Updated: November 12, 2025
Hey there, Swifties, Rodrigo fans, and everyone who’s been humming “Espresso” on repeat—Sabrina Carpenter is basically the queen of turning heartbreak into chart-toppers. At just 26, this blonde bombshell has gone from Disney darling to pop sensation, and her love life? It’s as juicy as her lyrics. If you’ve ever wondered about Sabrina Carpenter’s ex boyfriends, you’re in the right place. From teen crushes to steamy flings that inspired albums like Short n’ Sweet and her latest drop Man’s Best Friend, we’ve got the lowdown. Let’s spill the tea on her romantic rollercoaster, shall we?
Table of Contents
Early Disney Days: Puppy Love with Bradley Steven Perry
Remember when Disney Channel was the ultimate matchmaker? Sabrina’s first big romance kicked off back in 2014 with Bradley Steven Perry, the Good Luck Charlie heartthrob. These two were total high-school sweethearts—filming their shows side by side on the lot, sharing stolen glances between takes.
It all started with the cutest rom-com move ever: Bradley rolled up a note like a pirate’s message in a bottle and sent it her way. Sabrina spilled the deets in a 2014 J-14 chat, calling it “unique” and straight out of a movie. They dated for about a year, navigating that awkward teen phase with zero drama.
- How they met: On-set magic during Girl Meets World and Good Luck Charlie.
- Sweet moments: Matching Disney vibes and innocent dates—think arcade nights, not red carpets.
- The split: They fizzled out around 2015, but no bad blood. Bradley even shouted her out on his podcast The Sit and Chat in 2024, saying, “My first girlfriend’s doing way better than anyone else in the world.”
These days, Bradley’s with Natasha Bure, but that first love clearly shaped Sabrina’s playful songwriting roots.
On-Set Sparks: Griffin Gluck and the Tall Girl Connection
Fast-forward to 2019, and Sabrina found her next leading man on the Netflix set of Tall Girl. Enter Griffin Gluck, the charming actor from Locke & Key and 13 Reasons Why. Their chemistry was off the charts—fans shipped them harder than the plot twist.
Sabrina hard-launched the romance with an Instagram post of them in matching Stranger Things Halloween costumes. Adorable, right? They kept things low-key, bonding over late-night script reads and coffee runs.
- Duration: Roughly a year, wrapping up quietly by 2020.
- Fun fact: They reunited for Tall Girl 2 in 2022—awkward? Nah, pros handling it like champs.
- Post-breakup vibe: Griffin’s thriving in indie films, and Sabrina’s channeled that cozy energy into tracks like “Because I Liked a Boy.”
It was a sweet, supportive chapter that proved Sabrina’s got a knack for co-star crushes.
The Love Triangle That Broke the Internet: Joshua Bassett Drama
Oh boy, 2020-2021? Peak pop culture chaos. Sabrina got tangled in the ultimate love triangle with Joshua Bassett—fresh off his split from Olivia Rodrigo. Spotted at a Black Lives Matter protest together, the vibes were electric. But then Olivia dropped “drivers license,” that gut-wrenching ballad about her ex moving on with a “blonde girl.” Oof.
Sabrina clapped back with “Skin,” shading the shade, while Joshua responded with “Crisis.” It was messy, viral, and honestly, the drama we didn’t know we needed.
- Timeline: Summer 2020 to early 2021—short but explosive.
- Impact: Inspired Olivia’s Sour, Sabrina’s Emails I Can’t Send, and endless TikTok theories.
- Today: All’s forgiven! A 2025 Grammys fan vid showed Sabrina and Olivia hugging it out—no beef, just boss babes.
This saga turned Sabrina into a lyrical warrior, proving she thrives on turning pain into power.
High-Profile Flings: Shawn Mendes, Dylan O’Brien, and Barry Keoghan
Sabrina’s recent roster reads like a Hollywood script. In 2021, Deuxmoi tipped off a steamy makeout with Maze Runner star Dylan O’Brien in NYC—quick, fiery, and over before it hit headlines.
Then, 2023 brought Shawn Mendes. Spotted on a flirty dinner date and leaving Miley Cyrus’s party hand-in-hand, fans went wild. But it was brief; Shawn rekindled with Camila Cabello, leaving Sabrina to vent in Short n’ Sweet‘s “Taste”—a petty (and petty brilliant) warning to his rebound.
Enter Barry Keoghan, the Saltburn bad boy. They met at Paris Fashion Week in September 2023, went Insta-official with friendship bracelets at her shows, and he starred as her jailbird BF in the “Please Please Please” video. It was hot, public, and over by December 2024—sources say careers clashed, but Barry hyped her 2025 Grammy noms till the end.
- Dylan: One-night spark, pure Hollywood heat.
- Shawn: Low-key dates, high-stakes heartbreak—fueled “Taste” and “Go Go Juice” name-drops.
- Barry: Year-long whirlwind; ended amicably, with Sabrina focusing on self-growth.
As of now, she’s single and slaying—her latest album Man’s Best Friend (dropped September 2025) slyly nods to these exes in “Go Go Juice.”
Conclusion: Sabrina’s Heartbreak Hits Keep on Giving
Whew, what a ride! Sabrina Carpenter’s ex boyfriends—from Bradley’s bottle-note charm to Barry’s red-carpet romance—have all added flavor to her fearless artistry. She’s proof that love doesn’t have to last to inspire magic; it just needs to spark those killer lyrics. Whether it’s shading an ex or owning the single life, Sabrina’s unapologetic glow-up is everything. Who’s next on her playlist? Only time (and maybe a new album) will tell. What’s your fave Sabrina heartbreak anthem? Drop it in the comments—let’s chat!