In the world of pop stars, Sabrina Carpenter's dating history stands out with its unique twists and turns. From her early days with fellow Disney kids to more recent romances, Carpenter's love life has been a topic of much interest. Let's take a closer look at the details of her dating history.

Unraveling Sabrina Carpenter's Dating Tale

Bradley Steven Perry

Sabrina Carpenter's first public romance was with Bradley Steven Perry. In 2014, they began dating and remained together for a year. Little is known about their relationship, except for the unique way Perry asked Carpenter to be his girlfriend. It was like a scene from a pirate movie, with notes in bottles sent across the ocean. This cute gesture showed the early spark between them. Just a few months later, Perry was by Carpenter's side at her Alice in Wonderland-themed 16th birthday party in Los Angeles. This event solidified their connection during that time. During a January 2024 episode of Perry's podcast, he mentioned an ex-girlfriend who "does a little bit of singing," and many listeners believed he was referring to Carpenter. His words showed that even after their breakup, she still held a special place in his heart. Perry is now dating Candace Cameron Bure's daughter, Natasha Bure.

Griffin Gluck

Carpenter and Griffin Gluck seemed to meet on the set of Netflix's 2019 comedy film Tall Girl. They were later photographed at a Los Angeles premiere party for Gluck's Netflix series Locke & Key in February 2020. A month later, Carpenter supported Gluck at the premiere of his film Big Time Adolescence. It's unclear when they ultimately split, but they reunited for Tall Girl 2 in 2022. This shows the complex nature of their relationship and how it continued to have moments even after some time apart.

Joshua Bassett

Carpenter and Joshua Bassett first sparked romance rumors when they were spotted at a Black Lives Matter protest in L.A. in June 2020. Before dating Carpenter, Bassett was in a relationship with singer Olivia Rodrigo. The trio made headlines for several months after Rodrigo released her song "Driver's License" in January 2021. The track was about an ex moving on and included a reference to a "blonde girl," which was believed to be a subtle nod to Carpenter. Later that same month, Carpenter seemingly responded with the song "Skin" and Bassett voiced his support. In a since-deleted Instagram post, she shared her thoughts on the work, stating that some lines addressed a specific situation while others related to other experiences. Amid all the drama, their duet titled "We Both Know" was scrapped after initially delaying the release. Bassett later told GQ in June 2021 that he refused "to feed into any of the bull—-" and identified as a member of the LGBTQ+ community. Later that December, he revealed that he was single and said, "I'm good on my own. I don't need somebody else."

Shawn Mendes

Romance rumors about Carpenter and Shawn Mendes began to swirl in February 2023 after they were seen out and about in L.A. together. The following month, E! News reported that they were spotted leaving Miley Cyrus' album release party in the same car. Shortly after, Mendes told the Dutch television show RTL Boulevard that he and Carpenter were "not dating." However, fans were convinced that several songs on Carpenter's album Short n' Sweet are about the "Treat You Better" singer being hung up on his ex-girlfriend Camila Cabello. This shows the impact of their rumored relationship on both their careers and the public's perception.

David Dobrik

In August 2023, Page Six reported that Carpenter and YouTuber David Dobrik partied together after her set at Lollapalooza in Chicago. The "Bed Chem" singer seemingly shut down the dating rumors when she posted photos from the festival on Instagram and wrote, "sry i don't date lollapaloozas." This shows her attempt to clarify the situation and move on from the rumors.

Barry Keoghan

Carpenter and Barry Keoghan first sparked dating rumors in December 2023 when they were spotted having dinner together in L.A. The couple eventually confirmed their romance in February 2024 and made their red carpet debut at the Vanity Fair Oscars afterparty the following month. Shortly after, they attended the Met Gala in May, and the actor starred in the singer's "Please Please Please" music video. Not long after, breakup rumors surfaced, and a source exclusively told PEOPLE that their relationship was "on and off" by the end of the summer. In November 2024, Keoghan appeared on The Louis Theroux Podcast and called himself "incredibly blessed" to have Carpenter in his life. A month later, an insider told PEOPLE that the pair had "decided to take a break." This shows the ups and downs of their relationship and how it played out in the public eye.