Last summer Tucker Pillsbury, the 27-year-old singer-songwriter known as Role Model, was having what he describes as a quarter-life crisis. Originally from Portland, Maine, he was living in Los Angeles, attempting to write a follow-up to his debut album, Rx. He was the most homesick he’d ever been in his life, he tells me while tugging on a gold chain around his neck that reads “Mom.” Three and a half years into a very public relationship (and his first relationship ever)—one that was hard launched in GQ—with arguably the most influential woman on the internet, Emma Chamberlain, he found himself frequently visiting home, seeking some semblance of normalcy. “I was just instantly happier,” Pillsbury tells Vanity Fair. “Then I’d go back to LA and just sit there and go back to my sad little life…It’s just like, What am I doing with my life? Is me pursuing music and trying to reach whatever goal I have a good enough reason to be wasting my 20s in LA?”

Tucked into a corner of the Ludlow Hotel on the Lower East Side, in the middle of a heatwave, Pillsbury is wearing a white tank top, exposing an assortment of tattoos that say things like “may women rule the world,” and army green paint-splattered cargo pants. As he sips on a brightly colored spritz, he poses the questions that led him to his introspective sophomore album, Kansas Anymore, which is out Friday. “I seriously was considering, What am I doing in my life?” he says. “Very much having a crisis.” The album’s title is a nod to the film The Wizard of Oz. (“I’ve seen it once and I don’t even think I was fully conscious yet at that age, so the only thing I remember is the flying monkeys, and it scared the shit out of me,” he says.) Pillsbury was searching for a way home, a way back to himself.

It wasn’t that long ago that this was all a dream come true. In 2018, Pillsbury was studying film at Point Park University in Pittsburgh, experimenting with music equipment in his dorm room. His life changed when he caught the attention of the late rapper Mac Miller, who messaged him on Instagram and flew him out to LA, where Pillsbury later signed to Interscope Records.

As fate would have it, it was the same year Chamberlain moved to LA to pursue YouTube full time, having dropped out of high school. In 2020 the stars aligned, and in the way all great Gen Z love stories begin, Pillsbury slid into Chamberlain’s Instagram DMs after seeing her on TikTok to tell her that her ’fits were fire. Pillsbury’s first album, Rx, coincided with the singer falling in love for the first time, commemorating the honeymoon phase of their modern romance with starry-eyed, if not juvenile, songs like “Die for My Bitch” and “Masturbation Song.” He found himself completely consumed by the relationship. “You just sort of disappear off the face of the earth…and you make that person the center of your universe, which is romantic,” he says. “But it puts these blinders on you.”

Of course, when he was writing Kansas Anymore last year, he didn’t necessarily know it was going to be a breakup album, but by then Pillsbury was becoming increasingly disillusioned with LA and the industry at large. “I just wasn’t present [anymore],” he admits. Suddenly at a crossroads, he could feel his relationship slipping out from under him, but he kept writing. “We’re hanging on by threads / And I can’t hold it any harder on my end,” he confesses on “Oh, Gemini,” a song not-so-subtly named for Chamberlain’s astrological sign. When the couple officially called it quits, much of what he thought would be his sophomore album hit the cutting room floor, but not all of it. Over 13 tracks, Pillsbury longs for things to turn out differently but arrives at an understanding of why it had to end, exhibiting growth both personally and musically. The record is sonically softer and more mature for Pillsbury, inspired by the warm Americana sound that reminds him of home and built on his newfound guitar skills, which Chamberlain’s father taught him. From the brazen breakup anthem “Deeply Still in Love” to the earnest, somberly nostalgic “Frances” (which is Chamberlain’s middle name), the album chronicles the full spectrum of heartbreak.

With the record’s obvious nods to his famed ex, Pillsbury knows that the internet will try to extract intimate details about his relationship from his music, but he tries not to think about that. He’s ready to move on from his role as a famous person’s boyfriend, something he was once insecure about. “I will say this: Once we started putting out these singles, I fully started feeling like my own entity again, which is all I wanted,” he says. “That was the biggest weight off my shoulders.”

Beginning in September, Pillsbury will join forces with sad-girl-pop powerhouse Gracie Abrams, with the two going on tour and playing venues such as Radio City Music Hall. “I very much thought I was done opening for people for the rest of my life…but then this was just too perfect. I'm a massive fan of hers. I always have been,” says Pillsbury. “It’s one step closer to Miss [Taylor] Swift,” he adds jokingly, referring to Abrams’s stint as an opener for Swift’s Eras Tour. “I’m doing the tour so that I can get free tickets.”

In the past he’s expressed his disdain for artists pedaling their music on TikTok to please their labels. For this album cycle, though, he’s manufactured a digital evil twin on TikTok, Saint Laurent Cowboy, who does the posting for him. It’s a satirical account, but nonetheless it’s difficult to tell where the joke begins and ends. “I don’t know that man. I don’t support him. He’s trying to be me,” says Pillsbury, deadpan. “He’s pretending to be me, and I think it’s disgusting and I’ve tried to report it, but it won’t work. I just say, don’t follow him or engage with him.” All jokes aside, he says he will oblige and post what he needs to post on the eve of his album’s release before chucking his phone. But he quickly catches himself and backtracks. “I’ll be on my phone. Yeah, I’ll be on my phone,” he says, shaking his shaggy brown hair. “I’m very curious what people are going to think.”

But it’s not until now that he starts to consider what Chamberlain might think of the album, sinking into his seat as that reality sets in. “I don’t have an ounce of anger in me…. I think it shows in the album; it’s pretty much [me] just beating myself up,” he says, as evidenced by self-deprecating songs like “Scumbag.” “I don’t think it would be any news to her. I would never want to hurt someone’s feelings with my music. I don’t have that in my brain or heart.”

The album ends with a glimmer of hope for a pair of unlikely lovers on the song “Something, Somehow, Someday,” which calls to mind the Moldy Peaches indie-folk ballad “Anyone Else but You.” On it, Pillsbury sweetly sings, “But I believe they’re meant to be / Something, somehow, someday,” lingering on the possibility that their love story isn’t over quite yet. “It’s this open-ended hope to end everything off,” he says. “Leave the door open…almost leave it kind of unfinished. To me, that is the perfect ending. I wouldn’t have wanted to end on any other note.”

It’s mere hours before Kansas Anymore is officially out, and taking another sip of his drink, Pillsbury declares his quarter-life crisis a thing of the past, eager to remind people that these songs were written a year ago. “I genuinely am in such a better place in my life now. I have friends in LA for the first time,” he says, smiling. “I’m good now…. I’m more content in LA. I’m happy with the music I’ve made and where my career is at,” he adds slowly, pausing to convince himself of these things. “I feel like this is my happy ending—finally.”