The queen of music just announced her engagement to NFL player Travis Kelce, her boyfriend since 2023. Those news made us look back at all the failed relationships our Taylor had to go through—and all the princes (and a few frogs) she had to kiss before finding the right one.
Besides her undeniable talent for writing beautiful, catchy songs, Taylor has also been in the spotlight for her romances. Over the years, she dated some of the most handsome men in Hollywood. Still, with none of them did she find true love—in fact, she went through several horror stories.
These Are All of Taylor Swift’s Ex-boyfriends
Here’s a look at Taylor Swift’s past relationships, from the early days of her career to the announcement of her engagement.
Joe Jonas
Without a doubt, Taylor’s relationship with Joe Jonas is one of the most remembered and criticized. Though they only dated for a few months in 2008, their breakup became iconic when Taylor revealed on The Ellen DeGeneres Show that Joe dumped her in a 27-second phone call.
Taylor Lautner
One of the fandom’s favorite exes. Taylor and Taylor (yes!) dated in 2009, when Lautner was at the peak of his career thanks to Twilight. A source revealed that there wasn’t much chemistry, so they broke up but remained friends. Years later, Lautner even appeared in Taylor’s music video for I Can See You alongside Joey King.
Lucas Till
After filming the You Belong With Me video together, there was a spark. However, after just one date they decided they were better off as friends. Funny enough, Lucas had confessed that Taylor was his teenage crush since he was 16.
Cory Monteith
Though never confirmed, multiple sources claimed that Taylor and Glee star Cory Monteith went on several dates between 2010 and 2011. Sadly, Cory passed away in 2013 from an overdose in a Vancouver hotel.
Jake Gyllenhaal
If you’re a Swiftie, you already know this tragic story. Jake and Taylor had a whirlwind romance that lasted only two months at the end of 2010. He reportedly dumped her right before New Year’s, leaving her devastated. In 2021, Taylor released the short film All Too Well (10-Minute Version), believed to be inspired by him, with Sadie Sink and Dylan O’Brien representing their age gap at the time (19 and 29).
John Mayer
Another highly controversial fling. In 2010, Taylor briefly dated John Mayer, and their 13-year age difference (she was 19, he was 32) sparked criticism. Taylor’s song Dear John is widely believed to be about him.
Conor Kennedy
In 2012, Taylor dated Conor Kennedy, grandson of Robert F. Kennedy. At the time, Taylor was 22 and Conor was 18. The two were spotted kissing in public and seemed inseparable, but the relationship only lasted three months. It’s rumored that her song Begin Again was inspired by him.
Eddie Redmayne
According to reports, Taylor and Eddie met during auditions for Les Misérables. They had a brief fling, but things ended—supposedly because Eddie didn’t want a long-distance relationship once Taylor didn’t land the role of Éponine.
Harry Styles
One for history books. In December 2012, Taylor and Harry Styles went public with their romance, sending the world into a frenzy. By early 2013, they broke up—but out of that heartbreak came Taylor’s iconic album 1989.
Matty Healy
In 2014, Taylor and The 1975 frontman Matty Healy started spending time together, even wearing shirts referencing each other at concerts (Taylor wore a 1975 shirt, Matty wore one with 1989). The romance fizzled quickly. Rumors resurfaced in 2023 about a possible rekindling, but it never happened—spoiler alert: Travis Kelce entered the picture.
Calvin Harris
Taylor’s relationship with the DJ was one of her longest, lasting from 2015 to 2016. The breakup wasn’t pretty, especially after disputes over credit for This Is What You Came For, which Taylor co-wrote.
Tom Hiddleston
One of the fandom’s favorites. Taylor and Tom started dating in 2016, and though they seemed head-over-heels—remember the “I ♥ TS” shirt?—the romance ended after just three months.
Joe Alwyn
Taylor’s longest relationship to date. She and actor Joe Alwyn started dating in 2016 and stayed together until 2023. Though Taylor wanted to settle down, reports suggested Joe struggled with her massive fame. Fans could only think: “That wasn’t it, Tay… that wasn’t it.”
Travis Kelce
Finally, the fairytale. Taylor and Travis met in 2023 after he attended an Eras Tour concert and joked about giving her a friendship bracelet with his number on it. Weeks later, they were spotted together, with Taylor cheering him on at games alongside his family. Now, nearly two years later, they’ve announced their engagement.
