From Disney stars to short kings: A look inside Sabrina Carpenters’ dating history

Pocket-sized popstar Sabrina Carpenter is finally getting the success she deserves, as she takes the charts by storm with her new single Espresso. Along with this new-found fame, fans are curious as to who Sabrina Carpenter is dating, and you’d be surprised at the history of A-listers she’s been spotted with in the past.

She’s no stranger to internet controversy; she was in the middle of the Olivia Rodrigo/Joshua Bassett love triangle back in 2021, which put her under fire as a homewrecker. Since then, she has gracefully taken it in her stride and continued to make huge career moves, like opening for the Eras Tour in South America and Singapore this year. Here’s a deep dive of all her into the dating history of Sabrina Carpenter:

Bradley Steven Perry – 2014 to 2015

View this post on Instagram

A post shared by Bradley Steven Perry (@bradley_s_perry12)

Bradley and Sabrina are the only couple who publicly confirmed their relationship status on this list. Bradley was her fellow Disney star, who featured in Good Luck Charlie. It seems the pair dated from 2014 to 2015, when Sabrina was 15 and he was 16. She revealed in an interview at the time that he had asked her out in the cutest way, telling J-14: “[It was a] really unique way to ask someone out. [It was] like the pirate movies, like they do the little bottles and they put notes in them and send them across the ocean, like one of those, and [he] put a note inside. It was cute.”

Griffin Gluck – 2019

View this post on Instagram

A post shared by @griffingluck

Sabrina and Griffin Gluck met on the set of Tall Girl, a 2019 Netflix film in which they both starred in. Fans wondered if something was going on between the two, and in October, Sabrina publicly posted their relationship on her Instagram after a posting a photo of the pair wearing matching Halloween costumes. While it’s not a total hard-launch, they wore a couples costume recreating the full denim looks worn by then-public couple Britney Spears and Justin Timberlake in the early 2000s. Sounds pretty couple-y to me.

The two attended the premiere of Griffin’s movie, Big Time Adolescence, together in 2019, but were not seen together again after this. It seemed by the pandemic the pair had gone their separate ways.

Joshua Bassett – 2020 to 2021

The famous dramageddon love triangle that sent the internet into orbit back in 2021 was between Sabrina Carpenter, Joshua Bassett and Olivia Rodrigo. Sabrina and Joshua first sparked rumours of a potential romance in 2020 after being spotted together a handful of times – and the actress even appeared in Joshua’s Anyone Else music video.

They even wore matching Halloween costumes later in the year –  but neither Sabrina or Joshua ever confirmed their relationship and have only spoken positively of each other in interviews since. By 2021, Joshua was claiming he was single in an interview with GQ.

Fans everywhere theorised that Olivia’s song Drivers License was written about Joshua and Sabrina’s unconfirmed romance, but this was never discussed by any of the three stars. In fact, both Sabrina and Olivia have been significantly more successful in the music industry than Joshua, despite his release of various EPs throughout the controversy.

We’ll never get to the bottom of what truly happened, but Sabrina’s lead single from her 2022 album, Emails I can’t send, titled Because I liked a boy, finally revealed her side of the controversy, and the hate she received. Maybe it’s better that the internet stayed out of her relationship drama from now on.

Dylan O’Brien – 2022

Dating rumours sparked with Dylan O’Brien in September 2022 after DeuxMoi shared a photo of the two out together during NY Fashion Week. Fans also claimed they had seen the stars at a nearby bar together, but neither of the pair ever addressed these speculative romance rumours.

Shawn Mendes – 2023

View this post on Instagram

A post shared by Shawn Mendes (@shawnmendes)

Sabrina was caught spending time with Shawn Mendes on several occasions after celebrity gossip page DeuxMoi first reported that they had been seen out and about together in LA. After that, they were both seen at Miley Cyrus’ album release party for Endless Summer Vacation a few weeks later, where it was reported that they left the event with each other.

However, Shawn shut down all dating rumours between the pair, telling a Dutch news source that they should talk about his partnership with Tommy Hilfiger in their interview “probably more than Sabrina, but thank you.” Looks like whatever happened there blew over pretty quick.

Barry Keoghan – 2023 to present

An unlikely but adorable pairing, Sabrina Carpenter and actor Barry Keoghan seem to have been dating since 2023. The pair have found each other just as both of their careers skyrocketed, with Saltburn being crowned one of the biggest films of 2023. Fans are in awe of the couple, not only because they are both on the shorter side and would make perfect polly pockets, but because of Barry’s utter infatuation with her whenever they are together.

They tried to keep their relationship quiet at first, but now the pair have been openly debuted their romance, from the Oscars After Party to most recently the MET Gala. And of course, we can’t forget her iconic reference to his Saltburn role in her nonsense outro.

For all the latest music, film and entertainment news, memes and other fun stuff, like Pop Culture Shrine on Facebook.

Related stories recommended by this writer:

•This is how old all the Love Island 2024 cast members are, from youngest to oldest

• Memes, streams, popstar of dreams: How Sabrina Carpenter’s Espresso took over the world

•Sabrina Carpenter slammed for ‘copying’ artwork for new album cover Short n Sweet

Featured images via Instagram.