The Night I Became a Drag Queen—and Changed My Attitudes to LGBT Pride

For a few hours on Thursday night, I looked really fucking beautiful.

I have to say it: I was stunning. It was undeniable. I was so beautiful, in fact, that it was traumatizing, even a little bit horrifying. I never expected to look like this. Truthfully, I actively didn’t want to. But there I was, looking so goddamn pretty, and loving it. Well, hating it, too. Hating it a lot, really, but still confident in the fact that I was more gorgeous than I have ever been in my entire life.

Only it wasn’t me. It wasn’t real. And it wasn’t how I ever wanted to be seen or thought of. I’m so glad I looked so beautiful on Thursday night. What I’m working on is being proud of it.

Meet Anita Help. Anita Help is a drag queen who was born and died in the same four-hour span at the James Hotel in New York City’s Nomad neighborhood.

Her purple hair is in a half pony that drapes over shoulders, matching the kaleidoscope of lavender in her smokey eye, a masterpiece of eye makeup so cool and glam-goth dramatic you wouldn’t be surprised if it turned into a butterfly, flew right off her face, and went out the back to chain-smoke hand-rolled cigarettes.

She lived her life in the spirit that she was created, which is fabulously, with love, and with enough lip gloss to make out for hours and not have to reapply before hitting the club. When it came time for her to walk the runway, she was living: feeling her face, feeling her hair, feeling her strut. Then it was time for Anita Help to say goodbye. Her time on this earth was a brief experiment, and a joyous, wonderful one. But it was one that wouldn’t be happening again.

Anita Help was a product of an event called Love & Lipliner. It was a fabulous, inspirational, inclusive event in which fans of drag, beauty, and the “drag illusion” could participate in mini makeup tutorials, mingle with some of New York City’s biggest drag queens, and a few people could receive full drag makeovers from those queens. The idea of the event was to celebrate World Pride and the 50th anniversary of the Stonewall Riots, raising money for the Stonewall Community Foundation.

That is how I found myself spending three full hours in a makeup chair being transformed into a drag queen.

I very much did not want to do this. I am also a pushover who likes attention and free drinks, so I said yes anyway. The entire process shocked me, though nothing more than my reaction to it.

What started as a silly story pitch about “Wouldn’t it be funny if I got a drag makeover?!” evolved over the three hours into something strange and more meaningful: What it takes to be a drag queen.

It’s not just makeup, hair, a brassy sense of humor, and nice fake breasts. There’s something much deeper and more profound. I never found it in myself, and truthfully might not ever. But I discovered more pride than I ever expected in those who do.

Soon after arriving at the James, I met Jan Sport, the drag queen who would be turning me into a beautiful lady.

She was so kind and tender, repeatedly fussing over whether I was doing OK, even though I was the one actively making her job harder. I kept nervously fidgeting my leg and bumping her, when she already had to spend three hours squatting and hunching over in order to make me over. I would have quit with a backache after 12 minutes.

And then there was the time she had to put eyeliner on my bottom eyelids. Fucking hell, guys. Did you know that people put eyeliner, like, inside their eyelid? This is masochistic and outrageous. It also makes your eye look 400 times more beautiful than it did before, so I’m sold. Poor Jan Sport had to talk me through this part like a child, and she was so patient, bless her.

I’m the kind of person who can’t put in his own eye drops. My boyfriend has to hold me down, pry my eyes open Clockwork Orange-style, and do the countdown trick that doctors use on toddlers to give them shots, pricking them on “two” instead of “three.”

I think when we started dating, he thought this was a cute bit, because we both love the scene in Friends where Monica has to do the same thing to Rachel because Rachel is being a wimp. But six years later and untold levels of exasperation over drops wasted because I blinked before the solution hit my eye, he is more than convinced it’s not.

What I’m saying is poor Jan Sport never stood a chance. Miraculously, she pulled it off. And, my god, did my eyes pop. They popped! I never thought I’d have eyes that popped!

Three hours is a lot of time to spend four inches from a stranger’s face as they study every pore of your own, analyzing its shape and its oddities and busily making your eyebrows disappear with a waxy cover-up paste. (“This is what we call the Uncle Fester phase.”) It is both hilarious and upsetting to see yourself with a base layer of pale foundation and no eyebrows, so rather than giggle nervously, Jan Sport and I chatted. A lot. I really like her.

I learned that she started doing drag two-and-a-half years ago. She’s a musical theatre major and did a cruise contract on a Royal Caribbean ship that ported in Dubai. It was illegal to “you know, exist as myself there,” she told me, so her girlfriends would go and buy her makeup to play around with back on board. One of them noticed that she looked a little bit like Kris Jenner when she put on makeup. Around the same time, she had just seen the episode of Keeping Up With the Kardashians where Jenner talks about wanting to join the Broadway cast of Chicago, and made a whole bit about it.

A Kris Jenner drag queen origin story? Jan Sport and I were soulmates. As for her name: “I was drunk at a McDonald’s and saw a Jansport backpack.” Honestly, it might have been true love.

In the drag community, there are drag families, in which an experienced performer, a drag mother, will mentor and help break into the industry a younger performer, a drag daughter.

Jan Sport met RuPaul’s Drag Race alum Alexis Michelle after serving together as judges for a competition that Jan had won the year before. She told Alexis the Kris Jenner story. If you’ve seen Drag Race, you know that one of the greatest moments in the show’s history is when Alexis plays Jenner in a Kardashian-inspired musical. The connection sealed their bond: Jan was now Alexis’s drag daughter.

Alexis was also at the Love & Lipliner event Thursday performing a makeover. Throughout the night, she’d pop over to see how Jan and I were doing. “Just checking in on the family.” She called me her granddaughter. It was adorable.

Jan talks to me about all the ways Alexis has helped her, guiding her through her early years in the community and helping her land gigs. She shares with me the makeup tips she learned from her, including how to better blend the contouring on your nose and a special trick with highlighter. My nose looked very thin and my cheeks literally glistened. Granny Alexis knows her stuff!

Each step of the makeover process blew my mind. The way the purple eyeshadow instantly feminized my face. How a metric ton of lipliner and gloss turned me into Lisa Rinna in a matter of minutes. How each layer and step in the process transformed my face differently, up until the final element—fake lashes the size of bat wings—that morphed me over once again, one last time.

Three hours is a lot of time to spend staring at yourself in the mirror, even for a vain person like myself. More, it is an incredibly strange experience to spend all that time in front of a mirror and not recognize the reflection looking back. And in truth, being afraid of the face you’re seeing.

Drag, cross-dressing, gender fluidity: it’s always something I outright rejected, in the way that gay men still internalize homophobia and express it sometimes quite viciously in their community. I never walked around in my mom’s heels. I never had a desire to do drag. I never had an inclination to wear makeup, or go to a Provincetown tea dance, or anything like that.

Don’t get me wrong, I love that stuff. I love the art of drag, going to drag shows, watching RuPaul’s Drag Race. Those queens are fabulous. Billy Porter, Keiynan Lonsdale, Nico Tortorella, and all the men and gender fluid people they’ve inspired with their fashion are heroes to me. And I love it when my gay friends post photos from Fire Island strutting around in their pumps and wigs. I’m comfortable around all this, celebrate it, and encourage it. But I never, ever wanted to do it.

Insecurity is a bitch, people. Shame is maybe even more ferocious.

Part of why I said yes to this is because, this Pride Month, especially, I wanted to obtain some greater grasp on who I am as a member of this LGBTQ community. What parts of my identity am I actually proud of? What still needs work? What is, sadly, hopeless? I’m getting older, and living in New York, being a member of a media in which abs, jawlines, and youth are inescapable, I’ve been grappling with a sort of existential identity crisis.

This is perhaps entirely boring to you. I agree! Who would give a shit about anyone else’s “journey”—I want to self-flagellate just for using that insufferable word—besides the person on it?

Except maybe you should care. Sharing our stories is the only way to move forward. It’s how any of us will ever feel normal about who we are. That much of Pride Month, at the very least, I understand.

Don’t get me wrong, I realize these words are being typed from a rainbow tower, where I work as a pop culture writer, where my exuberant coverage of LGBTQ issues is embraced, and an undercurrent of unabashed horniness is allowed to make its way into pieces without editors blinking an eye.

I realize I think these thoughts while waking up next to my handsome boyfriend each morning, a byproduct of a family who had a reckoning with their entire faith because of my identity, a father who traded weekends coaching my brother’s baseball team and building sets for my production of Seven Brides for Seven Brothers, and a mother who watched endless hours of Designing Women with me. I am so lucky.

But there is still so much about my identity that I harbor resentment over.

I resent that coming out is a thing I had to do. I resent that being gay is a “thing,” and will always be a thing, even to people who “don’t care”—because having to articulate that thought is still a thing. I remember the bullying from when I was younger. I remember the insults. I remember not wanting to look, talk, or act the way I did, because I hated that this was happening.

This is not a call for sympathy, not by a long shot, and not when there are so many other members of my community who are fighting for their lives. But it is candor, for whatever that’s worth.

Masculinity and normativity and passing and coding are things that I—and I would venture many gay men—have spent a lifetime thinking about, and constantly. But talking about those things also suggests some sort of femininity, because it means talking about feelings and insecurity.

So many brave queer people respond to this by being unapologetically themselves. But, still, in 2019, being yourself, especially if you’re LGBTQ, is a political act. It’s not normal, or mundane—something I’ve always wanted to be.

So that was my own reckoning this Pride Month, reflecting a new kind of shame: the realization that this is how I felt.

There’s a quote from Stonewall patron Michael Levine, who was at the riots, that I’ve been thinking about a lot, especially in light of the Love & Lipliner event: “The drag queens, they are the ones who said to the police, ‘We are not leaving.’ And they formed a chorus line outside, in front of the bar. And they stood there, dancing in the streets.”

I am not imagining myself as any kind of equal of the queens at Stonewall. My god, could you imagine? How idiotic, me, drunk off vodka sodas in the ballroom of a hotel where there’s an actual gallery in the lobby in homage to the riots. This was silly fun, full-stop.

But it was an occasion to put into perspective how far we’ve come to be there, and how far we have to go. The Uber driver insulting the drag queen standing outside the hotel as he dropped me off, for one, was a reminder of that. My own personal feelings about putting on the drag makeup and being tortured over how it would feel is certainly another.

The thing is, I did look beautiful. I did kind of hate looking like that, and I hate that I felt that way. But I looked gorgeous, and in a small way, that was healing.

Everyone at work knew that I did this, and the next day, after seeing the photos, they all had the same question: How long did it take to remove the makeup? The truth is that it wasn’t that bad. I burned through about 20 makeup removal wipes and in about 10 minutes had returned my face a messy, emo—but recognizable—version of myself.

Errant wig glue in my hair, eyebrow makeup, and especially the eyeliner were stubborn and required extra scrubbing when I got home. (There was still some residual eyeliner the next morning. Residual eye pop!) Mostly, though, it wasn’t arduous, though the rapid disappearance of Anita was a little jarring. I was just really exhausted.

What it takes for anyone to do drag or wear a dress in public or be seen in a way that radically magnificent requires a fortitude that I do not have, though I now have these fantastic portraits to remind myself that it was there, at least in some regard, at some point. More than that, though, the photos will be a reminder of the necessity to be proud, and proud of everything, of all of you.

It’s amazing what a little purple eyeshadow can do.