By Penny Wolfson

I’m cleaning Toby’s closet, a tangled space in the bedroom where he lived till he left to finish college. The room has violet walls, a chandelier with candelabra bulbs, and a Persian rug. On the walls hang a framed print from a Tin Tin book and a collage he made in the fourth grade, which he called “Sunset in Jail.”

I’m still referring to Toby as “he” some of the time which he says is OK, but two years ago, while we were walking on a local trail, he stopped and turned to me, all five-foot-ten of him, and said, Mom, I need to tell you something.

What could it be? Of my three children, Toby had always seemed to me the most known, transparent, accessible. In my world—as the mother of a physically disabled first son and a sometimes arms-length daughter—Toby was the one I depended on, the one who gave me undivided joy. So when he said, finally, “Mom, I’m 99 percent sure I’m a girl,” the shock was real and immediate. I felt blown away. My heart faltered, my world fell. Because I understood right then that the Toby I had known—or thought I’d known, the Toby I had helped to create, perhaps to invent—was gone.

No doubt it was a moment of liberation for him. But for me, it felt devastating. I had never suspected. I had simply thought of Toby as someone special, a gifted person who didn’t mind holding unpopular views. The fact that he played on the girls’ volleyball team in middle school and liked silk pajamas as a five-year-old did not clue me in. He had never mentioned he felt like a girl; he had never pleaded to wear female clothing; he had never had a doll. His best friend was a boy he’d known since toddlerhood. They spent all their time playing video games.

For months after the announcement, I hardly slept. I could barely write. Only blips, telegraphic phrases, burst out here and there, stingily. It seemed as though writing about it would make it so, and magically, not writing about it might make it not so. For a time I haltingly wrote fiction, as though I could see and express my thoughts only in the third person, where all my frightening fantasies—of amputation, transmogrification—could emerge without judgment. I avoided people I knew, barely able to say the words that now explained Toby, who was soon-to-be-Tobi.

For some time, I held on to the one percent Toby had said he wasn’t sure of. I thought he might change his mind. What had I done? What hadn’t I done? Wasn’t he too young to know what he wanted? These thoughts kept me up at night, filled me with furious anxiety all day.

And now I’m combing through his closet, sifting through the changes and the left-behinds, and I’m finding it sobering and sad. And illuminating. The closet—a boxy, walk-in affair—has been piled, every which way, with a jumble of stuff: video games jammed into milk cartons; toiletries, bins of Legos and matchbox cars; the shades we ordered but didn’t install because Toby wanted black-out curtains and these didn’t completely cover the light. (What was keeping him up at night? Why so hard to sleep with even a chink of light?)

Here in the closet are other costumes: men’s dress shirts, a Brooks Brothers hounds-tooth sports coat, two suits—one from Toby’s bar mitzvah, in tans and browns, with a flag of gleaming polyester for the pocket and a sleek charcoal-gray Dolce and Gabbana, with narrow trousers, bought for some high school dance. I still recall the pleasure I felt when he slipped on the tailored jacket and pants at the store. He seemed instantly beautiful, ready, I thought, with his gentle eyes and lanky build, to wow the girls. He seemed like the boyfriend I wished I had in high school.

On the bottom shelf I find the Seiko silk ties I had bought in a Madison Avenue shop for his twenty-first birthday; they are still, two years later, in their slip box, swathed in tissue paper, unopened, bearing their expensive price tags. I had sent them to Toby along with a whiskey-soaked cake to celebrate his coming of age. I saw him as I thought he was, an elegant young man for whom I could buy something expressly male. How wrong I was! Was this also the birthday for which we bought him a badger-bristle shaving brush with a dish of sandalwood soap, which I also now find now, lounging among the rejected toiletries?

In the closet I also find the newer costumes: the flowered, cotton dress, the high-heeled fabric booties, the teased and tangled wig Toby wore for a few weeks, now sitting atop a Styrofoam skull on the top shelf. There are shaping inserts for a bra “for enhanced cleavage” and a laser hair removal kit with instructions on how to “permanently disable the hair follicle.” Crammed into one corner are a bottle of strawberry-scent mist and a container of Summer’s Eve body powder, to sprinkle on your “lady places,” with a Cotton Breeze scent. When did that self arise? Where?

This is a bewildering, confused repository. But it’s the silk ties that pain me most. They were my fantasy of Toby, and they seem to lie there as stark reminders of all my love and error.

When Tobi meets us to see the play Hamilton, she is wearing a strange getup—a long-sleeved kelly-green sweater with puffed sleeves and piped edges, plus black tights. Thin tights, like pantyhose, not leggings. “When women wear that outfit they wear leggings, not tights,” I remark, and she says, “Well, people I know dress like this,” and I think maybe this is true on that live-and-let-live campus where she goes to school.

I ask about the Dolce and Gabbana suit, the one I bought for Toby as a man: Will you wear it again? And Tobi says well, possibly, now and then, and I wonder if she is still confused herself, not willing to completely cede an earlier life, those earlier costumes. She tells me she is still hanging out mostly with men, men who play video games night and day, and again, I wonder….

But I know Tobi does not wonder. She tells me so. There is a confidence in her choice for her future. And she is free in ways I never saw before—still with no partner, an ambitious career path that remains unsettled—but maybe now she sees the sunset from outside of jail.

I think of something I wrote soon after Toby revealed himself: our children are here to remind us of loss. And there is loss for me in Tobi’s revelation. But it’s only in the last few months that I have considered not only the ties that bound us together, but the ties that might have bound him, hand and foot, mind and body, to a self he rejected, which kept him from being who he was, and who she is. A self I may now be able to see more clearly.

Who cares, really, if the Seiko ties are ever worn? The ties that bind us, Toby and me, or Tobi and me, rather, are, after all, tighter and closer than gender, than any article of clothing could ever express. We are united by every nuance and joke and dinner and fight, by the embroidery of family history, by the similarity of our vision. We remain linked, as the old hymn says, by “the ties that bind/the fellowship of kindred minds,” by blood, by nature, by inheritance. And, irrevocably, by love.

Penny Wolfson is an award-winning essayist with three unusually special adult children whom she sometimes writes about. 

Like what you are reading at Motherwell? Please consider supporting us here. 

Keep up with Motherwell on Facebook, Twitter, Instagram and via our newsletter.