When it comes to songs about heartbreak, Taylor Swift is without peers. Listeners of “I Knew You Were Trouble” spend much time figuring out which of the singer’s exes inspired a particular song.
The re-recording and re-release of her earlier albums like “Fearless” and “Red” have brought back the topic of her ex-boyfriends. Check out Taylor Swift’s ex-boyfriends.
Joe Jonas
Taylor and Nick Jonas dated briefly in 2008, but their 25-second phone call breakup was the impetus for her second album, “Fearless.”
Famous DNCE songs, including “Forever & Always,” “Last K!ss,” “Better Than Revenge,” and “Mr. Fine,” was written with him in mind. The album ultimately earned her first Grammy Award.
When Swift hosted the inaugural episode of “Saturday Night Live” in 2009, she opened with a performance:
“You might think I’d bring up Joe, that guy who broke up with me on the phone. But I’m not going to mention him in my monologue. Hey, Joe! I’m doing really well and I’m hosting ‘SNL’ but I’m not going to write about that in my monologue”.
Lucas Till
After meeting on the set of “Hannah Montana: The Movie,” in which Swift had a cameo appearance, the two went on to co-star in Swift’s music video for “You Belong With Me” in 2009. The pair broke off their engagement a few months later after deciding they were better off being friends.
Taylor Lautner
The two actors, collectively known as “Taylor Squared,” met on the set of “Valentine’s Day,” in which they portrayed high school sweethearts. The couple reportedly broke up because Lautner had more feelings for Swift than she had for him. Swift reportedly wrote “Back to December” to apologize to the “Twilight” actress for their relationship.
Cory Monteith
Swift and the late “Glee” star dated for just a short time, but she took the time to write him a beautiful song expressing her emotions. The song “Mine” is about a kind guy she hardly knows named Monteith.
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John Mayer
Working together on “Half of My Heart” led to a short-lived rom@nce between the two. Swift, at age 20, released a song called “Dear John,” which she ripped against the “Gravity” singer.
To paraphrase Swift’s lyrics: “Dear John, I see it all now, it was terrible / don’t you think 19 is too young to be played by your dark, twisted games.” As a songwriter, Mayer said, “I will say that I think it’s sort of cheap songwriting.”
Jake Gyllenhaal
Swift had much to say about the actor on her newly-released album “Red,” which has an acidic 10-minute version of “All Too Well,” a song about the couple’s divorce, even though they dated for just three months in 2010.
The songs “We Are Never Getting Back Together,” “State of Grace,” and “The Moment I Knew” are said to have been inspired by him. She was taken aback when Gyllenhaal broke up with Swift by text message. He gave the cause of their age gap.
Conor Kennedy
In 2012, Swift dated Conor Kennedy, Robert F. Kennedy’s grandson. The strange combination of Kennedy (age 18) and Swift (age 22) did raise some eyebrows.
Swift’s love for the Kennedy family before her relationship with Conor. She wrote the song “Starlight” on Bobby and Ethel Kennedy’s rom@nce.
Harry Styles
In December 2015, the “Haylor” pair was seen on their first public outing, a walk around Central Park. The young couple’s three-month courtship was the talk of the “Swifties” and “Directioners” of the time, but it ultimately ended in heartbreak.
At the Grammys that same year, Taylor performed “We Are Never Getting Back Again” with an apparent barb at Styles, who was in attendance.
Calvin Harris
The Scottish DJ and the Singer sparked dating rumors when they were seen at Whole Foods in March 2015 wearing identical outfits. They went public with their relationship in May by attending the Billboard Music Awards as a couple and showing some PDA in front of the cameras.
After more than a year together, Harris terminated the relationship in March 2016 in what her close pals call a “brutal” breakup.
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Tom Hiddleston
At the 2016 Met Gala, Tom Hiddleston and Taylor Swift shared a dance floor. They were together for a month when images of them k!ssing on a Rhode Island beach surfaced, proving it. Swift was as surprised as everyone else by the “Hiddleswift” union.
She reportedly wrote “Getaway Vehicle” to express her sorrow at moving on so quickly following her split with Harris. Nonetheless, the couple broke up not long after that.
Joe Alwyn
Swift was in her most committed and discreet relationship in 2016. After meeting actor Joe Alwyn at the 2016 Met Gala, she started dating him, albeit the public didn’t find out about it until the following year. The forthcoming documentary “Miss Americana” will include her saying:
“I was falling in love with someone who had a very normal, balanced existence. We both agreed that we wanted our relationship to be private. I felt good. Yet I wasn’t happy in the ways I’d been taught to be happy. It was joy without interference from anyone else. We were just pleased”.
The pair split up in April 2023 after being together for almost six years.
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