On Orlando and Transitions

Meditations on Transgender Humans

A couple of years ago, the social media posts of “Sam,” a young gay man in his 30s, the beloved former student of a late teacher friend of mine, began shifting from a fun social and work life to marking a life in transition. First, Sam shared multiple moves, the most alarming (to me) was a move (for work) to a dangerously bigoted Southern state, where he was determined to make a go, build a community, and change hearts and minds. As life there, despite his best efforts, became less and less tolerable, he found himself in transit yet again, back to a major city in his home state. Shortly after this move, about which he detailed his joyful creation of a new home with the help of many friends, he began including pictures of himself in “feminine” clothes and accessories (pictures that reminded me of Tom Wilkinson’s character in the landmark film Normal.) Not long after, Sam formally announced that he was beginning a formal transition from “male” (assigned at birth) to “female,” which Sam said was the gender he had always felt he was. What has followed includes his documenting phases of this journey, including legal name and gender changes on his/her/their identification cards, photo records of a shift from pants to dresses and in a face in full makeup, the results of their hormone treatments, and most recently and significantly, a diary of their gender reassignment surgery, their plastic surgery to make their face more feminine, and the post-op difficulties that are part of the process.

For my own part, as an advocate and ally of the LGBTQ+ community, I have found watching this process overall to be troubling. Because I haven’t understand the source of my feelings, and because I still don’t know how best to be supportive in an honest way, I made a decision not to “heart” Sam’s posts, but instead to follow them at a distance, as it were, while working on myself to get a handle on what “transgender” means and how best to understand my muddled response to it.

The start of my own encounters with this cultural shift began by seeing cabaret. One of my favorite live performers in New York is Justin Vivian Bond, who as Justin Bond made a name in the downtown cabaret scene (and later, on Broadway, where I first saw them) in the character of singer Kiki DuRane in the duo Kiki and Herb, with Kenny Mellman as the always supportive Herb on piano. When Bond made a decision to present as female and then transition (with hormone treatments, but forgoing gender reassignment surgery), I remember items in New York magazines taking the famously cross-dressing Bond to task, saying, “Vivian? Now you’re going too far,” that sort of thing. Mr. Bond became Mx. Bond, doubled down on their activism, and used music and humor to include the story of transition into their act. “Am I he, she? I don’t know what I am,” Mx. Viv said at Joe’s Pub one night during a tribute to Judy Collins, who was there to introduce Bond and their band; Judy had used feminine pronouns, asking, “Am I using the right ones?” and in response, Viv (who presents tipsy as part of the act) said he/she/they didn’t really care either way. At the time, the idea of changing pronouns was a fairly recent idea, and we were all on shaky ground. Why not acknowledge that?

As a society, we have all been, in fact, transitioning to a new, amorphous world where gender isn’t rigid. In response to this change I think (no doubt subconsciously), expectant parents began staging “gender reveal” parties, as if to say, “My child will know exactly who he, or she, is,” which we know now may or may not be the case. And sure, as with any movement, some kids may declare themselves to be other than the gender their genitals indicate, but the truth is nothing about gender fluidity is new. For example, as a child ca. 1920, and for at least two years until she was 14, actress Katharine Hepburn insisted that the family call her “Jimmy,” and she wore boys’ clothes and had her hair cut short. Her family just went along, and why not? But there is a darker side to this, too, because her older brother Tom (who wasn’t “manly” enough, some biographers have suggested, for Hepburn’s father) committed suicide at age 16; young Kath found him hanging in a closet. As a family, the Hepburns never spoke of it again. And I can’t help thinking that while a daughter, still, can present as a tomboy, there is, still, no society space for a young boy to present as a girl for a while, try that out; let alone for either to transition.

What was troubling me about Sam’s transition had to do with a vague feeling, and I mean to be honest here, of repulsion toward the idea. Why? Why was I feeling this? Did I not quite believe him, suspect he was being exhibitionistic to be, say, a sensational social media influencer? It crossed my mind. But I don’t think he’s lying. The problem was with me, and I decided I had to understand—what I could easily accept in Mx. Viv, I struggled with in Sam, I realized, because Sam is someone I have actually known since he was a teenager. My internal conflict was much closer to what the parents and friends of trans youth might feel than I at first acknowledged. All this is really to do with gender as a societal construct, which (I see now), I’d had the good luck never to have to worry about.

The first novel I read that centered gender is Virginia Woolf’s Orlando: A Biography, which I decided to reread. Because I read with a pencil in hand, having conversations with my books, I see this must be my 6^th reading of the full novel. (The only time I didn’t record impressions was in rereading it prior to studying in London in 2000, where I went three days ahead of classes so I might haunt Bloomsbury.) Each reading had a different purpose or at least caused me to come away with distinct, and distinctly limited, impressions. First, I was wowed by Woolf’s imagination—so different from that stultifying attempt to read To the Lighthouse in college; later, the more I learned about Woolf’s life, I was charmed by how her novel parodied her father’s profession as editor and writer of the Dictionary of National Biography in England. But more profoundly, Woolf’s novel was a deep reimagining of the life of her lover, for a brief period, and dear friend Vita Sackville-West. I’ve read the novel, then, over 30 years and with many discoveries, but this was the first time I read it with an intention: while I’d enjoyed the fantasy element of Orlando changing from a man to a woman over some 350 years, up the “present moment,” aged 36 in 1928, I had never thought about this gender change more than intellectually. Yes, we see what it’s like to be a woman vs. a man over time, and that somehow Orlando having had female lovers is still okay by the novel’s end, which is quite an achievement in modernism. But what am I missing?

Books become different because we become different readers, which is why rereading is so important. This particular revisiting was prompted by a movie. Back in the early winter I went to Film Forum here in New York to see Orlando: My Political Biography, a documentary in which several trans people were interviewed about their encounters with this novel, how it became their identity bible, how it helped them survive. Because I had no personal reason to connect with the novel on that level, I’d never read it that way (and these readers needed none of the backstory of Woolf and West to find the novel both revolutionary and comforting).

But now I had Sam and Mx. Viv (as well as my friend’s grandchild, now completing middle school as a boy); I’d seen the latest in a series of American horror stories, this the story of a nonbinary student in Oklahoma beaten to death in a high school restroom by (gender-assigned) girls, the student’s head smashed in over and over and over against the floor. Where does this hatred, this viciousness, come from? Where is all this fear coming from? Could reading Orlando again help me figure something out?

Woolf’s novel was (as Nigel Nicolson, the younger son of Vita Sackville-West, said) obviously a “love letter” to Virginia’s friend Vita, who when her father died learned she could not inherit the family estate Knole because she was a woman; so the famous estate went to her second cousin Edward (who had had nothing to do with the place unlike Vita, who’d loved and cared for it and kept it running all her life), who in turn sold it to the National Trust. Vita was bereft. In addition, Vita was bisexual, married to another bisexual, Harold Nicolson, and lived her life more or less as a man in her independence. Hers was quite a complicated life story in any era, but especially in 1928, when the book was published. Woolf’s novel was a spectacular best seller.

One might well ask, How did Woolf get away with it? In her infinite genius, she went full-on fantasy, beginning Orlando’s life back in time, when Queen Elizabeth I gifted Knole (fictionalized in the novel) to Thomas Sackville, Vita’s ancestor, and when Orlando (of the title) was a boy of 16. By taking Orlando through the ages—via the voice of a biographer-narrator who confesses to being as mystified as the reader at the changes, saying simply, “but that is what happened, what can I do”—Woolf subverts the gender transition though time transition. Readers are kept off balance through humorous descriptions of the awkwardness of the gender transition, exploring the mores and their differences for men and women through the ages. Orlando embraces, finally, her many selves, her genders, over all the centuries, coming to the present moment as a poet, a wife, a mother, a woman in the 20^th Century.

The novel, as a note to those of you enticed (I hope) to read it, is not without ugliness—casual bigotry and acceptance of colonialism shockingly run throughout—which shows that no author, however enlightened in many areas, can be expected to be enlightened in all areas. But as Woolf’s biographer-narrator might say, “Difficult though this is, it’s what happened, and so we must record it.”

I must say, this journey of the past few years has been deeply affecting. I had never really thought about being a cisgender woman attracted to men since birth; I’ve had to ask myself if I was ever attracted to women, and yes, I have been—but only once I remember, as it happened oddly, suddenly, and then the feeling passed, in the audience of a theater maybe 15 years ago. I was in perimenopause at that time, I think, increasing in testosterone—was that it? Who knows? But it was real. Why did it hit me as something wrong? Why must anyone be tormented for having healthy sexual feelings, loving feelings, for our fellow beings; for wanting to express what is inside us in honest ways? Why do we continue to insist on gender reveals, coming outs? I used to wear dresses as well as pants; now I wear exclusively pants. I began dressing as a man, I guess, but with scarves and jewelry; and as a woman in America I can do this. Why can’t anyone of any gender simply discover and express themselves honestly?

“When this happened, Orlando heaved a sigh of relief, lit a cigarette, and puffed for a minute or two in silence. Then she called hesitatingly, as if the person she wanted might not be there, ‘Orlando?’ For if there are (at a venture) seventy-six different times all ticking in the mind at once, how many different people are there not— Heaven help us all having lodgment at one time or another in the human spirit? Some say two thousand and fifty-two. So that it is the most usual thing in the world for a person to say, directly they are alone, Orlando? (if that is one’s name) meaning by that, Come, come! I’m sick to death of this particular self. I want another.”
~ Orlando, page 308 (HBJ edition)

And this is where I am in this moment, today, the 10^th of March in the year 2024, writer, artist, editor, daughter, sister, friend, woman. What about you?

Love, in all its forms,

Miss O’