How Well Do You Know Taylor Swift's Boyfriends?

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No one writes a love song like Taylor Swift — and she’s had plenty of causes for both joy and heartbreak over the years. From the 10-minute-long extended version of "All Too Well," which is rumored to be inspired by Tay's 2010 breakup with actor Jake Gyllenhaal, to singing about falling in love on "Lavender Haze," the Grammy award-winner uses her music to give her fans insight into her personal life and the men she's loved and lost. Even if she is never ever ever getting back together with any of them, it’s still fun to remember the inspo behind some of her hits. Look back on the full timeline of Taylor Swift’s boyfriends and test your knowledge of the relationships below.

Joe Alwyn (May 2017 - 2023)

celebrity sightings in new york city october 6, 2019
Robert Kamau - Getty Images

After six years, Taylor officially called it quits with her British beau, Joe Alwyn. While the duo kept the deets of their ship under wraps in the public eye, Tay spilled the tea on songs written about Joe with Joe under the alias William Bowery on her Folklore, Evermore, and Midnights albums.

Tom Hiddleston (June 2016-September 2016)

taylor swift boyfriends
Newspix - Getty Images

OK, we’ll admit that we never would have seen this one coming — and it all started with a dance-off at the Met Gala??? Taylor and Tom were photographed kissing on a Rhode Island beach a few days after her breakup with Calvin Harris. Tom also gets a jab during the "Look What You Made Me Do” video,” which features a squad of male dancers wearing "I <3 TS" shirts. Just like the one that the internet trolled Tom for wearing during their Fourth of July weekend.

Calvin Harris (February 2015-June 2016)

One of Taylor’s more lengthy romances, the couple met through mutual friend Ellie Goulding in February 2015 and celebrated their anniversary one year later with a homemade cake.

So sweet! Then, things went sour. Taylor writes about needing a reason to leave a relationship in “Getaway Car,” and she made that escape by breaking things off with Calvin and sliding into a relationship with Tom Hiddleston. Calvin FREAKED out on Twitter, and Taylor referenced the bad blood in the video for "Look What You Made Me Do.” Zombie Taylor crawls out of her grave by a tombstone reading "Nils Sjoberg," AKA the pseudonym she used as her writing credit on Harris and Rihanna's hit track, "This is What You Came For.”

Harry Styles (December 2012-January 2013)

taylor swift boyfriends
David Krieger/Bauer-Griffin - Getty Images

The two pop power stars (#HAYLOR) joined forces for a relationship after a rumored fling the April before. Taylor reportedly wrote “I Knew You Were Trouble” about Styles and announced their breakup by tweeting a lyric from the song. She referenced the relationship again two years later in “Out of The Woods.”

Conor Kennedy (July 2012-October 2012)

Taylor dated the grandson of JFK, and pair were photographed kissing and canoodling all over Massachusetts. They ultimately broke up over distance issues, but Conor gets a favorable call-out as the boy who thinks T-Swift is funny in “Begin Again.”

Jake Gyllenhaal (October 2010 - January 2011)

Jake is rumored to be the cause of much of the anger behind the “Red” album, including the song, “The Last Time,” which Taylor said is about dating an unreliable guy who keeps coming back. So, you can guess what other tune is also about him...

Cory Monteith (April 2010 - May 2010)

Never officially confirmed, Taylor and late "Glee" star Cory Monteith were often see cozying up to one another. “Mine” from “Speak Now” is also rumored to be about Cory, a boy who Taylor “just barely knew put his arm around me by the water, and I saw the entire relationship flash before my eyes."

John Mayer (December 2009 - February 2010)

taylor swift boyfriends
Kevin Mazur - Getty Images

Taylor, who is 11 years younger than John, was 19 at the time of the relationship. The age difference proved to be a point of pain, as she sings in her “Dear John” hit, "Don't you think I was too young to be messed with? The girl in the dress cried the whole way home. I should've known."

Lucas Till (March 2009 - April 2009)

Lucas was the object of Taylor’s affection in the “You Belong With Me” video, but the short length of their relationship says otherwise. It sounds like a chill breakup though. “I really just liked her as a friend. That’s the only reason that didn't work out,” Lucas said.

Taylor Lautner (August 2009 - December 2009)

The two Taylors met on the lovey-dovey set of “Valentine’s Day” and brought their rom-com romance into reality for three short months. The relationship might have ended with the rough night described on “Back To December,” as boy Taylor sure fits the “tan skin” and “sweet smile” description.

Joe Jonas (July 2008 - October 2008)

taylor swift boyfriends
Jeff Kravitz - Getty Images

Joe Jonas will forever be remembered as the ex that broke up with Taylor during a 27-SECOND PHONE CALL. Honestly, so messed up. The breakup in 2008 led Taylor to write "Last Kiss" and "Forever and Always,” as well as the more positive “Holy Ground” after the pain numbed a bit.


1. The Caribbean — SO steamy!; 2. Hiddleswift; 3. "Ole"; 4. They had a HUGE fight.; 5. A house near his home in Cape Cod.; 6. BY SKIPPING HER PARTY LIKE A TOTAL JERK!!!; 7. Ellen; 8. Tweeted, deleted, and then re-posted bitter things about her birthday.; 9. Taylor Swift; 10. That "Back To December" was about him.; 11. True

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