Okay, so Taylor Swift is officially engaged to Travis Kelce (yes, football’s golden boy put a ring on it!), but let’s not forget the iconic roster of famous exes who inspired some of the greatest breakup anthems of our generation. Taylor’s dating history is practically a playlist, and every ex left behind a lyric or two. Let’s sip some tea, shall we?
Joe Jonas (2008)
Ah, the one that started it all. Baby Taylor and Joe Jonas had a whirlwind teen romance… until Joe broke up with her over a 27-second phone call (yes, really). Out of the ashes came classics like Forever & Always and Mr. Perfectly Fine. We stan a queen who turns heartbreak into bops.
Lucas Till (2009)
You probably remember him as the cute boy from the You Belong With Me video. They dated super briefly, and honestly, it was so low-drama that even Swifties sometimes forget it happened. A rare peaceful chapter.
Taylor Lautner (2009)
The “Taylor Squared” era! They met on the set of Valentine’s Day and were adorable together. But when it fizzled, Taylor (Swift) surprised everyone by writing Back to December, a rare apology song basically saying, “Yeah, I messed this one up.”
John Mayer (2009–2010)
Oof. This one gets messy. John was older, Taylor was young, and when it ended, she did what she does best: wrote Dear John, one of the most gut-punching breakup tracks in her catalog. He was not amused.
Jake Gyllenhaal (2010)
Cue All Too Well (10 Minute Version) — arguably Taylor’s magnum opus of heartbreak. Their short but intense relationship turned into a whole cultural moment, complete with that infamous scarf and lyrics that still haunt Jake to this day.
Conor Kennedy (2012)
For one summer, Taylor was basically an honorary Kennedy. She even bought a house near his family’s compound in Hyannis Port (casual). Their romance was short-lived, but the vibe was very “young love in a Nicholas Sparks novel.”
Harry Styles (2012–2013)
Ah, “Haylor.” The paparazzi photos! The Central Park stroll! The matching necklaces! Their relationship may have been brief, but it gave us Style, Out of the Woods, and the chaotic energy of I Knew You Were Trouble. Iconic.
Calvin Harris (2015–2016)
This was one of her longer, more “normal” relationships — until it wasn’t. They looked super cute on Insta, but things ended badly, and let’s just say This Is What You Came For drama got messy fast.
Tom Hiddleston (2016)
Remember the “I ♥ T.S.” tank top? Yep, that was Tom. Their summer romance was hot, fast, and extremely public. Some thought it was a PR stunt, but Tom later insisted it was real. Taylor allegedly turned it into Getaway Car.
Joe Alwyn (2016–2023)
This was the long-term era. Taylor and Joe kept things super private for years, with fans convinced they’d secretly gotten married at some point. He inspired some of her most romantic work (Lover, anyone?). But after six years, it ended quietly — for Swift standards, anyway.
Matty Healy (on-and-off, most recently in 2023)
Taylor and The 1975 frontman had some sparks back in 2014 and briefly reconnected in 2023 after her split from Joe Alwyn. Let’s just say it was… chaotic. Fans were divided, but it didn’t last long.
And now… Travis Kelce (2023–Present)
The fairytale twist! America’s sweetheart meets America’s football star, and now they’re engaged. Who would’ve thought a friendship bracelet at a Chiefs game would lead to this?
Which Ex Inspired the Best Songs?
- All Too Well (10 Minute Version) — Jake Gyllenhaal
- Back to December — Taylor Lautner
- Dear John — John Mayer
- Style + Out of the Woods — Harry Styles
- Forever & Always + Mr. Perfectly Fine — Joe Jonas
- Lover — Joe Alwyn
Taylor’s love life has basically doubled as a musical diary for over a decade — and honestly, we’re not mad about it. Every ex gave us an era, every heartbreak gave us a hit, and now with Travis Kelce, we might just be entering her happily ever after era.