While living in the Sugar Hill neighborhood, she made the rounds, auditioning for television, recording hip-hop tracks, free-styling with the Roots and D.J.ing at the Apollo. To make ends meet, she was a waitress at the Sugar Shack and a hostess at the Odeon; she was fired from Heartland Brewery.
She once tried to book Ginny’s for “Mo’ Betta Wu,” a cabaret show she produced that reinterpreted Wu-Tang songs as jazz standards. The club turned her down. “Remember when you were begging them to let you on here,” she said to herself. Now the club wouldn’t work for her anymore. “It would fill up too fast,” she said with pride.
Harlem itself has also changed. She was amazed by what she called “the next-level Whole Foods” on West 125th Street. Still, this trip to Harlem wasn’t as traumatic as the one she took last year, when she’d gone to get some West Indian food from a favorite place and found a Papa John’s instead.
As she walked south on Malcolm X, she could see the apartment of a friend, the actor Brandon Victor Dixon. She remembered how, more than a decade ago when she booked a gig as a V.J. on MTV2, he’d said to her, “You’re about to blow up.” She did, but it took a while. (She texted Mr. Dixon, who is appearing as Aaron Burr in “Hamilton,” and asked to meet up. Mr. Dixon texted back: “Onstage woman.”)
Ms. Seales landed the “Insecure” role after meeting Issa Rae, the series’ creator, via Twitter. The casting directors initially asked Ms. Seales to audition for the role of Tasha, a foxy bank teller, but Ms. Seales knew this wasn’t for her. “I don’t have the proportions for ‘hood hot,’” she said. So Ms. Rae asked her to read for another role, Tiffany.
Tiffany is smart, sociable, a little princessy. And the role called for a 30-something Ivy League graduate. “Oh you mean, my actual life?” Ms. Seales said, though she prefers sparkly kicks to glass slippers.
A block away, she arrived at Harlem Shake, a retro-themed diner, where she ordered truffle fries. Harlem Shake divides its wine into three categories: Cheap, Good, Bourgie. “You know which one Tiffany would choose,” Ms. Seales said, before sticking with a watermelon cooler.
Ms. Seales has forceful opinions about race, class and gender, and she isn’t shy about expressing them on Twitter, in her comedy, over fries. A recent viral moment: confronting Caitlyn Jenner about racism during a dinner party livestreamed on Katy Perry’s YouTube channel in June. “This country is here for you,” she told Ms. Jenner. “This country ain’t here for me in the same way, sis.”
During that charged conversation, Ms. Seales kept herself calm by digging her nails into her palm while she spoke. She knew that being seen as “another angry black woman,” she said, might devalue the message.
As she moved to an outdoor table at Harlem Shake, Ms. Seales was feeling anything but angry. She smiled when a vintage Mustang rolled past. “I love cars,” she said. “I’m a nerd.” Other enthusiasms: “Star Wars” (She has a Jedi tattoo and a cat named Lando Catrissian), “Star Trek,” “Lord of the Rings” and “Harry Potter.”
Ms. Seales wears her nerdiness proudly. She has a master’s degree from Columbia University’s Institute for Research in African-American Studies and goes full fangirl on black academics. She is pitching a game show, “Smart Funny & Black,” which tests contestants on their knowledge of black history and culture. She’s also busy with her stand-up, sketch writing, an autobiographical YouTube show (“Get Your Life”) and an advice series for Harper’s Bazaar”(“Gem Droppin’”) — not to mention her new status as a regular on “Insecure.”
“Tiffany is probably who I would have turned out to be if I got famous at 21, so it’s fun to play this alternate-universe version of me,” she said.
Back in the real world, Ms. Seales looked out past the tables toward the sidewalks and the people and the buildings. They seemed small to her, she said, almost like a toy model.
Ms. Seales thought about it for a moment while she speared a fry. “Part of the reason why I’m looking at Harlem so weird is because I’m not stuck,” she said. “At one point it felt like I was stuck. And now? No.”