When I Was 16 I Won a Drag Show in Florence

I was on my way to a party when I got the notification. It was a trans-women-only party, my first, hosted by my electrologist in her small Chelsea apartment.

She’d invited me every month since I started beard removal that past October. It was now February. I desperately wanted to meet other trans women, but I thought of her apartment as a place of pain. Electrolysis is, after all, the process of hot needles and tweezers removing every single hair follicle one by one. I didn’t want to voluntarily enter this space when I didn’t have an appointment. Or at least that’s what I told myself.

I really just wanted to postpone taking a chance on my only known resource for community. Because once I went, and my worst fears came true, once I realized I didn’t fit in, all hope would be lost. October I said I’d go in November. November I said I’d go and then just didn’t show up. December I had the excuse of traveling for the holidays. I don’t remember what I said in January.

Walking from the subway, after almost an hour on the train from Queens, I cursed myself for not going in the fall. With Christmas season long past, spring still so far, February is always the coldest month in New York even when it isn’t actually the coldest. So when my Kesha-heavy playlist was interrupted with a ding, I fought my addiction an entire half a block. Then, caving to the impulse, I sucked my glove off and bent my hand into my coat pocket only to find the worst notification.

“On this day…” A FaceBook memory. No ego boost of a like or a follow. No potential of a comment. Usually just a reminder that three years ago I was a man even though turns out I didn’t have to be.

I sighed and swiped up. My glove was already off, and, also, I hate myself. But my screen didn’t reveal a man. Or a boy. Or an embarrassing status. There was a girl, a model, walking towards the camera.

It was me.

I stopped a block away from my electrologist’s apartment to look closer. I realized the pink skirt was made of tissue paper, the silver shoes were tin foil, the top was garbage bags, and on the garbage top were cone breasts made out of gold foil. The outfit was silly, but it worked. And my makeup, my posture, my stare, those really worked.

The picture was posted on a friend’s account, a FaceBook friend, not a real friend. #TBT Abbey Road Programs’ Next Top Model. A memory of a memory. This hadn’t happened in February. It happened seven months prior, July 2010.

When I was 16. When I won a drag show in Florence.

I didn’t know I was trans until I was 23, less than a year before this party, less than six months before I started on hormones, less than two and a half years ago to this very day. There were clues, sure, especially in the few years leading up to my coming out, but none of the main signifiers. I didn’t steal my sister’s clothes as a child. I didn’t enter puberty filled with horror.

I have explanations, excuses I used to state aggressively, desperate to defend my newfound discovery. Now I couldn’t care less how convincing someone finds them. I didn’t steal my sister’s clothes because I was a rule follower; stealing and cross-dressing were wrong. I didn’t detest puberty because I was so behind developmentally that my body changing felt like hope, like possible normalcy. These explanations make sense to me whether or not they make sense to you.

I didn’t know I was trans because I didn’t know anyone was trans. All I had was The Silence of the Lambs and an episode of The Oprah Winfrey Show where she asked a trans woman why she couldn’t just keep her penis. The trans woman asked Oprah if she’d be okay having a penis and my mother turned off the TV in disgust.

I spent the first months of my transition mining my past for clues, trying to find as much evidence as possible before coming out to doctors, my parents, and the rest of the world. Everyone always thought I was gay. I always cared deeply about queer culture, community, and activism. I always connected more with girls and women. I really loved Fun Home. Oh yeah, and I always fantasized about having a woman’s body and spent my whole life wishing I was born a girl. Turns out cis men don’t feel that way.

It’s a strange experience to have no idea that trans women exist, and, also, to know you aren’t one of them. I lacked the language, but gender nonconformity will find you even in the suburbs. When I came out to my mom, she told me that at four years old I was disturbed by my friend’s “brother” who wore dresses. She shared this as proof I wasn’t trans, but it’s actually an explanation for why it took me so long to come out. My awareness that being trans is wrong pre-dates my earliest memories.

When I learned the word transgender, when trans people started appearing on TV and on magazine covers, I assumed this was about other people. The stories that cis society latched onto were so limited, so binary. They were easy to ignore.

Trans women are women. I just wanted to be one. That was the difference. The language used to convince cis people that being trans is not a choice, convinced me that transitioning wasn’t a choice I could make.

I’d failed to meet the narrative requirements.

Instead, I’d spent my childhood and adolescence trying to be a boy. I wasn’t very good at it, but I tried really, really hard. I didn’t wear bright colors, I didn’t listen to pop music, I didn’t even style my hair until I was 17. I certainly wasn’t the kind of person to dress in drag.

And yet I was. And yet I did.

Abbey Road Programs is a series of arts-forward study abroad trips for high schoolers. I think I found them by googling “high school study abroad programs get me the fuck out of this suburb.” It would be the first time I ever left the country, and the longest I’d ever been away from home.

Florence wasn’t my first choice. But their Paris program required a fluency in French that I did not have. Florence was an obvious second. This was all based on what cultures I longed for most while making my way through the Criterion Collection. That’s another way of saying it was based on which mid-century actresses I most wanted to be with and be.

But I did not set off to Florence with hopes of meeting an Italian girl. No, my heart remained back in California with my first love, my close friend, my first kiss. I told everyone on my trip that I had a girlfriend and I thought this was true. We had kissed. Twice. And we said I love you. Sure, they said they were too old for me. Sure, they actively encouraged me to date other people. Details.

My misguided monogamy was especially unfortunate considering the program that summer was 43 girls and 8 guys. When I brought this up, the bro-iest guy on the trip smiled and said, “It’s an arts trip. That’s the secret. Girls love art.”

It’s true. We do.

My “girlfriend” “broke up with me” on the last day of my trip via Facebook messenger and I immediately regretted the missed opportunities. But it was actually one of the best decisions I ever made. Up until this point my entire life had been controlled by crushes – all of my female friends, the ones I actually crushed on and the ones I didn’t, I framed as crushes. As a boy this was what I was taught. When you like a “girl” (some turned out not to be girls) it’s because you want to date her, or, more crudely, to fuck her. Simple friendship was not assumed. Envy was definitely not assumed.

But on this trip I was quickly isolated from the boys and accepted by the girls. I won’t say I didn’t have crushes. I now know exactly who I had crushes on and whether those crushes were romantic or envious or both. But at the time I pushed those feelings away. And, as a result, I just became one of the girls.

My closest friends were roommates. Their room number was 14-2 which I’ll remember until the day I die. Their names in the script I wrote based on this summer are Maya, Ali, and Jess. I had art history with Maya and Ali. Our professor took us from museum to church to museum giving us the greatest art tour of Florence one could ever imagine. I had film with Jess and went on a different sort of tour of Italy within the confines of an apartment turned theatre. During the day we absorbed art and at night we enjoyed our first experience of freedom. Sure, we had a curfew, but until then we could wander around, doing anything we wanted. It was thrilling.

I reconnected with Ali when I was first working on the script and asked if it had been weird for her that I was a boy. Why did they think I wanted to hang out with them instead of the guys? She shrugged. The possibility of me being gay did cross her mind, but mostly it was normal. She had guy friends back home. What was monumental to me hadn’t even phased her.

But it was monumental. Being away from home and in a new environment allowed me to reinvent myself as it often does. And being surrounded by girls guided that reinvention in ways I didn’t expect. It was the closest I came to being myself until I was 22. And I had no idea that had happened. I pushed that month away. Or reframed it, around the art, around the “breakup.” It’s correct to say that I’ve always been a girl. But the truth is that month was the first time I was actually a girl.

This would all come back with the photo. Suddenly, I remembered the month as it had really happened.

When I rediscovered the photo in February of 2018, Call Me By Your Name and Lady Bird had just lost the Academy Award for Best Picture. But you wouldn’t know that talking to my friends.

Guillermo del Toro’s fish-fucking fairytale may have won the statue, but all Twitter could talk about was whether Armie Hammer should’ve eaten the peach and the moment when Lucas Hedges is singing Sondheim and Saoirse Ronan puts her hand on her chest.

While Call Me By Your Name left me a bit cold (an opinion very unpopular among friends), I more than made up for it with my love of Greta Gerwig’s debut. I saw the movie two weeks after starting hormones, two hours before seeing my parents for the first time since coming out to them over the phone. My second adolescence had begun.

My love of the movie rose from my present identification with Lady Bird’s stubborn spirit, and my nostalgic identification with her wish to flee California for New York. She was me now, she was me then, she was me.

And also she wasn’t. Because paired with this fervent love was an overwhelming awareness of how little of me was actually on screen. How many blonde cis girls in swimming pools could I possibly identify with before facing our deep end of difference? How can I accept my past, reckon with it, love it, if I’m constantly comparing it to a truth that hardly exists for anyone and definitely didn’t exist for me?

I began thinking constantly about what Lady Bird might be like if it was loosely based on my life instead of Gerwig’s. I wondered what the queer fluidity of Call Me By Your Name would be like as a trans story instead of just a gay one. I questioned whether it was even possible. How do you tell a coming-of-age story about a trans girl who had absolutely no idea she was trans?

And then I saw the photo.

The entire time I was at the trans woman party my mind raced with memories, scenes, plot points, and characters. On the train home I typed them up furiously on my phone. And over the next seven months I crafted them into a 140-page script.

As the hormones settled into my body, as breasts grew and hips developed, as the hair on my head thickened and the hair on my body thinned, I lived in that summer in Florence. Within the pockets of my day job, my relationship, and my efforts to suddenly be a woman, I wrote and wrote and rewrote and wrote. The way I work is constantly rewriting while writing, so by the time I finished a first draft it was actually more like a fifth. And that completed first draft had changed so much, combining characters, dropping truths, inventing truths, and ultimately creating something like fiction that I now struggle to separate from what really occurred.

I wrote three more drafts before leaving New York, cutting dozens of pages, adding a dozen back. November 2018 I held a reading in the apartment I shared with my girlfriend at the time. It was casual; no one was the age of the characters they played. Instead I filled the cast with actors I’d met during my six and a half years in New York. People who mostly didn’t know each other, but who meant something to me.

I didn’t realize it was my going away party.

Two weeks later I moved to LA for a temporary job that became another temporary job that became a decision. I broke up with my girlfriend, left behind my friends (and my electrologist), and reached a sort of conclusion to my second adolescence.

The reading went well. As I played the Vivek Shraya song that ends the movie, I was filled with emotion I suppressed because no one wants to be the girl who cries at the thing she, herself, wrote. But I felt like I’d done it. I’d written an adolescence like mine. There’s no high drama; it’s European in style as well as setting. But it works. In the reading, it worked.

A note I’ve received from people who have read the script since is nothing happens. Another note I’ve received is the suggestion that he comes out at the end.

But she doesn’t. There are signs throughout. The audience knows she’s trans. She will be played by a trans actress. But the character never knows. Just like I never knew. I refuse to change that.

There’s only a small moment, a hint, an almost.

There’s only a moment when she’s her true self.

It’s when she wins the drag show.

It happened the last weekend of the trip. The scheduled activity was “Abbey Road’s Next Top Model.” (Other last weekend activities included a talent show and a cooking contest.) It wasn’t supposed to be a drag show.

The idea was we’d split into eight teams and had to create outfits using supplies we’d been given, a mix of household goods and random arts and craft materials. But then someone realized: eight teams, eight boys, the boys should be the models.

Some of the boys scoffed at this idea, performing the mandatory masculinity. Other boys celebrated, not taking it seriously, but relishing the attention and class clown opportunities.

I stayed silent.

I didn’t want this to happen; I desperately wanted this to happen. I did not want this to happen. And then it did.

I was lucky enough to have someone on my team who aspired to be a costume designer. She quickly assessed the materials and her eyes zeroed in on a pair of cones. A concept developed. I’m not sure how this teen in 2010 was so familiar with Madonna, but she decided to create a cone bra and I was certainly not going to stop her from giving me a chest.

She made everything: the blonde head piece, the black garbage bag top, the pink skirt which she gave volume with a string of air-filled bags underneath. The aluminum foil jewelry, the aluminum foil shoes.

While she made the clothes, one of the other girls did my makeup. This wasn’t the anemic stage makeup I’d donned for the school plays; this was high-femme glam. I was beautiful.

Everyone else walked out to “California Gurls,” Florence’s song of the summer. But when it was my turn we placed a request.

I made it through the wilderness
Somehow I made it through
Didn’t know how lost I was
Until I found you

I walked forward with poise and precision. I walked like a girl. I walked like myself.

The laughter that had met the other boys died away with me. People cheered. They genuinely cheered. The only laughter was a laughter of shock at how good I looked. I looked so good. I felt so good.

I reached the end of the “runway” and I spun around tearing off my big, pink skirt. A reveal. Underneath I had a tight aluminum-foil miniskirt, carefully crafted to highlight my legs.

Now everyone cheered. I blew a kiss to the crowd and I smiled.

Like a virgin
Touched for the very first time

I don’t know if I’ll ever film my fictionalized version of this event. I don’t know if my movie will ever get made. I hope so. If I’m being dramatic, which sometimes I feel like being, I’d tell you it’s the reason I was put on this Earth. I have a lot of dream projects, but it’s the only one that feels so personal I know that no one else will ever make it, or, possibly, anything like it. This movie might be the only chance I’ll get to see my coming-of-age story on screen. It might be the only chance other trans women who share something like my experience have as well. I hope not. I’d much rather be the third than the first.

Sometimes I feel the desire to make it so badly. It’s something like desperation. Like filtering my experiences through fiction is the only way to make them real. Like making these experiences real is the only way to prove I’m a person.

But, I guess, in a sense it’s done. The story has been written and it’s come alive in my mind. It was read aloud in a room of twelve people I love. And they got to experience something like what I imagine. It would be nice to share the story with more people, to take the specific images bursting around my brain and project them onto a screen. But for now this will have to do.

When I was 16 I won a drag show in Florence.

And when I was 24 I wrote about it.🗺️

Edited by rachel.

The Travel Issue [button: See Entire Issue]

Drew is an LA-based writer, filmmaker, and theatremaker. She is currently working on a short film about Gordo from Lizzie McGuire’s transition (it’s canon) and a million other projects. She also runs social media for I Heart Female Directors. Find her on Twitter and Instagram @draw_gregory.

Drew has written 44 articles for us.

26 Comments

    • Most of the cast would be unknown queer teens! It’s really important to me that the lead be a trans girl even if she’ll be a “boy” the whole time.

      But yes I, of course, have a very-2010 dream soundtrack I’m happy to share:

      1. 5 Years Time – Noah and the Whale
      2. Lover I Don’t Have to Love – Bright Eyes
      3. California Gurls – Katy Perry feat. Snoop Dogg
      4. Home – Edward Sharpe & The Magnetic Zeros
      5. Blah Blah Blah – Kesha feat. 3OH!3
      6. Like a Virgin – Madonna
      7. DJ Got Us Fallin’ in Love – Usher feat. Pittbull
      8. Like a G6 – Far East Movement feat. The Cataracs & DEV
      9. According to You – Orianthi
      10. My First Kiss – 3OH!3 feat. Kesha
      11. Ridin’ Solo – Jason Derulo
      12. Brick by Boring Brick – Paramore
      13. All I Do is Win – DJ Khaled feat. T-Pain, Ludacris, Snoop Dogg & Rick Ross
      14. Girl, It’s Your Time – Vivek Shraya & Queer Songbook Orchestra

      • hmmm better check with scarjo first JUST TO BE SAFE

        Casting unknown queer kids is def the way to go. There needs to be so many more opportunities for them.
        I have to admit i was not plugged into pop music at the time and don’t know any of those songs except Like A G6, which my boyfriend at the time got kinda obsessed with, specifically a dubstep remix of it. Oh, and Like A Virgin, of course. A song from my own era. Curious fact? I went to the same high school as Madonna, and had some of the same teachers. Curious apocryphal fact? Madonna offered to pay for our school’s new auditorium, which we badly needed, if the school board would display a gilded nude statue of Madonna somewhere on the school grounds. This would have been around ’90/’91 or so. The board was clearly unimpressed and the auditorium never got built, no idea what happened to the statue.

  1. Hey Drew, great story of a part of your life. I love that your experience doesn’t fit a neat narrative that is all about convincing others about who you are. Seeing the pic of you at the end was a real surprise and delight. Thank you.

  2. Such a beautiful piece! Thank you so so much for sharing it.

    Also I think this thought is something that I’d love to read more on – and to an extent I think applies to all the bits of LGBTQ –

    “The language used to convince cis people that being trans is not a choice, convinced me that transitioning wasn’t a choice I could make.

    I’d failed to meet the narrative requirements”.

    • I definitely agree that applies to many of us!

      I have another piece I’m working on that gets more specific about my personal coming out, but I would also like to see something more widespread across identities/cultures/experiences that explores this.

  3. I wanted the right amount of quiet to read this, and this morning was ideal. This is phenomenal. This is archaeology of a life at its finest.

    Layers and layers painstakingly brushed away. The way you play with time. First you live your life, then you re-live your life, then you re-fashion your life, then you re-create it for us, then it gets born again in the minds of all who read this, exponentially. Augh ! Fantastic.

  4. Congratulations on that win, in more ways than one!
    Love this essay and I am sure your script would make a way a better movie than „Call Me By Your Name“ (which I also wasn’t overly fond of.)
    Coming out as trans always reminds me of that moment in „The Neverending Story“ where Atreju faces the mirror, and is let through, because he does not hide anything from himself. He is a hero in that way, and a rare one at that.
    Whoever comes out as trans or genderqueer or whatever, always is that kind of hero to me, because this necessitates having looked into the mirror and coming out victorious. Maybe not unscathed or glorious or unmessy, but nonetheless heroic.
    Because most people will not dare look. Only few even will dare accept the knowledge offered by the mirror and less even, the consequences.
    Maybe this says more about me and my own complicated beef with gender, but maybe who we are is, in fact, a Neverending story, and also, maybe life itself is full of quirks and irony, and you winning a drag show while unknowingly being in drag all day,every day, is well, one of those twists. Especially set against the back drop of that ridiculously gorgeous city.

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