Drag Queen for a Day: Why This Admissions Officer Walked the Walk of Inclusion on HBO

Don’t judge a man until you’ve walked a mile in his high heels. Or until you’ve taken a few steps in them at least. If it feels uncomfortable, that’s kind of the point.

Are you with me? Because the story of Darryl W. Jones, an admissions officer who became a drag queen for a day, is the story the weary realm of higher education needs right now. The story of a guy who put himself out there — in a dress, on a stage — for the sake of others. For an important reason.

Though some admissions leaders are tight-lipped tacticians who never take a public stand, many members of the profession believe in something greater than their institution’s success. We just don’t hear them talk about it very often. And, no, we usually don’t see them wearing a big wig and sparkly gold eye shadow on national television.

It all started last summer when Jones, 57, got an unexpected phone call: HBO was coming to Gettysburg, Pa., to film a show. The cable network wanted to interview a straight ally of the local gay community, and Jones, senior associate director of admissions at Gettysburg College, fit the description.

“Why the heck not?” he told his wife.

Jones, who is black, is the college’s coordinator of multicultural admission. At first he thought the program was going to be about race, diversity, and inclusion in America. As he eventually learned, HBO was filming We’re Here, an unscripted series in which residents of small towns throughout the nation are recruited to star in a one-night-only drag show. The point is to empower local folks who are often pushed into the shadows — and to promote acceptance in their communities.

A warm, broad-shouldered fellow with a voice full of bass notes, Jones didn’t know anything about drag culture. But when asked if he would perform in the drag show, he didn’t hesitate. “If I’m asking people to think about issues of race, which are important to me,” he says, “I couldn’t be a hypocrite who wasn’t willing to walk in someone else’s shoes.”

So, on a hot day, with the cameras rolling, Jones tried on a wicked pair of black suede booties with five-inch heels.

Every town can tell a story, but Gettysburg can tell an epic tale. It’s about searing conflict, racial division, and the fragility of American ideals.

The three-day battle fought there in 1863 hastened the end of the Civil War. In his famous speech there a few months later, President Abraham Lincoln described the nation as “dedicated to the proposition that all men are created equal.”

Jones, who was born and raised in Gettysburg, always felt the truth of those words in his bones. Early on, he learned that some folks didn’t feel it in theirs.

He remembers the name of the white classmate who called him the N-word in elementary school. He remembers exactly where he was when a white kid mimicking a Southern accent said “It’s about time for you to go to your country, and I’ll go to mine.”

Then there’s a memory both bitter and sweet. At a high-school track-and-field championship, a white competitor he had just outrun muttered a racial epithet under his breath. One of Jones’s white teammates jumped in: “Don’t you ever call my friend that again. And I’m glad that he beat you.”

Jones considered himself fortunate. He grew up in a fairly diverse neighborhood. He lived in a loving, lively home where records were always spinning — the Jackson 5, Billy Joel — and someone was always cooking up something delicious.

His big, tight-knit family included several educators. Relatives told him the same thing his mother did: Don’t be shy about succeeding where others might expect you to fail (in school), or where success might seem like fulfilling a stereotype (music and sports). He thrived in all those pursuits.

Jones’s mother, who ran a social-services agency, also told him this: “You decide just to be excellent and love yourself for it.”

Many kids, though, grow up without reassuring words in their ears. Jones understood that well before he graduated from Pennsylvania State University, in 1985, with degrees in biology and psychology. He had always felt the need to serve others, but his first job out of college was at a bank on Wall Street.

While visiting home a couple months after graduating, Jones ran into Delwin K. Gustafson, then dean of admission at Gettysburg. He was known throughout his profession as a kind, genuine mentor who looked out for others. He asked Jones how work was going.

“I love the paychecks,” the young man said, “but I would love to do something else.”

The admissions office had an opening, Gustafson told him.

Jones applied for the job and got it.

Then he started asking prospective students important questions — questions about who they really were.

Finding the right dress is key. But first you’ve got to find the right theme.

During the filming of We’re Here, Jones hung out with the established drag queens who star in the show. His guide, or “drag mother,” Bob the Drag Queen, was a tall, amiable celebrity who won the eighth season of RuPaul’s hit TV show, Drag Race.

“I’m gonna be your drag daughter,” Jones tells Bob in a scene filmed for the show’s first episode, “and I want to be beauuuutiful.”

“Oh,” Bob assures him, “you’ll stun the children.”

“I’m the daughter I never was,” Jones deadpans as he and Bob share a long hug.

Though laced with light moments, We’re Here is no gag. It’s a poignant, at times painful, look at difficult relationships. There’s Hunter, a young, gay makeup artist who wants to become closer with his father. There’s Erica, a conservative Christian hoping to reconnect with her estranged daughter, who recently came out as bisexual. Like Jones, they agreed to participate in the drag show.

Along the way it was decided that Jones would wear a Civil-War-themed dress for the performance. “Because,” Bob explains in one scene, “we’re using drag as a window into what it’s like to be a person of color in Gettysburg.”

So … what is it like?

A lot better than it once was, says Jones. Some of the town’s elders attended segregated schools; the place was once known for redlining practices that harmed black families. Today, he says, Gettysburg is as “open” as any small town, though not necessarily more so. The town of 7,900 is in the center of Adams County, where President Trump won two-thirds of the vote in 2016. There are farms and more farms.

Here, remembering the Civil War is a big business. The famous battlefield is part of a national park with more than 1,300 monuments honoring Confederate and Union soldiers. In town, the Dixie flag hangs outside some stores. Shops sell T-shirts emblazoned with it. The Blue & Gray Bar and Grill serves burgers named for generals from both sides (the “Gen. Robert E. Lee,” honoring the commander of the Confederate States Army, is topped with ham, swiss, lettuce, tomato, onion, and mayo, and served on a ciabatta roll).

Jones eats there. “The burgers are good,” he says.

Mostly, he finds the town friendly. “But is it perfect? Nope.”

Neither was the fit of his drag wardrobe. In one scene from We’re Here, Jones — 6-foot-1, 245 pounds — gets fastened into a metal corset. “OK,” he says, “my pancreas just got squashed.”

Then it’s time to try on shoes. Somehow, Jones manages to shove his size-11.5 feet into the sleek black suede booties with platform heels.

But can he dance in them?

Walk in them?

Stand up?

Just because you invite someone over doesn’t mean they will feel welcome. The same is true on college campuses. Admitting an applicant is one thing. Making it affordable is another. But that still isn’t enough, Jones says, especially when it comes to underrepresented students: “Diversity is something that you have, but inclusion means that you embrace it.”

Embracing diversity means that the entire admissions staff must share responsibility for recruiting underrepresented students, for visiting public and charter schools in urban areas, Jones believes. On some campuses, those tasks largely fall to staffers of color.

“That’s apartheid recruiting,” he says.

Like many black admissions officers, Jones has known discomfort on the road. While driving to and from high schools in other cities and towns over the last 35 years, he can remember being stopped more than 10 times by police officers for no apparent reason.

That is: He’s been pulled over while driving a rental car below the speed limit, while wearing a suit and tie, while transporting nothing more remarkable than a box of Gettysburg College brochures. Each time when the officer approaches, Jones says, he shows his hands and politely asks why he was stopped.

“Just checking,” he’s been told.

When he walks into a high school, Jones tries to establish trust. To ask about the self beneath the surface. To make them feel comfortable on a campus they probably haven’t seen or can’t begin to imagine. He avoids using insider terms, like “liberal arts” or “holistic admissions,” without explaining them to students first.

In 2015 Jones visited the Young Women’s Leadership School of East Harlem. There, he met Tyra S. Riedemonn.

Riedemonn, then a junior, expected him to ask about her academic interests. Instead, he asked her this: “What are you passionate about? Do you collect anything?”

The questions made Riedemonn comfortable. She told him she was really into … makeup and lipstick. For 15 minutes they sat in the lunchroom discussing the mysteries of packaging, how cosmetics companies use advertising to appeal to various demographic groups.

A few months later, Riedemmon met Jones at a Starbucks for her official interview. They discussed her interest in theater, her family’s story. She grew up in Washington Heights, with little money. Neither her mother nor her older siblings had attended college.

For a while, Riedemonn was leaning toward a big-name private college in Pennsylvania, but she didn’t “feel the outreach” from it that she felt from Gettysburg, from the inquisitive Mr. Jones.

Ultimately, Gettysburg offered her a full ride. It was a ton of money, sure. But without a feeling of connection to the campus, the feeling that someone was invested in her success, the young black woman figures she might have seen the generous offer from a mostly white college as merely a jackpot.

“He made me feel special, wanted, and worthy of it,” she says.

So she enrolled.

Every admissions office, Jones has long believed, must have a close relationship with its office of multicultural affairs. “So that there’s a warm hand-off,” he says, “with both sides working on recruitment and retention.” For many years he has worked hard to fortify the link between those offices at Gettysburg. Long ago, he came to understand that the college must include gay, lesbian, bisexual, and transgender students in its thinking about underrepresented and potentially underserved students.

Now and then, when Riedemonn struggled in classes, she would go talk with a dean at the Intercultural Resource Center, where students could get one-on-one mentoring. “I feel like I’m sinking right now,” she would say.

Sometimes, she would walk into a classroom and see no other black or brown faces. Sometimes, she would wonder if she was too far behind other students who attended more rigorous high schools. And sometimes, she would wonder if others valued her opinions.

“Negativity can creep in,” she says.

Riedemonn says she always left the center feeling reassured, though. She felt supported — and included — at Gettysburg, by white and nonwhite students alike. And by Jones, who’s known on the campus as “Uncle Darryl.”

“He always lets students know that he’s in their corner,” she says. “If there’s one person they have, it’s him.”

Riedemonn started working in the admissions office in 2017 and never stopped. For a while she got to interview prospective students. She listened for small details, hints of what each teenager liked.

One day, Riedemonn sat down with a young woman who was visibly nervous. After hearing that the visitor was a Disney freak, she drew her out by talking about the Descendants series. After 15 minutes, she could see the high-school student’s nervousness fading.

The moment was a tribute to Jones, widely known throughout his profession as a kind, genuine mentor who looks out for others, just like the dean who hired him 35 years ago. Now, he passes something on.

Riedemonn, who will graduate in May with degrees in theater arts and cinema & media studies, is applying for jobs in her chosen field. She wants to be an admissions officer.

Jones learned a lot during his crash-course in drag culture.

For one thing, he discovered new lingo, as unfamiliar to him as the vernacular of admissions is to many prospective college students. If a drag queen is “sickening,” for instance, she will cause her audience to “gag.” (Don’t worry, both outcomes are good.)

Some insights affirmed his approach to admissions outreach. One was that not all drag queens are drag queens for the same reasons: Some do it to empower themselves, some do it to empower others, and some do it for 17 reasons.

“If you want to learn about someone, you have to ask the right questions, treat people as individuals,” Jones says. “You can’t lump all these groups together — first-gen, rural students, inner-city Latinas — and assume they have the same needs and wants.”

The first episode of We’re Here, which first aired in late April, concludes with a spirited performance at Gettysburg’s Battlefield Brew Works. Two hours of makeup and a bright yellow dress with a poofy skirt has turned Darryl Jones into a Southern belle named Darrylina of the Joneseses.

When Darrylina takes the stage — with a black parasol and ruby lips, eyes full of confidence — the big crowd shrieks its approval. She and Bob the Drag Queen do a choreographed dance while lip-syncing the words to “Free Your Mind,” En Vogue’s 1992 hit. (“Free your mind and the rest will follow/be color blind, don’t be so shallow”). The chunky gold ring on her left hand glints like a small star.

Recalling the moment months later, Jones can still feel the exhilaration of the too-bright stage, the heat of his costume, so heavy he worried he might faint.

He can feel a truth in his bones, too. “We have to be willing to trade experiences,”

Jones says, “to figure out what it’s like to be the so-called other, no matter what the other is.”

That night, Jones didn’t end up wearing the wicked black suede booties with five-inch heels — they were much too treacherous to dance in. “There was no way in the world,” he says. He wore his own dress boots instead.

But so what? Jones did his part. He stepped into the unfamiliar, embracing those who call themselves queens, just as they embraced him as one of their own. It felt good to be included.