Debby Ryan is lost in New York. Specifically, we’ve gotten off on the wrong floor of her hotel, and are now in some sub-basement location in search of our way back to the lobby. “This feels like Fringe,” she laughs. It’s a niche reference—that sort-of-successful sci-fi show with Pacey from Dawson’s Creek?—but when you consider the actress’s résumé, it makes sense.

Ryan, now 25, has been a mainstay on your television since 2006, when she first appeared on Cole and Dylan Sprouse’s spin-off series, The Suite Life on Deck. Since then, she’s cocreated and produced her own immensely popular Disney series Jessie, and currently stars on Netflix’s Insatiable. She knows her way around a TV set.

She also, thankfully, has a sense of direction, as we navigate ourselves to the right exit and arrive at our destination: Ferragamo’s New York Fashion Week dinner at Sant Ambroeus to celebrate the launch of #Gancini, the new monogram designed by women’s creative director Paul Andrew. Ryan, for her part, is decked out in the distinctive pattern, from her silk shirt to her very cute mini-bag, which we discover, after some maneuvering, does in fact fit her iPhone.

The actress has just landed in town from Los Angeles, and the event marks her first outing of the week; she attended a handful of shows last season, but, before that, her previous New York Fashion Week appearance came just a few months after Jessie ended its run in 2015. Ryan, like many young starlets before her, began to think about life after the Disney Channel. “My biggest fear is people being like, ‘We get it, you’re not a Disney kid anymore. Stop running around in booty shorts,’” she says. “That kind of public shaming on former kid stars...I was afraid of that being projected onto me. So as I grew and began to find myself, I just did so with discretion.”

Debby Ryan getting ready before attending the Salvatore Ferragamo dinner in New York City on Thursday, February 7, 2019. Photograph by Michael Beckert for W Magazine.

As happens to megafamous stars with more than 10 million followers, even leaving the house became a conscious decision. “You want to be able to go to the grocery store, you want to be able to bring your trash cans in, anything,” she says. “But you know, ‘Okay, I’m going to be stared at,’ and the narrative is not mine. If I’m tired and just flew to New York after shooting all night, and I’m not wearing makeup and people are used to seeing me with makeup, then it’s like ‘Debby’s looking rough and going through a tough time.’ Maybe Debby’s just not wearing an hour’s worth of makeup that’s been applied by an expert.”

To say the least, jumping into another TV series was the last thing on Ryan’s mind. Then came Insatiable. “I was very heavily urged to read the script,” she says. “Finally I was like, ‘Fine, if you want to hear another no, I’ll read it.’ I read it and was like, ‘Oh.’ It totally touched on this idea that I had had inside of me. I loved the duality of it, I loved that it was so broad and funny.”

In the show, Ryan plays Patty Bladell, a formerly overweight teen who, due to an accident, loses some weight and decides to seek revenge on those who have bullied her—a role that required Ryan to head back to high school once again. “For me to make the very intentional move to step back into being portrayed in high school, it had to introduce something that people had never seen from me,” she says. “With Jessie, she’s out of high school and would date seriously and was considering marriage. But you’ve never seen her make out with someone or wonder if she’s ready to sleep with someone.… People have never expected that from me, which is where I think a lot of the judgment on people who are on G-rated shows [comes from]; you’ve never imagined they would have a glass of wine at dinner or whatever. With [Insatiable], I did have a chance to reintroduce myself to people who thought that they knew me.”

The role certainly shows Ryan as you’ve never seen her before, with some truly wild plot lines. (“By episode three and four, you’re like, ‘This is kind of a weird show,’ but by the end you’re like, ‘Oh my God, this is bananas.") It was met with mixed reviews and was a bit polarizing on the Internet; then, in December 2018, it was revealed that it was Netflix’s ninth most binged original series of the year. “The thing that was validating was people being like, ‘I get it,’” she said. “If that was multiple millions of people internationally, or if that was 14 people, that’s cool.”

Debby Ryan getting ready before attending the Salvatore Ferragamo dinner in New York City on Thursday, February 7, 2019. Photograph by Michael Beckert for W Magazine.

Maridelis Morales

Ryan will head back to film season two at the end of the month, though, in true Netflix form, she has to keep mum on the plot. “I’ll say that we definitely step into a lot of the characters,” she offers. Before that, however, Ryan will wrap up a more under-the-radar project: a spot in Ryan Murphy’s Half Initiative Mentorship Program, which matches aspiring minority and female directors with current directors on various Murphy productions (Ryan is currently shadowing on Fox’s 911). “It’s really cool,” she said. “I haven’t even talked about it with my friends, because it is so special. [Directing] is so hard to break into because the thing they always say is, ‘We don’t want to take this chance on someone who has never had experience.... [This program] gives you unparalleled access and you ask the questions and learn the process, all the way from prep to post-production.”

This isn’t Ryan’s first foray into directing, however; she previously directed several episodes of Jessie, starting when she was just 19 years old. “Multiple directors were like, ‘Why aren’t you doing this?’” she said. “And I thought that they were just being like, ‘You’re bossy.’ But it turns out they were just also acknowledging that this is the marrying of my strengths and my weaknesses.”

But at the moment, Ryan is the one who needs direction—specifically on how to pose. Turns out, her Ferragamo sleeves are getting in the way of some very important jewelry—her brand-new engagement ring from longtime boyfriend (and now fiancé), 21 Pilots drummer Josh Dun. “He’s so good,” she said, showing off the indeed very good ring,. “I sent him a photo in, like, 2013 and he saved it. And on some phone call, I had mentioned my ring size, and he wrote it down. He’s...yeah.”

So yes, you can add wedding planning to Ryan’s already very busy schedule. “I’ve met with a few wedding planners,” she said. “It’s crazy. Anytime I’m doing an event [for work], the intimate parts of me are preserved. This is the most intimate. It feels actually weird, because Josh and I historically, when we’ve dated, there’s a lot of keeping it close to the chest…. But I think it will be a beautiful celebration.”