Jennifer Finney Boylan Looks Back on Her Infamous Interview With Oprah

They were in the middle of taping The Oprah Winfrey Show when the conversation turned to surgeries. Jennifer Finney Boylan had written a memoir, She's Not There, which would go on to become a national bestseller, one of the first by a trans author, but at this point, it was 2003 and the media was still trying to figure out how to talk about the trans experience.

"She has a vagina," Oprah began to sing after Jennifer answered her question. "I kind of sat there and took it," Jennifer says. She made a joke back, but it wasn't till filming ended and she was on the plane returning home that Jennifer wished she'd said something else.

And still, Jennifer Finney Boylan's multi-episode appearance on the Oprah show helped to change the public perception and discourse around trans people. Audiences were used to seeing trans people presented on talk shows as punchlines, a man's attraction to a trans woman could only be accompanied by shame. Jennifer was a wife, a mother, a college professor who'd written a book. She felt familiar and knowable. For the majority of the population who didn't know a trans person and wasn't exposed to them on TV or film where representation was sporadic and less than favorable in 2003, seeing Jennifer on the Oprah show was a game-changer.

Jennifer talks about her interview with Oprah on this week's episode of the podcast, LGBTQ&A, as well as another groundbreaking TV moment: Laverne Cox and Carmen Carrera's interview on Katie Couric's daytime talk show where they pushed back against Katie's questions about whether their "private parts" were "different now."

She also discusses the dangers of increased visibility and why she's secretly envious of younger trans folks.

Check out highlights from the interview here, subscribe on your favorite podcast app, or listen to the full interview on the audio player below.

Jennifer Finney Boylan on Oprah asking her about surgeries:
That changed the conversation...we always talked about operations. Tell me about your operation. Have you had the operation? Where did you get your operation? Can you have an orgasm? That was the number one question that used to be asked of me every time I'd speak anywhere. Can you have an orgasm? I'm like, "Yeah, I can have an orgasm. Can you write a book?"

A key moment for me was when Carmen Carrera and Laverne Cox were on the Katie Couric show and they said, "We're not going to go there." I wish that I had the courage to do that with Oprah because Oprah asked me that question and I was like, "Yes, I have a vagina." And Oprah began singing to me.

Check the tape. She sang, "Yes, she has a vagina," and I sat there.

She sang that and I said, "Actually what you mean to say is, yes, we have no bananas." So, I made a little joke back to her and I kind of sat there and took it, but later, I remember I was on the plane going home thinking, "That's not cool to say that." Then, there was no sense of anybody pushing back and I guess I was not courageous enough to push back. Also, I was a little intimidated by Oprah, so I didn't do that.

But later, Carmen and Laverne did and that was a huge moment and now people know that when you have a transgender person on your TV show or whatever, that that's not what the conversation is going to be about.

On writing for a non-trans audience:
She's Not There is not the most radical book you're going to read in the trans canon. ...A lot of my writing is not aimed primarily to a trans audience or even at a queer audience. It was aimed at my mother's bridge club. It was aimed at moms who are concerned, moms who are maybe uncomfortable with talking about LGBTQ issues, but who want to do well by their children and who are moved by the story of someone who seems familiar.

After I was on that first Oprah show, somebody emailed me. I remember she was from Omaha, Nebraska. She said, "Jenny Boylan, the weird thing about you is that you seem almost like a person somebody could know."

To me, that's an amazing phrase because that's the thing right there. I think we used to think of transgender people as...it wasn't somebody that you could know, somebody next door.

And now I'm hoping, not only as a result of my work, but of the work of many people who are now living their lives openly and joyfully, now there's a lot of people that you could know that are trans, and who are trans not the way I'm trans but the way that they are trans, and that all these different ways of being trans are cool.

[Related: Jennifer Finney Boylan writes about how having a transgender parent affected her kids.]

On dangers that come with increased visibility:
With increased visibility also comes increased blowback, increased resistance, and in some cases, increased violence and legislation against us by people who used to give us a pass because they didn't know that they were supposed to hate us because they didn't know we existed.

I'm sorry that the blowback generally doesn't fall upon me, on white ladies of privilege from New England. The blowback falls upon people of color and women of color in particular in the transgender community.

Not only, but particularly people who are doing sex work. Some people who want to do sex work and other people who have to because that's the only way to keep the lights on while you're trying to get from where you are to where you want to be. And it costs a lot of people their lives.

On not being interested in debating her humanity:
You know what my counter is? My counter is, Look at me. Look at my life. You want to know how I refute you? I refute you by living every day according to what's in my heart and according to the stars by which I pilot my boat and I'm not here to have an argument about my own humanity. I'm not here to even participate in an argument about my humanity, which I might actually win or lose, right?

I mean, I'm happy to talk about all this stuff, obviously. It's interesting, but nobody should have to take part in a conversation in which their sense of self is something that they have to defend, and that's whether you're nonbinary or binary or mortal or immortal. People should get to be themselves, period.

On being envious of the younger trans people:
I've never really talked about this before. I guess in some ways...I mean I was glad to be able to be a person who helped change the culture and bring us to this place, but in another way, I feel like, how cool would it be to be in the next generation? To be in the generation where things are not quite so hard, where when you came out, you didn't have to explain everything like you just invented the whole thing yourself.

So when I say, "The shire has been saved but not for me," there might be a little creeping self-pity, which is perhaps uncalled for because really, I am one of the luckiest people that I know.

On her evolving view on what it means to be a woman:
I've been maybe three or four different women at this point in my life. Early on in transition, I was very youthful. I cared a lot about my appearance and being sexy and my clothes. Fashion was really important to me, passing was really important to me. Appearing cis, I'm sorry to say, was probably more important to me than it should have been. And then I was a soccer mom and I don't know what I am now. I'm like an older stateswoman, maybe.

When you go through transition, for me, when I had clothes in my closet that I wanted, it was such a huge thing. I couldn't believe, "Oh my god, there's dresses. Look at all the dresses." Well, I don't wear dresses anymore actually, except for graduation or something.

At one time in my life was, the symbol of all that I had dreamed and hoped for and had been kept away from me, has now become, "Oh, that." That old thing; I should give that away. It's the spectacular mystery of life, the way we keep becoming other versions of ourselves.

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