Everyone asks Harper Steele about “the Will Ferrell diamonds.” This is what she called a pair of diamond earrings that Mr. Ferrell gave her during one of the final scenes of their documentary “Will & Harper.” The earrings were a souvenir of their westward road trip, the transient setting of the film, but more important, they were a celebration of her coming out as a trans woman.
In 2021, at the age of 59, Ms. Steele, a comedy writer and the former head writer of “Saturday Night Live,” emailed friends that she had decided to transition to live as a woman. “It’s a wonderful thing when your mind and body revolt against the unnatural, despondent thing you’ve become,” she read aloud from her letter, on-camera in the documentary. “I’m not going to be good at this. It’s really going to be slow and awkward and terrifying and joyful. Mainly I’m hoping I don’t lose anyone I care about.”
Ms. Steele stores the Will Ferrell earrings in a box for safekeeping, only wearing them for special events. “I’m afraid to lose them,” she said. And with the exception of the fake pearls she wore during a video interview — just to balance out the rest of her outfit — Ms. Steele said she won’t wear jewelry “unless it means something.”
In a conversation that’s been edited and condensed, Ms. Steele discusses the pieces that do mean something to her: her grandmother’s ring and her granny’s watch.
Talk about the cameo ring from your paternal grandmother.
My sister is sort of the vector for the feminine side of our family — I have two girls and a nonbinary kid, and I have three brothers. I associate more with the feminine side now, and I’m very happy to be a part of that side. And so my sister gave me this ring, which is my grandmother’s.
My grandmother collected cameos. It’s a dark maroon with a white figurine. I don’t think this is a very expensive thing. It’s a beautiful thing.
So my grandmother collected them when I was presenting as a young boy. She gave me a tiger eye, which was a clunky, thick, very masculine ring. And I loved that thing so much and really have never been a ring person. But I lost it. You shouldn’t give an 11-year-old kid a ring. So I hated losing that. In hindsight, I’m fairly happy I did.
And the watch is from your maternal grandmother, granny?
This is just a very plain Elgin watch. I’m sure it’s not real gold. This definitely went to my mother, and then was rescued, after my mother passed, by my sister. And my sister was just very good at welcoming me into that side of the family. So these two things represent exactly that to me.
What do these pieces mean to you?
These are very emotional to me. I’m struggling to explain what it means to be trans, and then to be welcomed home. It’s just a welcoming. I feel warm, I feel welcomed by the women in my family. I transitioned after my mother passed. Neither one of my grandmothers, they had a different idea of maybe what I was or something, but they knew me, they knew Harper Steele, and I got to spend a lot of time around with ‘em. And I’m just happy to connect with my sister, especially. I love my father, of course, and I love my brothers. What a great change of life to be able to now be a part of this other side.
Have you thought about passing down the cameo ring and the watch to your children?
I have two girls, and my sister and I probably will be the ones who pass a lot of the granny and grandmother stuff down to those two girls. I have a nonbinary kid who is more trans-masc leaning, and I have a great collection of things that come from my own world when I was presenting as a guy and things from my father. I mean, our family was not a big collector of precious things that we passed along. I got my whole mother’s jewelry case, which I can tell you came out of a drugstore.
Does the jewelry connect to something bigger for you?
Looking down at my hands now, I see something that I didn’t allow myself to have for 59 years. My hands are different. They’re now attached to the right body. Everything is in its place. And so the jewelry is a reminder of, I like to say “home,” or I’m where I’m supposed to be.
One more thing I want to just say in general about, I guess, femininity: I don’t necessarily think that all women accept me into sort of that matriarchy as a trans woman. And that doesn’t really bother me. I’m trans first and a woman second, in my mind. This is just my opinion. However, opening myself up and being vulnerable as a woman has opened me up to the female side of “S.N.L.,” of all my writing friends — love is a strong word, but love for Maya Rudolph, Tina Fey, all these people who are my friends. But it opened up a more expansive sort of love for just the female side of my entire work life, and looking back at how much women helped me to get to where I am.
So all of it ties into the superpower of being a woman, and being vulnerable, or not afraid to be vulnerable. But there’s something very special about that to me because I didn’t allow myself to have that. And so these two things are reminding me that this is the world I live in now, and it’s a better world.
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