‘it’s A Jack-off!’: Schlossberg Lookalike Contest Names New ‘people’s Princess’

There aren’t enough Jack Schlossbergs.

So far, only a few contestants have stepped forward from the crowd of hundreds here at the President James Buchanan Memorial at Meridian Hill Park.

“If no more Jacks show up,” Georgia Parolski, one of the contest organizers, says into her neon-pink bullhorn, “I’m gonna start picking people.”

She surveys the crowd, pointing her finger. “What about you in the white jacket with the yellow stripe? Do you want in? Come up here, sir!” Her co-host, Ruchika Sharma, 28, squints and points: “I see a brunette white man over there. We’re taking last-minute entries.”

The crowd hoots and hollers.

Ultimately, roughly a dozen or so young men, a baby in a backwards baseball cap hanging out in a sling with his mom and at least one self-proclaimed lesbian end up competing.

“It’s a Jack-off!” someone shouts.

We have gathered here to witness the crowning of the “People’s Princess” — “princess” being the man, woman or baby who “brings light to the darkness of political times” and looks the most like John Bouvier “Jack” Kennedy Schlossberg.

That would be the Kennedy scion, Vogue political correspondent, self-described “silly goose” and nerdy Tik Tok heartthrob with a penchant for posting goofy videos of himself, say, lip syncing to Fleetwood Mac from inside a Dunkin Donuts. Or dancing shirtless in a backwards baseball cap. Or quoting Lord Byron while skateboarding. Or laying down his dating “terms.” “I can’t handle anything less than all of you,” he tells his 436,000 followers.

Today’s event is the latest in a spate of celebrity lookalike contests cropping up around the country: In New York, it was Timothee Chalamet, who thrilled the crowd with a surprise appearance. In Chicago, it was Jeremy Allen White of The Bear. San Francisco? Dev Patel. London had Harry Styles. Now Washington has — who else? — Schlossberg.

In fact, this is as quintessentially a D.C. event as you can get. Not so much Old School, go-go loving, pre-gentrified Black D.C., but company town D.C. — albeit a much hipper company town than it was a decade or so ago. As Henry Johnson, a 28-year-old contestant puts it, “this is very D.C. You couldn’t do this anywhere else.”

The prize: $50 in cash, a $100 Zip Car certificate and one-year membership, a $100 gift card for Salazar Restaurant, bragging rights — “and maybe my number,” Parolski says into the bullhorn with a laugh. (Later, she holds up a sign that says, “I’m single.”)

All of this came about not so long ago, when Sharma, a law student at American University, had an aha moment. She texted her friend, Parolski, who works in public health research, at 3 in the morning: Why not host a celebrity doppelganger event in D.C.? The two started blasting the event on social. If you build it, they will come — and so did the corporate endorsements, along with over 1,200 RSVPs.

“We thought that D.C. needed some levity after the election,” Sharma says, “and if we could bring folks together and remind them of a silly, fun time.”

So yes, silly is precisely the point.

One by one, the contestants announce themselves. There’s Adam, clad in a white turtleneck and white eyeliner, who declares he actually didn’t come to compete: “I came here to husband shop!” There’s Jay, who says he should win because, like the Kennedy clan, he hails from Massachusetts, works in politics — and sports an abundance of chest hair. There’s Johnson, who deadpans that he should win because he also has a relative who hates vaccines. There’s Sierra Hanash, 20, a George Washington University student who says they decided to compete at the last minute.

“I’m 6’2”,” Hanash says, facetiously — they’re more like 5’2”. “And I’m proof that Jack Schlossberg is a lesbian. … I’m doing it for the girls and the gays!”

And then there’s Martin Burstein, a 23-year-old fellow with the Energy Department, who runs up on stage and begins to strip: Off comes his shirt. Then his pants. Except he can’t get them off over his shoes. So he yanks and yanks, until he stands before them clad only in the board shorts he had on underneath his pants. Then he plops a backwards baseball cap over his long sandy-blonde waves. (The cap features an eagle wearing sunglasses emblazoned with the American flag above the word, “’Merica.”)

“What’s up, y’all,” he says. “My name’s Martin. I am single, and I came here to win.”

(Spoiler alert: Burstein does not win.)

The contest, which lasts for about 30 minutes, isn’t complicated. Whoever gets the most applause makes it to the next round, which entails trivia questions: What’s Jack’s zodiac sign? (Capricorn.) Which frat was Jack in? (Sig Ep.) What Kennedy relatives were the subject of the documentary, Grey Gardens? (Big Edie and Little Edie.) Which countries did Jack’s mother, Caroline Kennedy Schlossberg, represent as U.S. Ambassador? (Japan and Australia.)

And because Schlossberg’s mom did her ambassadorial duty in Australia — and Schlossberg has posted speaking like an Australian — contestants are asked to tell the crowd a little about themselves … in an Aussie accent.

After the trivia portion, the judges huddle before narrowing the group to the final four.

Hanash, who’s made it to the final round, nods approvingly at the other competitors: “I feel good about this.”

The judges ask the crowd once again to applaud for their favorite, holding a sparkly black tiara over each of their heads. It comes to rest on Daniel Bonomo, a 25-year-old grad student studying foreign affairs at Georgetown University. He’s tall, lean, with a shock of thick black hair and a prominent nose not unlike that of Schlossberg himself.

Afterward, Bonomo says he decided to compete at the urging of his girlfriend. He took the contest seriously, studying Schlossberg’s TikToks and memorizing some of his key lines, most notably quoting Schlossberg’s romantic “terms” for an appreciative crowd: “I need you. I need you and I don’t want to live without you…”

“I’m a silly, goofy guy,” Bonomo says, looking a little shocked, standing there in his tiara. “Honestly, I wasn’t expecting to win.”

And no, he’s not looking for a career in politics. “I really want to work for the State department. I’m a civil servant.”

Notably missing from the crowd: Schlossberg himself, who’d announced on X that he would be attending. Some in the crowd, like Olivia Schwartz, a 29-year-old who works in “Dem politics” and her friend, Emma Mont, 27, who works in digital comms, don’t mind at all. They’ve been tracking Schlossberg on social media — Mont has alerts for whenever he posts — and they could tell he was still hanging in New York City this morning. “It’s just a fun bonus if he shows up,” Mont says.

But for two George Washington University students, Yael Loubat, 20, and Reva Dalmia, also 20, Schlossberg’s absence is a big, fat letdown.

“I was devastated,” Loubat says.

“I genuinely thought he was going to show up,” Dalmia says, “I didn't think it was too much of a stretch after Timothee Chalamet. … Don’t say you’ll show up and stand us up.”

Still, they remain big fans.

“He definitely did his part during the election to get the younger vote,” Loubat says. “He was active on social media, trying to get like engaged younger voters. … It’s good to inspire the younger generation.”

As for Schlossberg himself, he is last seen on Instagram posting from a car dealership, decrying Tesla batteries, which, he says, “are not better for the environment!”

“Why aren’t u at the Jack lookalike contest :((((,” a follower posts.

Posts another: “what all the ppl r wondering.”