What I Learned Being a Drag Queen for a Day

I am thinking about grading papers while Kendra, a drag queen, surveys my eyebrows. I have bushy eyebrows — brown caterpillars. Home to a pride of lions. Canoes. Kendra debates with her friend, another drag queen, about whether or not flattening them with a glue stick would open up some more real estate. I want to say no but don’t. I am in her world now.

Back in the dressing area/history classroom, my students dart around with handfuls of makeup and eyelash extensions, asking no one in particular if they need anything. My principal is struggling with the zipper on his sparkly-green Fred Flintstone number. A history teacher asks about wigs and whether or not we have enough time to track down a wig shop for more.

Kendra rolls my fishnet-wig-cap over my eyes to help stencil the glitter. “Flatten your eyes as much as you can.” I have no idea what she means. She swishes her blue hair over her shoulder: “Sorry if this hurts.”

Outside of a few schools in California, Indianapolis’s Shortridge High School is the only public high school in the country to host a drag show. This past May, as a teacher of freshmen English at the high school, I agreed to let my students dress me up to help raise money for Brothers United, an organization that helps prevent AIDS and STDs within the gender and sexual minorities of Indianapolis. I said yes, then promptly forgot about it.

The drag show came about when history teacher Alene Smith thought it would be a great way for the two clubs she sponsors — the National Organization for Women (NOW) and the Gay-Straight Alliance (GSA) — to end the school year. The two clubs saw an opportunity to create a more inclusive environment for Shortridge’s LGBTQI+ community — a community rarely considered or celebrated in schools. So, once a year in May, teachers, and students get dressed in drag and put on a show in the school’s own Caleb Mills Auditorium.

This year, the show raised over $500 for Brothers United. Even though the money definitely helps, Terrell Parker, interim executive director of the organization, says, “Brothers United is extremely honored that a school not only chose to give to our organization but chose to help empower marginalized people of color within the LGBTQI+ community.”

Thirty minutes to go before the opening number, Alene Smith walks in with four pink boxes of wigs under her arm. “Oh, my god, you would make a great blonde,” Kendra says pointing at me with the eyeliner pencil that had been dug into my eyes five minutes earlier.

I was paranoid about saying something stupid around Kendra and all of my students. I have a knack for saying things without thinking. I even went so far as to have two students paint “THINK BEFORE YOU SPEAK” in my old classroom as more of a reminder to me than my freshmen. I had already messed up when brainstorming what my queen name should be, suggesting ‘homophone’ to another teacher, who just shook her head and told me to try again.

Kendra started her drag career fifteen months ago. There is a small hierarchy in the drag queen community, Kendra dutifully explained to me. When queens start out, they are called “baby queens” and only when they start getting paid for their acts do they earn the title of a drag queen. We talked about her past while she was blotting a bronze foundation on my face. When she was in high school there were only three gay kids in her entire school (that she knew about), and tonight she felt weird being in a high school dressed as she was — in a skintight black dress, toad green tights covering her legs with a fishnet midriff, gut pushing through the mesh, with the phrase “real love” running up and down the sides.

I told her how, when I was in high school, I was the boy who called other kids fag, gay, or homo. Kendra smiled and asked if I had gone to a small, rural high school. I had. “Oh yeah,” she starts in a motherly way, “those types of schools were the worst for gay kids. Everyone tight-knit and anyone who was different was seen as the enemy. If anyone didn’t fit the mold of normal, then they were ostracized or worse.” She was absolutely right, and I immediately felt this molten shame bubble in my stomach. It might have been the pizza battling with a nervous gut, but more likely it was from the terrible realization of who I was in high school.

Kendra says I am ready to pop on my platinum wig with the stern bangs. I rub the sleep from my legs and the soreness out of my back, then lean forward to have the coarse postiche planted on my dome. My heels are black with a modest rise — two inches. I do a nervous walk around the hallway, which doesn’t help anything — especially my confidence, which took a hit when talking to Kendra.

My dress is one of those silky magenta deals with a band of sparkles under where my tits should be. Not quite a spaghetti strap, closer to fettuccine. It’s hot. Literally. I’m already broiling and wishing I had a fireplace bellows to get some airflow going to my nether region. My feet are pouring sweat into Goodwill heels, and I am quickly feeling like I’m hungover in a heat wave — oozing out a syrup rather than sweat. I need fresh air and water.

Kendra packs her gear up and heads out with the other queen, Eva, to a show at a bar on the south side. She snaps a picture of the two of us, checks her handiwork one more time, then leaves, her words still rattling around my head.

The kings and queens are gathered backstage. The student president of the GSA gives us the set list and order of songs. I go fifth. The first number will be all of us dancing to the Rocky Horror Picture Show’s “Time Warp.” Only one of the kings knows there is a dance to the song. Alene hops on the microphone and welcomes us onto the stage.

The music starts, and we all rock back and forth looking anxiously at one another. Salsa Valentino, a king who was four hours earlier a Spanish teacher named Linda, takes center stage and begins dancing to the beat. Everyone follows suit. A lot of the crowd are my students, and they are laughing and snapping pictures of their English teacher. The crowd was told not to post pictures to social media in order to keep potential flak from outsiders to a minimum. I try my best to dance without breaking my ankles. The song ends, and we all wait backstage to be introduced for our solos. I sit on the cold tile floor with my dress hiked up to my thighs with my hand billowing some much-needed air up north.

Alene calls me up for my number. “Ladies and gentlemen, give it up for Reading Rainbow!” I walk out with my arms stretched out like I’m posturing for a fight, a grimace on my face because a part of my face looks like Grimace the purple McDonald’s monster. My principal, another English teacher, and a science teacher are my backup dancers. My song is “Filthy Gorgeous” by the Scissor Sisters, and I am getting into it — following the beat and transmediating each lyric into wild gesticulations before headbanging to the chorus. But it stops. Abruptly. The DJ is a senior who misread my timestamps and cut the song after only forty seconds. I walk off stage to an applause that sounds like question marks.

After the show I hang out with the audience, taking photos and cracking jokes, asking students if they need a date to prom in a gruff voice, before kicking off my heels and heading to my classroom to change. I peel off my dress and put my teacher clothes back on; all that was left to do was scrub the makeup off my face. I thought about leaving it on to meet my wife and friends out for a drink, but even the thought of it terrified me.

I spent the whole evening learning what it took to become a drag queen. The patience, skill, creativity, and literal thick skin one needs to get through rubbing a shading pencil over a closed eyeball for forty minutes. Kendra told me how weird it was to be in a school dressed as she was, but she did it anyway because she knew what it meant to those kids to see someone be proud of who they are. I, on the other hand, while scrubbing everything that Kendra had done for me during the past two hours, learned that I do not have what it takes to walk a mile in her heels.

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Michael Olowek

Michael Olowek

Michael Olowek’s writing has appeared in IndyStar, Another Chicago Magazine, and Sport Literate. He teaches high school English and enjoys writing.