Sabrina Carpenter’s Dating History: A Timeline of the Espresso Singer’s Relationships

Sabrina Carpenter is having a moment right now, from the release of her new studio album Short n’ Sweet, releasing the song of summer Espresso to performing as a support act for Taylor Swift’st Eras tour, she has done it all. To add to it all, her other song Please Please Please has also been making the headlines. Reason? The music video features Carpenter’s current beau Barry Keoghan.

 

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It has been evident for quite some time that the two have been dating, what with Keoghan frequently getting spotted wearing friendship bracelets with Sabrina’s name and attending all of her concerts.

Though there has been some scepticism surrounding the Saltburn actor’s fatherhood and the whereabouts of his child from an earlier relationship, the ‘Nonsense’ singer seems unfazed by these concerns.

While she seems smitten by Keoghan right now, this isn’t Carpenter’s first rodeo. She has experienced innocent Disney romances, relationships that have inspired songs and albums, and an alleged love triangle with Joshua Bassett and Olivia Rodrigo. 

With Carpenter’s popularity at an all-time high, it is worth delving into her romantic past.

But before we deconstruct Sabrina Carpenter’s dating history, let’s take a look at the timeline of her rumoured romances.

• Bradley Steven Perry: 2014 – 2015
• Griffin Gluck: 2019
• Joshua Bassett: 2020 – 2021
• Dylan O’Brien: 2022
• Shawn Mendes: 2023
• Barry Keoghan: 2023 – present

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Breaking down the list of Sabrina Carpenter’s alleged ex-boyfriends 

From her rumoured flings with Shawn Mendes and Dylan O’Brien to her Please Please Please romance with Irish actor Barry Keoghan, here’s deep diving into Sabrina Carpenter’s dating History. 

Bradley Steven Perry (2014-2015)

Occupation: Actor
How did they meet: On the set of a Disney show

The first name in Sabrina Carpenter’s dating History is of her fellow Disney alum Bradley Steven Perry. The two dated back in 2014 for over a year when Sabrina was just 15 years old and Bradley was 16. Though they both were working for Disney at the time, they weren’t on the same show – Perry was in Mighty Med while Carpenter was acting in Girl Meets World.

In a conversation with J-14, the songstress revealed that Perry had asked her out in the sweetest way possible: “[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)

Occupation: Actor
How did they meet: On the set of Tall Girl 

Sabrina and Griffin Gluck crossed paths for the first time while working on the 2019 Netflix movie Tall Girl. Fans had a feeling that there was something brewing between them, and in October, Carpenter subtly revealed their alleged relationship on Instagram by sharing a picture of them dressed in matching Halloween costumes. The two had replicated the iconic full denim outfits worn by Britney Spears and Justin Timberlake in the 2000s. 

Later in 2019, the duo attended the premiere of Big Time Adolescence, a movie in which Griffin starred alongside Pete Davidson. However, when the global pandemic hit in 2020, it appeared that the two artists had gone their separate ways.

Joshua Bassett (2020 – 2021)

Occupation: Actor and singer
How did they meet: Not known  

Next up in Sabrina Carpenter’s dating History, we are breaking down one of pop culture’s most famous – or infamous – love triangles.

American actor and singer Joshua Bassett was allegedly at the centre of a highly publicised love triangle involving Sabrina Carpenter and fellow singer Olivia Rodrigo in 2020 and 2021.

There was speculation among fans that Rodrigo’s popular song Drivers License was inspired by the rumoured affair between Joshua and Sabrina, although this was never officially confirmed.

For context, dating rumours between Carpenter and Bassett began circulating in 2020 after they were spotted together on multiple occasions, with the Espresso singer even making an appearance in Joshua’s music video for ‘Anyone Else’. The two even wore matching Halloween costumes later that year, but neither of them ever confirmed their relationship. In interviews, they have only spoken positively about each other.

Later in 2021, Joshua stated in an interview with GQ that he was single.

Dylan O’Brien (2022)

Occupation: Actor
How did they meet: At fashion week  

In 2022, Sabrina found herself in another alleged romance, this time with The Maze Runner actor Dylan O’Brien. Dating rumours first sparked in September 2022 after celeb gossip page DeuxMoi shared a photo of the stars hanging out during New York Fashion Week.

Fans also claimed they had been seen at a nearby bar together, but neither ever confirmed the rumours of their romance. In any case, whatever it was that the two shared eventually fizzled out and the two went their separate ways. 

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Shawn Mendes (2023)

Occupation: Singer
How did they meet: Allegedly on a date  

Following a few dates with Dylan O’Brien, Sabrina found herself in a romantic entanglement with none other than Shawn Mendes. The two were spotted hanging out a few times after DeuxMoi first reported that they had been out together in Los Angeles sometime in February 2023.

Later, they were both spotted at Miley Cyrus’ launch party for Endless Summer Vacation, where they reportedly left the party together. However, Shawn shut down any dating speculation by telling RTL Boulevard that they should instead talk about his partnership with Tommy Hilfiger in their chat. He said, “We are not dating but I think we should talk about Tommy Hilfiger probably more than Sabrina. Thank you.”

Barry Keoghan (2023 – present)

Occupation: Actor
How did they meet: Not known  

The last name (and most current) name in Sabrina Carpenter’s dating history is Saltburn hottie Barry Keoghan. Carpenter has been dating the Irishman since the end of 2023 and he’s pretty much become a Sab groupie. The two made their relationship official with the songstress’ music video for Please Please Please, which featured Keoghan. 

Fans seem obsessed with the couple, not only because they’re both doll-sized, but also because of the puppy dog expressions Keoghan seems to wear whenever he’s in the presence of his lady love. It’s enough to make fans believe that he’s certainly obsessed with her.

The new Hollywood sweethearts have been openly adoring one another by making many red-carPet appearances together, from the Oscars after parties to the 2024 MET gala.

(Header and feature image courtesy: Instagram/Sabrina Carpenter/Barry Keoghan/Shawn Mendes)

This story first appeared on Augustman Malaysia.

Frequently Asked Questions (FAQs)

– Who is Sabrina Carpenter dating currently?
Sabrina Carpenter is currently dating actor Barry Keoghan. 

– How long did Sabrina Carpenter and Shawn Mendes date?
Sabrina and Shawn Mendes were rumoured to be dating in February 2023. They were spotted hanging out at Miley Cyrus’ launch party for ‘Endless Summer Vacation’, though neither ever confirmed the nature of their relationship.