Is it 2025, or 2001? It’s hard to tell looking at the line of Gen-Z women lined up outside faux dive bar Ray’s on a cold Tuesday evening in a clash of winter coats and cowboy boots. Tonight’s dress code is laser-specific (the Sex and the City Saddle Ranch episode) and the urban cowgirls are here with one mission in mind: dominating cutthroat rounds of pop-culture trivia.
This is the house that Natalie Shine — a 27-year-old fashion influencer and game-show host, looking very Carrie Bradshaw in a 2003 fringed pink satin Dolce & Gabbana corset — built. In February 2024, Shine hosted the first Big Silly Trivia game from her Los Angeles apartment. She’d texted friends about a Zoom quiz; seven joined, including her mom. She wrote the questions and played the part of host. “I was a theater kid,” she tells me, and quickly realized, “Whoa, I’m pretty good at whatever this wacky new thing is.” Fans agree. The attendee list has since swelled to more than 10,000, mostly by word of mouth. Over the past year, she’s hosted in-person games at Jean’s, Casetta, and the Roxy Cinema in New York. In September, Shine launched The Big Silly Talk Show, where she dissects the latest pop-culture news in a set resembling Lizzie McGuire’s bedroom. Last month, Malala Yousafzai made a guest appearance at a game titled “Mall Madness!” Shine likens the show’s growth to puberty. “It feels like a transition from being this scrappy kid to entering the big leagues.”
Shine is the evening’s (appropriately named) host.
Each Wednesday, thousands receive a text that begins, “HI DOLL!” They log onto a password-protected, pastel-pink site straight out of a 2001 iMac. Shine, a relentlessly upbeat host, appears onscreen, transforming the familiar quizmaster trope into something more like an archival designer-dripped emcee. Over the next 30 minutes, attendees open an app called Kahoot and answer questions like “In Princess Diaries 2: The Royal Engagement, which activity do the princesses participate in?” (mattress surfing) and “What object did Trisha Paytas break on her opening night of Beetlejuice?” (a chair).
Tickets for tonight’s event sold out in hours, with more than 300 people on the waitlist. Rather than charging attendees a ticket fee, Shine (who studied marketing in school) and her husband and co-founder, Emmett Shine, turned the hobby into a business by pitching brand partnerships, sponsored rounds and ad segments, and occasional merch drops; brands like Gorjana, Lisa Says Gah, Le Creuset, and Glow Recipe have all sponsored prizes. In addition, Shine estimates that she’s awarded over $20,000 worth of prizes including Bottega Veneta wallets, Mane tools, and Marc Jacobs purses.
But more than the prizes, the game’s draw is Shine herself, who describes her role as “Merv Griffin meets Carrie Bradshaw.” Fashion, pop culture, and preteen nostalgia shape her questions. Shine dresses the part each time, too: She appeared as Elle Woods on a college-movies-themed episode with glasses perched on her nose; as Drew Barrymore in Scream, blonde-bob wig and all, for a “Blondes in Spooky Movies” segment; and as Abraham Lincoln on a Halloween-special talk show, beard wig included, with comedian Joe Hegyes as Mary Todd. “Campiness is key,” she says. Some of her favorite looks on the show include a Jenna Rink–inspired Versace dress and an archival pink Chanel suit.
-
The big, silly crowd puts its nostalgia to the test.
-
-
-
Shine minds the leaderboard.
/ 4
As she does every night, Shine starts by leading the crowd in the Big Silly pledge. Its last line goes: “I promise to be myself, to be kind to others, and always stay silly.” An animated intro plays on a projector while she croons the lyrics into a mic. She fires off questions like, “What did Carrie bring Mr. Big when he returned from Paris?” (McDonald’s) and “Meadow Lane, the Tribeca gourmet grocer, is inspired by which upscale market?” (Dean & DeLuca). The young women — and a few men — tap responses onto their phones, squealing when the check mark appears. A cluster of backbenchers dressed more punk than their fellow “Saddle Ranch” attendees linger by the pool table, projecting indifference while still dutifully punching answers into the app. On the other side of the room, what appears to be the boyfriends-and-husbands table slumps in quiet resignation.
Shine, who attended college during the peak of the pandemic, says part of her mission is to help young women who feel isolated find a “third space.” And historically, trivia nights have skewed male — think tables of dudes sparring over the Super Bowl or Civil War history. Big Silly Triva wants to change that. “Women age 18 to 35 are some of the largest groups of casual gamers,” she said. “I thought, How do you reward women for their day-to-day interests?” Trivia made sense. It’s universally understood, adaptable to any topic or cultural moment, and leaves room for comedy. “It’s like those memes about dissociating while someone explains board-game rules,” Shine said. “I’m one of those people.”
She remembers the first time someone stopped her on the street to say their roommate had won a prize the week before. Now, at least a dozen women in that friend group play each week. “It’s fun because when I ask what everyone got up to that week, girls will share that they got their Ph.D., got engaged, or got their dream job.” Playing Big Silly Trivia is part of their routine — no major life event could push it off their weekly schedule.
Among them is 26-year-old law student Molly Recker, who said she and her friends struggled to meet during the school year but now see each other weekly at BST. “It’s cool to connect with other young women in the city and bond over trivia topics you normally wouldn’t see at a bar because they’re considered too feminine or niche,” she said.
Margaret Wong, a 37-year-old strategy and operations specialist in San Francisco, said she’s hardly missed a game, even logging on from a hotel room in Positano and a boarding gate at SFO. “Winning is always fun,” she said, “but we also support each other during harder times, like when someone’s dealing with a sick family member.”
Winner, winner, Marc Jacobs purse dinner.
As the game wraps, Shine hands winners their prizes: custom BST x Ray’s T-shirts, Ray-Ban x Meta sunglasses, and a black Marc Jacobs Cristina purse I found myself coveting. I cursed myself for not playing — too many times I mouthed answers at the projector. I convinced myself I was almost Gen Z. I had free-fallen into the Sillyverse. I understood why so many do — and it didn’t feel so silly after all. Knowing each American Doll by name, the year Lindsay Lohan’s second mugshot dropped, or each Miss Dior campaign headliner might seem redundant to some, but to others, it’s invaluable cultural intel that brings us together.
As for what’s next, Shine has her eyes on live TV. She cites Sabrina Carpenter’s A Nonsense Christmas as inspiration. “The call is coming,” she said. “I’m open to wherever it leads.”
Click here to preview your posts with PRO themes ››
