “We all believe in everyone’s rights, but we need to reduce the national debt.” Cait does say she knows Democrats have been better on LGBT issues. She doesn’t seem to want to acknowledge that difference matters a lot. Maybe if you’re conservative you don’t want to acknowledge that difference matters. To me, difference makes all the difference in the world.

So, it’s for LGBTs to accept that Jenner is not going to be the say-the-right-thing ambassador?

Caitlyn Jenner is our star, but she is a very problematic star, and my prediction is she will always be problematic. This is not the last celebrity that will come out as transgender.

We can’t choose who comes out as trans, but I have to say, and this is me speaking in defense of her to some degree, we’ve got her, like her or not.

Many in my community feel like, “Well, I don’t like her,” and that she should be isolated, shunned, and made to shut up—especially since the Cruz thing came out. People are like, “We’re really done with her,” including friends of mine who’ve said, “Boylan, you know I love you, but I’m not watching your fucking show. Jenner is too problematic: She hasn’t been out that long, but certainly around long enough not to be the champion of people out to destroy us.”

For all of that, I’m very fond of her. She is my friend. She really wants to do good. She knew her transition was going to be front-page news. As a result of her own fame as an athlete and the weird fame of her family, she made the decision to do this very publicly and in a way she hoped would improve the lives of transgender people. I think the visibility of Cait still outweighs any awkwardness resulting from what comes out of her mouth. It won’t be true forever, but it’s true for now.

What is she really like?

She is earnest, hopeful, obsessed with her hair and makeup. She has a head like a rock. It’s hard to get through to her or change her mind, but she also has a very big heart. My wife and I were in Paris [before the terrorist attacks there], and people stopped us on the street and told us how much good it was doing, and how it changed their minds and opened their hearts.

The day after Caitlyn Jenner came out, everyone knew someone who was transgender in the United States.

I would be happier [if] everyone knew someone who was more articulate and whose lived experience before indicated a better sophistication and familiarity with feminism and what being a woman means.

But Cait is whom we have been given, and I’m so grateful for the good she is trying to do. She may find her own politics at some point hold her back. What being conservative means may change for her. We shall see.

So does she change in this season or stay rigid in her love of Republican ideology?

I think you will see her change. At the end of this season, she is still a Republican, you’ll be shocked to learn [laughs], but the way we speak to each other changes…and you will see Caitlyn Jenner learning, dear God, to listen.

Has doing I Am Cait changed you?

I wasn’t supposed to be on camera. I’m not a TV natural. I had been talking to Cait on the phone for year before she came out. I was trying to counsel her, then fell into a consultant role on the show.

This season, we were trapped together 24 hours a day. I was pretty miserable doing it. I didn’t like all the yelling. I was homesick. I didn’t feel like anyone else saw the world the way I did. One night, I was crying, “I want to go home. I feel so alone on this trip,” and Candis said, “That’s what I was thinking.”

I know people wonder what is real on a reality show. But I hope people do not question the love between the women on that show.

The young girl, Ella Giselle, is like a young ingénue from a whole different generation where coming out as trans is far from easy, but not like the world I had to come out to.

What has being on a reality show taught you?

[Laughs] To stay off TV. I tell you one thing: Caitlyn Jenner brings out the crazy in people. If she sneezes, the Internet explodes. All she has to do is fart and there will be 100 angry blog posts about it. I’m not downplaying the importance of what people write about her or making light of the ways she is problematic, but she really does drive people crazy.

What’s behind that?

In the trans community, people have this desperate sense to be known. Coming out as trans, you’re fighting for your identity. So the idea of someone else coming out and coming between you and the world, of interfering, smudging the way you wish to be seen, is difficult.

Every six months a celebrity comes out as trans, CNN follows them around, and I sometimes wonder if the camera isn’t a big mirror for them in the world. They might be better off being quiet and reflective. In the culture we live in, the way you see yourself is by putting yourself in the position where other people see you—and that, I think, is dangerous.

So would Caitlyn Jenner have been better to have been more private?

I think she would have, but that was never going to happen. If she hadn’t done what she did, she would have been hounded. Now she controls a lot of her story, she doesn’t do that many interviews. She controls her image pretty carefully.

She knows who she is but doesn’t know what it means to be herself in the world, and it’s unfortunate if you live in that bubble. It’s very hard for her to experience the world without being followed all the time. It was going to be a bloodbath whichever way she came out. At least this way she controls her story and does some good.

What was Kris Jenner like?

Honestly, my first thought was, “Ah, the brains of the family.” That isn’t a slight against Caitlyn, but Kris is very smart. She was very welcoming to me. I can’t tell you if she actually liked me, or if this was a move in the chess game of the Kardashian-Jenner family. I felt like we had a real rapport. I probably had the most interesting discussion of the entire show with her.

Why so? What about?

We sat on the couch and questioned the value of fashion. Kris said it was the way women could take control of how they were perceived and have fun doing it.

I said, yeah, but it encouraged people to judge each other based on appearances.

She said we all had to look like something.

I said, yeah, but that it cost tremendous amounts of money to care about fashion, so if you participate in this, you are participating in a system of privilege.

She didn’t dismiss me. She got right on in there and rolled up her sleeves. It’s a conversation I could never have with Cailtyn. The only thing she says is, “All I know is, you’ve got to work it.”

Kris seemed to have a negative response initially. Has she come around to Caitlyn being trans?

She and Cait have a disagreement about who knew what when. Caitlyn says, “You know I told you,” and Kris says, “You never did.” I think it’s possible—and I’ve seen this with other marriages, including my own—that both may be true.

One person either told the other, or thought they did, or almost did, and the other person listened, or didn’t listen, or forgot, or it changed in their mind. You’ll never untangle it.

But Kris was certainly more eager to hang out with us than she was to hang out with Caitlyn. She turns up in the New Orleans episode, which—among other things—features the appearance of “Glam Jenny.”

I knew it! You do like fashion after all.

In New Orleans, I went to the makeup people and said, “All right, screw it. Give me the works.” Three hours later, I walked down the hallway in this amazing dress. I didn’t know Kris Jenner was there. She said, “Oh, look, a woman after my own heart.”

You seem to be the show’s voice of common sense.

I don’t think of myself as reasonable. Does that make me less fun? Certainly there are times when everyone is talking about boyfriends and mascara, and I’m thinking, “Maybe our lives should be about a little bit more.”

They would find me reading my book at the back of the bus and say, “Jenny, what are you doing? You know we’re making a television show. Go in there and talk about sexuality.”

I had a reputation for complaining about everything. In one scene they wanted us to go a Chicago drag show, and I said I wouldn’t go, I didn’t want people thinking we were “impersonating” women ourselves.

Of course we end up doing it, and it’s one of the best things on the show.

Do Candis and Caitlyn have a real chemistry? Do you think they’ll end up together?

Oh my God, that’s a really hard question. On the top level, yes there’s a lot of chemistry there. Those two are the closest friends on the show. They see each other all the time when the show is not filming.

We know Candis is attracted to men almost exclusively. Caitlyn said that if she dated someone else, it would be a man, so Caitlyn is saying she too is straight. But the things she wants from being with a man are things about the way she wants to be treated. She wants someone to hold the door open, to pick up the checks, to treat her “like a lady,” whatever the hell that means.

It doesn’t seem like having a sexual relationship with a man has anything to do with her stated desire to be with a man.

If that’s what she thinks sexuality is about, it makes me want to say, “Maybe you’re not as heterosexual as you think you are.” If in her heart of hearts she is really drawn to women, maybe there is more to that electricity between Candis and Caitlyn, at least on Caitlyn’s side.

Who or what does Caitlyn want sexually or romantically?

I don’t know and would not speculate. I think the main object of her desire right now is herself. She is absolutely focused on her own experience as a woman in the world. Dating someone else seems pretty far off the radar.

Is being in love important to her?

It certainly seemed important in the past. Caitlyn said to me, “I’ve got three ex-wives.” I said, “Well, now you can get an ex-husband.” She’ll find out in her own sweet time.

My wife is a very different kind of woman to Kris Jenner. Seeing me through on my journey was something she wanted to participate in. I didn’t know right away if we would stay together. Then, one or two years after transitioning, it was clear we realized that we were better together.

Does Caitlyn Jenner accrue knowledge this season? It hasn’t started that well for her.

She certainly does. Cait is a kind of ringleader, but a lot of the drama is about each of us. Each of us becomes our own Kardashian. I don’t know which Kardashian I am.

Someone said to me they thought I was Scott Disick, Kourtney’s ex, who joins us for a while. It was clear he was looking to Caitlyn as a parental figure, a mother figure, but Caitlyn has very mixed feelings about him.

Instead, Scott Disick finds me.

What? You pal up?

Yes, for an extended period Scott Disick and I hang out. There’s a curious energy there. My heart really went out to him: He seemed so hungry and longing, looking for something Caitlyn can’t give him.

He’d just got out of rehab, and I said that if he could stay sober for a year, the very next day he should propose to Kourtney and be a father to his children. [Laughs] He said, “You really don’t want watch the Kardashian show, do you?” and looked at me like I was from Mars.

So, will you return for Season 3?

[Laughs] It was really hard doing this. I was unhappy for long stretches doing it. On the other hand, looking at it now it looks really good. I really believe we’re on to something—not just in terms of trans visibility but showing how people can come together and learn to talk to each other.

And you’re a writer and public figure—it’s good for your own visibility.

Yeah, but on the other hand I’ve published a dozen books, I’m a contributing opinion writer for The New York Times, I’m a co-chair of GLAAD. It’s not like I’m hiding my light under a bushel. This enables me to reach a different kind of audience, and I’m grateful for that.

A lot of people are angry with me for participating in this. They think of Caitlyn as an incredibly flawed figure. People think I am a sellout. If only they knew how incredibly little I’m getting paid for doing this thing, and how many gray hairs it has caused me, they might think twice.

I think you liked “Glam Jenny.” Has the show made you vainer, and more aware of appearance?

Candis takes me under her wing in one episode. She takes me shopping for lingerie. I’m all grumpy. My wife and I, our relationship, is not about underwear. But by the end of that scene, when everyone else has given up and left, we’re picking up cute things—a nightie and all sorts of slutty things to get me into.

So did I change the way I feel about my appearance, or become more vain? No, but I am a better friend to people who care about these things. I’m less judgmental. I hope this whole experience has made me less judgmental and more openhearted. But I’m not the judge of that. Call me back in seven weeks and tell me what you think.

And what did your wife make of your hot new underwear?

She laughed. She said, “You were on this bus one day too long, weren’t you?”