I hated makeup in high school, but not on me, on the women I knew. I hated the black mascara and eyeliner that rimmed the lids of a girlfriend, who confessed often about how ugly she felt—how she felt like shit without her makeup on. I suppose, now, that other cosmetics might have been subtly on her face in a way a fifteen-year-old boy couldn’t detect. I told her how beautiful she was, with or without the makeup, and she loved me saying so. I was hurt when the makeup stayed on regardless of what I said. A teenage boy can think he can dissolve his girlfriend’s body issues by saying she was beautiful.

She was one of so many girlfriends and girl friends who didn’t like their bodies and faces. Makeup seemed more sinister to me with every blink in their black-rimmed eyes: The expensive creams and cakes whose function seemed only to tell every pretty girl in my life they were ugly. I shut my eyes at the makeup aisles in grocery stores, wearing extra-large T-shirts and hoodies that I, too, used to cover parts of my body I couldn’t bear.

I learned how to put on makeup nearly four years ago, when I dressed for Halloween as the Queen of Hearts. A sympathetic old friend took me to purchase mascara, eyeliner, and a bright shade of ruby lipstick universally referred to by the makeup girls in my high school drama department as “Ho red.” The old friend walked me through application in my Portland bathroom and said, “Makeup is an art, not a science.”

The eyeliner I used rarely after that, and the lipstick even more rarely, but the mascara tube’s exercise has become ever more regular, a slow uptick over months and years, and now I put it and some foundation on more or less every day. The latter I learned to apply because of a somewhat teenage problem.

“Mikayla,” I yelled, clutching my phone on the sidewalk. “I need your help.” “What’s wrong?” “I have this enormous fucking hickey on my neck and there’s this reading I’m going to tonight and everyone I know will be there and fuck, I’ve gotta rid of it.”

She laughed. “Okay. Hey, sugar? You’re going to be fine. Go get a cheap thing of foundation and call me back.” She told me how to dull it with a frozen spoon, and how to use a quarter to push the blood around, but the way she taught me how to apply the foundation worked the best.

Last weekend on the subway, I was studying a picture of a famous woman’s face on my phone. Her black eye makeup tapered to a point far beyond the outside of her eye, the bottom and tops of her lids shaded thick. Her cheeks were airbrushed smooth, the skin looking almost pulled over her face. Bionic. That makeup-hating clear-eye-loving high school boy, I thought, would’ve scorned this picture, wishing women could celebrate their pure, natural bodies.

I’ve been wondering lately what that boy would think of me, squinting at the mirror and rubbing brown cream into my face. I started putting on foundation just to cover my upper lip, where a feisty inch of mustache shadow has survived decimation by lasers and electrolysis. Hiding a mustache seems prudent, but I started, slowly, to rub it on the rest of my face too. Tricky often says to me, “You have such nice skin! You don’t need to put on as much as the rest of us,” and her saying this does make me feel pretty, and despite this (like those girls from high school?) I still put the stuff on anyway.

After the lip comes the tiny flecks and splotches on my cheeks raised by self-scrutiny, and then my entire face goes, and while I like the blank smoothness I can never seem to cover up everything that didn’t used to bother me.

Before I transitioned, I sometimes talked about seeing women on the street, that mental clothesline of desire of having a female body—a sensation I’ve referred to a couple times here as “Ah! Shit!” moments. And many responded, friends, family, or therapists: “Well, I think that’s a feeling most women experience.” They said this whether they were supportive or unsupportive, but what I understood less were the supportive ones, who said this as if it confirmed my womanhood.

The difference between a troubled boy and a troubled girl saying “I wish I could look like her.” There are weak, self-doubting days when that line doesn’t feel like much of one. Transitioning has made me start to love my body in a way I hadn’t previously let myself think about, but there’s also a slow-drip of ways I’ve started to dislike it, too. My impossibly lanky arms. The incessant frizz of my hair. The stubborn bulge of a belly I’ve every reason to be happy with after six months of its reduction through working out and estrogen-fueled fat redistribution. The miniscule flecks and splotches on my cheeks to be covered.

But for all the doubt encapsulated in a circle of foundation, I absolutely love mascara. I love the brightness it adds to the face. I love that it takes a most unassuming and subtle body part, the eyelash, and makes it vibrant. I love it on others and I love it on me. The clear-eye-loving high school boy might’ve liked it too, if he’d known himself a little better.

My junior year of high school, I went to class in full drag. My friend Naomi had suggested I do it—she loved dressing up boys as girls and we went to a sleepily average school chronically in need of some shock. I said yes with more enthusiasm than I really understood. Naomi gave me clothes and another friend, Angela, put on elaborate, drag queen-y makeup. Fever red cheeks, forest-green eyeshadow, the curliest of mascara jobs. Angela was a painter, and in the subsequent months as I watched her paint I saw the bright intensity on her face was the same as that when she worked brushes onto mine.

It was an eventful day, but my memory always narrows to a short drive I took alone during lunch, singing and steering my stepfather’s blue Chevrolet Celebrity past my former middle school when I had a swift vision of myself as female. I was driving that car and wearing those clothes and singing that song as a sixteen-year-old girl. I saw her as if I was just behind her, gazing at her five feet behind the trunk.

Her hair was straight, down to her neck. I couldn’t see her face, or what she was wearing, just her straight hair, her head moving slightly while she sang, tooling down Gilham Road in the blue Celebrity. She seemed so correct, so right. It was like swallowing a bolt of electricity. Almost immediately it was gone, gone before I passed the middle school and drove over the Beltline overpass, three years before I could admit that I no longer wanted to be a boy.

It’s undeniable that the “Ah! Shit” moments have become less about gender dysphoria and more “I wish my belly was as flat as hers” or “I wish my shoulders were as narrow as hers,” and I think this whether it’s women on the street or on the subway or on a billboard.

I do believe, in the end, that there’s a difference between a girl wanting to look like an ideal she’s been given, and a boy wanting something completely different from what he’s been given. The farther in transition I go, I feel more of the former and less of the latter. But when I’m in front of the mirror, fixing my wild, frizzy hair, when I’m wrestling and cajoling and threatening it with straighteners and blow dryers and clear slimy product, I think of the girl in the car. I see her and that straight hair so clearly. I know, eight years later, that the woman I’m trying to be is her.