Sabrina Carpenter Says She Experienced Her 1st ‘Real Heartbreak’ 2 Years Ago

Sabrina Carpenter is opening up about going through her worst breakup in 2021 — right around the time she seemingly split from ex Joshua Bassett.

“I was heartbroken two years ago. I was in a really, really different mental place,” Carpenter, 24, told Zane Lowe during the Thursday, April 11, episode of Apple 1’s New Music Daily. “For me, that was truly my first heartbreak. And so I think when you’re going through something like that, you question everything about yourself and you take it really personal.”

The singer noted that after the split, her “instincts’ about herself and “ability to move throughout a room without questioning if people’s opinions are more important than you’re own” were called into question.

Carpenter added that her lyrics from her new song “Espresso” correlate with the type of thing she went through during her last breakup while also showcasing where she is at in her life currently.

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“That’s why even just ‘my give a f–ks are on vacation,’ it’s such a simple funny line, but so much of this song really kind of gets to a place where it really measures up with where I’m at right now, and you have to go through life to get there,” she shared, adding, “I think there’s a big difference between two years ago and now, but I’m just having fun now, which I think is the biggest difference.”

Rumors first began to swirl that she was dating Bassett, 23, in June 2020, when they were spotted in Los Angeles at a Black Lives Matter protest. At the time, the pair’s romance raised eyebrows because many fans were under the impression that the actor had been dating Olivia Rodrigo.

While Rodrigo, 21, and Carpenter never officially confirmed whether either of them had been seeing Bassett, both fueled the speculation in their music.

In January 2021, Rodrigo released her debut single, “Driver’s License," which referenced a “blonde” who was “so much older than me.”

That same month, Carpenter dropped “Skin,” where she sang the lyrics “Maybe we could’ve been friends / If I met you in another life.” At one point in the track, she seemingly referenced Rodrigo’s song title, with the lyric, “Don’t drive yourself insane.”

Carpenter went on to deny it was a diss track during a February 2021 appearance on The Late Late Show with James Corden.

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“People will make a narrative out of something always, you know?" she said at the time. "I think this was like a really interesting song for people to kind of misinterpret and make it into something that it wasn't really supposed to be in the first place."

Later that year, Carpenter’ put out her song “Skinny Dipping,” which was about trying to find closure after a breakup. Shortly after, she insinuated that she was single in a TikTok that featured audio saying, “I'm searching for love. I'm recently single … I think … and I'm looking for someone I can spend the rest of my life with."

Carpenter has since moved on with actor Barry Keoghan, who she has been linked to since December of 2023.