Role Model gets candid about crisis moments after Dakota Johnson breakup

Role Model is opening up about some of the most uncertain moments of his personal and professional life as he reflects on the difficult period that inspired his latest album.

The singer, whose real name is Tucker Pillsbury, recently discussed the emotional journey behind Chuck Timely & The Hourglass. The album was shaped during a roughly two-year period when Pillsbury was single and struggling to understand where his life was heading. (Rolling Stone Australia⁠)

Speaking about that period, Pillsbury said he often felt lost and experienced repeated moments of questioning where he belonged. While friends around him were getting married, falling in love and moving into new stages of their lives, he felt as though he was standing still.

The emotional uncertainty became an important part of the album. Pillsbury explained that he was writing about his feelings in real time, including what he described as quarter-life and identity-crisis moments. He also admitted that he did not know whether he should immediately enter another relationship or take time to focus on himself. (Rolling Stone Australia⁠)

The experience was complicated by his unusual lifestyle. While many of his friends had traditional jobs and predictable weekends, Pillsbury’s career kept him on the road and surrounded by work. Despite his professional success, he said that his career reaching a new level while making the album could feel overwhelming.

That emotional period eventually became the foundation for Chuck Timely & The Hourglass, turning uncertainty and loneliness into music.

Pillsbury’s romantic life has also attracted significant attention. He was linked to actress Dakota Johnson, but reports confirmed in August 2026 that the pair had ended their relationship after less than a year together. Their split came shortly after Pillsbury had publicly discussed their relationship and revealed that Johnson contributed a spoken-word cameo to his album on the track “Love I You.” (E! Online⁠)

Despite the recent breakup headlines, the emotions behind the album largely predate his relationship with Johnson. The two-year period that inspired much of the record followed his 2023 split from Emma Chamberlain and became a period of deep personal reflection. (Rolling Stone Australia⁠)

Now, Pillsbury appears to be embracing those difficult experiences rather than hiding them. His latest project transforms feelings of being stuck, lonely and uncertain into something creative and deeply personal.

For Role Model, the album is more than another collection of songs. It represents a period when he was trying to figure out who he was, where he was going and what he truly wanted from life.