When did Role Model and Emma Chamberlain date? All about singer’s personal life amid SNL debut

As Life & Style revealed, Role Model is believed to be single after ending his relationship with model and internet personality Emma Chamberlain in October 2023. Their three-and-a-half-year romance had drawn public attention, and later found its way into the heart of his record Kansas Anymore. Looking back, the singer told Nylon,

“I have no regrets, and it’s a beautiful time in my life that I’m proud of. I honestly never thought I would be in a relationship for three and a half years, and the fact that I was and that it was beautiful pretty much the entire time — I’m just very thankful. At the end of the day, I think the best thing I took away from it is knowing that I can do that and knowing that I can do that again at some point when I want to or when I’m ready.”

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Then came his much-talked-about Saturday Night Live appearance. People reported that on October 11, during the show’s second episode of season 51 hosted by Amy Poehler, Role Model performed his viral single “Sally, When the Wine Runs Out.” At one point, he called out, “Where’s my Sally tonight?” only for Charli Xcx to stride onto the set moments later. Wearing a black skirt, dark shades, and a “Max’s Kansas City” shirt, she instantly sent the studio crowd into cheers.

The outlet added that the look might have carried a hidden message. Role Model had sported the same shirt in SNL’s promotional clips. The nod fit neatly with his July 2024 album Kansas Anymore and New York’s connection to the legendary Max’s Kansas City nightclub. Charli’s cameo continued his recent trend of inviting surprise “Sally” guests to join the stage.

Emma Chamberlain and Role Model’s viral relationship and the album it inspired:

Distractify once noted how Role Model and Emma Chamberlain’s romance became a viral sensation, thanks to their overlapping YouTube fame. Emma had first turned to creating content after feeling disconnected from traditional schooling, ultimately transforming her curiosity into a multimillion-view career. Around the same time, Role Model transitioned from relative obscurity to a music career, an opportunity that came after Mac Miller encouraged him to step into the industry. His quick rise mirrored the pace of their much-discussed relationship.

In a conversation with Vanity Fair, the musician revealed that their breakup had directly influenced the creation of Kansas Anymore.

“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, 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,” he explained.

Reflecting on his outlook after the breakup, he added,

“I genuinely am in such a better place in my life now. I have friends in LA for the first time. 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.”

The making of Role Model: Tucker Pillsbury’s unlikely path to music

During an appearance on Today on August 29, Tucker Pillsbury, better known by his stage name Role Model, was asked by Craig Melvin how the moniker came about.

"That's a good question, you know what, I thought it was funny at the time that I chose it, and you don't think ahead that if it works out, you're stuck with that for life. So here we are on live TV as Role Model, " explained Tucker Pillsbury.

Despite the self-deprecating humor, he had grown comfortable with both names. To fans, he was either Role Model or simply Tucker, a balance he seemed to enjoy. According to NBC, Pillsbury was born in Maine on May 15, 1997, and released his first EP, Arizona in the Summer, when he was 20. Yet, music hadn’t always been his plan.

Life & Style reported that Tucker Pillsbury originally pursued film studies at Point Park University in Pittsburgh after high school. Two wrist injuries, one from skiing at Sugarloaf Mountain and another from skateboarding, kept Tucker Pillsbury confined to his dorm. There, surrounded by borrowed instruments and recording gear, he began experimenting with Logic Pro and making rap mixtapes. As Tucker Pillsbury's academic performance declined, he decided to leave college and focus on music entirely.

According to The Hollywood Reporter, on May 19, 2025, it was confirmed that Mark Ruffalo and Tucker Pillsbury (Role Model) would star alongside Natalie Portman in Good Sex, a romantic comedy directed by Lena Dunham for Netflix. The project marks Pillsbury’s first on-screen role, officially introducing the musician to the world of acting. What started as a passion project has become a full-blown creative odyssey, and for Role Model, the next act is only just beginning.

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