JFB op/ed in New York Times: “Oprah, I Hardly Knew You.”

THERE I was, on Oprah Winfrey’s couch, when she turned to me and asked: “So. You have a vagina?”

As a transgender woman, I’d gotten this question before. I allowed as how I did.

Ms. Winfrey began to sing to me. “Yes, she has a vagina.”

I interrupted her. “What you mean,” I said, “is, yes, we have no bananas.’”

Everyone screamed. Ms. Winfrey said, “We’ll be right back.”

During that commercial break, as my interviewer was swarmed by her producers and directors, I got my first good look at her. The strange thing was that at such close range, she didn’t look anything like Oprah Winfrey at all.

I’ve been on the program, the last episode of which ran on Wednesday, three times since then. Now whenever I go somewhere to speak about gender issues — whether it’s the National Press Club, Harvard, the Judiciary Committee of the Maine Legislature — I find that there’s one question I’m asked more frequently than any other.

“What is Oprah really like?”

It’s asked by earnest moms in book groups, by excited teenagers, by literary critics who disdainfully claim never to have owned a television. Once, a stoner in a bar asked me that, then said, with considerable melancholy, “Dude, it should totally have been me who got to give everybody a car!”

I never know how to answer. Like a lot of authors, I had some anxiety about going on her program. There was the very likely possibility that I would make a colossal fool of myself. More urgently, I feared that transgender issues would be treated sensationally, as is all too often the case on daytime television.

I needn’t have worried. Ms. Winfrey treated me with respect and that first show made a brief and unlikely best seller out of my tragicomic memoir, “She’s Not There,” about changing genders and keeping my family — my wife and our two sons — together. The day the episode was broadcast, my book went from about No. 300,000 on Amazon to No. 8.

Ms. Winfrey may not have hailed me as the next Tolstoy on that show (plus Tolstoy never had to allow people to film him putting on his pantyhose) but her endorsement helped people see that transgender Americans are human too. One viewer wrote to say, “The strangest thing about you, Jenny, is that, sitting there next to Oprah, you seemed almost like a person somebody could know.”

Not all of my appearances went as well as the first. The last time, the episode was titled “Oprah’s Most Memorable Guests.” They included Ted Haggard and his wife; the husband of the woman who drowned their children; an 800-pound man who’d dieted himself down to 500; a mother with no arms and legs; and a previously recorded segment featuring the Texas polygamist wives. My sons had wanted to be on as well (we Skyped in from our living room) to show that children of transgender people can turn out to be perfectly well adjusted, and as this parade wheeled by, the younger one turned to me and whispered, “I thought you said she liked us?”

What could I tell him, except, “I know. I’m sorry. I thought so too”? (My older son only had questions about the polygamist wives. “If you’re going to have 12 wives, shouldn’t, like,one of them be hot?”)

I was left feeling unsettled. Oprah Winfrey has donated hundreds of millions of dollars to charity, started a school, entertained millions and helped to change the perceptions of gay, lesbian and transgender people in this country from marginal to mainstream. But at least some of her power has come from episodes like the one my sons and I shared with Ted Haggard.

Looking back, though, how could I be anything but grateful for my time as her guest? Last year, a trans woman stopped me as I was walking up Seventh Avenue in Manhattan, and told me that my appearance on the show literally saved her life.

“But can I ask you something, Jenny?” the stranger said, after she’d finished hugging me and wiping away her tears. “What’s Oprah really like?”

What could I say? “She’s nice.”

As a guest, I felt that Ms. Winfrey was a very smart, inscrutable performer. It was only when I watched the show at home, safe in my living room, that I felt again that she was a woman I’d turn to for friendship and advice. She generates a sense of intimacy, to be sure — but you can really appreciate it only from a distance.

After that first show, she paused with me backstage for a photograph. It was the first time all day I’d seen her off camera. “We did good today,” she said, and she put her arm around me.

Later, when the photo was delivered to my house, I looked at the two of us standing there. With all that stage makeup on, I hardly recognized myself. But the woman to my right? That could only have been Oprah Winfrey.

Jennifer Finney Boylan, a professor of English at Colby College, is the author, most recently, of “Falcon Quinn and the Crimson Vapor.”

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  1. Dar
    Posted June 6, 2011 at 12:43 pm | Permalink

    For sure the woman did some good in the world and probably will continue to do so…but I have winced at many a thing I’ve seen her say on her show (or arrange). The vagina question would have been one of those. And the cast of characters who shared the most memorable list with you.

    Your observation of her as a performer…a person with whom intimacy is only possible at a distance…is facinating.

  2. Dianne
    Posted March 22, 2012 at 10:04 am | Permalink

    If I ever meet Oprah or Barbara Walters I promise I will wistfully ask, “What’s Jenny Boylan really like?”

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  • The Boylan Family, summer 2010

    DSC_0063 "You hang around our family, you learn all kinds of stuff."
  • Will Forte as Jennifer Finney Boylan on “Saturday Night Live”

    WiFo-Jennifer Finney Boylan-1
  • Jenny with Barbara Walters, December, 2008

  • Jenny atop Maine’s Mount Katahdin

    2036947979_34bfbec240 August, 2002.
  • Surrounded

    boylanWith President Clinton and Maine's Governor John Baldacci, fall 2006.
  • JFB and Edward Albee


    Edward had been my teacher at Johns Hopkins in the winter of 1986. He visited Colby in fall, 2007. As we took our leave of each other, he kissed me on both cheeks and said, "We have done well. You and I."

  • Jenny and her teacher, the great John Barth


    Jack was my professor at JHU when I did my thesis, back in the day. After many years, I can now confidently say I finally understand his definition of plot. Which is, of course, "the perturbation of an unstable homeostatic system and its catastrophic restoration to a new and complexified equilibrium."