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Taylor Swift is well-known for her storytelling about the ups and downs of relationships. The pop star just finished her record-breaking Eras Tour on Dec. 8 and is rumored to drop another project and tour in 2026. Take a look back at some of her exes who inspired some of her famous hits:
“Picture To Burn” – Jordan Oxford (2003/2004)
A freshman high school relationship was the inspiration behind Swift's revengeful “Picture To Burn.” Swift dated Jordan Oxford in her earlier years and wrote the song after he cheated on her with a girl she was friends with named Chelsea. The two ended up getting married later on. While Swift was clearly angry at the time, nearly a decade later, Chelsea and Swift reconciled according to the Daily Mail.
“Fifteen” – Brandon Borello (2005)
The title seemingly gives it away, but Swift spoke about her sophomore high school boyfriend, Brandon Borello, in the song, “Fifteen.” “Our Song” and “Tim McGraw” are also suspected to be about Borello as they speak about teenage love.
“Should've Said No” – Sam Armstrong (2005/2006)
Another high school relationship Swift reportedly had was with a boy named Sam Armstrong. Unlike the fizzled-out relationship she had with Borello, this one had a lot more drama. Armstrong reportedly cheated on Swift which she highlighted in the breakup song “Should've Said No.” He later spoke about the breakup in 2016 on the game show, “To Tell The Truth.”
@theswiftsource Taylor Swift’s high school ex went on a reality show to talk about her #swifttok #swiftie #taylorswift
Forever and Always – Joe Jonas (2008)
Swift and Joe Jonas dated for three months in 2008. They broke up when Jonas called her in a phone call that only lasted less than 30 seconds. She publicly spoke about the incident during an interview with Ellen DeGeneres in 2012.
Other songs about Jonas that fans believe are about him are her 2010 “Better Than Revenge” and “Last Kiss.” Swift's 2012 “Holy Ground,” and “Mr. Perfectly Fine” from her 2021 re-recording of her Fearless album are also rumored to be about the Jonas Brother singer.
Back To December – Taylor Lautner (2009)
Taylor Lautner and Swift dated in the fall of 2009 after meeting during the film “Valentine's Day.” While the two didn't have a long romantic relationship, after years have passed, they now have a friendship. They've even worked together again on her song “I Can See You” where Lautner made a surprise appearance. Swift is even friends with Lautner's wife, Taylor Dome, who he married in 2022.
Dear John – John Mayer (2009 – 2010)
One of Swift's most famous romances was with fellow singer John Mayer. Their relationship began in late 2009 and they broke up around 2010. Their romance was rumored to be referenced in Swift's “Dear John” and Mayer's “Paper Dolls.”
The singers have a rather large age gap, with Swift only being 19 and Mayer 32 at the time. She references their ages with the line “Don't you think I was too young to be messed with?” in the song. Mayer said he was “humiliated” that Swift said that in the song. When asked who the song was about in response to Mayer's reaction. “How presumptuous!” she told Glamour in 2012. “I never disclose who my songs are about.”
“Starlight” – Conor Kennedy (2012)
Swift had a brief romance with Conor Kennedy, son of Robert F. Kennedy Jr. She was introduced to Conor after connecting with his aunt, Rory Kennedy. The singer was 23 years old when she dated Conor, who was 18 at the time. Swift got some backlash due to the age difference between the two.
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The singer's “Starlight” is rumored to be her relationship with Conor and his grandmother, Ethel Kennedy. Fans also believe that “Everything Has Changed” is might be about Conor.
The couple dated most of 2012 but they eventually broke up in October of that year. “It was just a distance thing,” a source told Us Weekly at the time.
“All Too Well” (2012) – Jake Gyllenhaal
While many of Swift's exes may have a song or two written about them, Jake Gyllenhaal has an album. Fans believe that the singer's Red is about Spider-Man: Far From Home actor is the inspiration behind Swift's fourth studio project which was released in October 2012.
The song “All Too Well” which tells about a failed romantic relationship — and a missing scarf — is one of Swift's most famous songs. She made the song a short film starring Dylan O'Brien, Sadie Sink, and herself.
“Left my scarf there at your sister’s house. And you’ve still got it in your drawer even now,” Swift sings on the track.
While the whole album is rumored to be about Gyllenhaal, another favorite is “I Bet You Think About Me,” where she talks about him wearing the scarf.
“Style” – Harry Styles (2012 -2013)
Fresh off her breakup with Gyllenhaal, Swift was not going to let that relationship ruin her chance at being in love. She began dating Harry Styles in November 2012 but it was short-lived when the couple called it quits in the New Year. The song “Style” is rumored to be about the One Direction frontman — I mean, isn't the title obvious?
Swift also was the muse behind two of Styles' songs: “Two Ghosts” and “Ever Since New York.” He mentions “red lips” — her signature lipstick shade — and the title in the latter song is where the singer spends a lot of her off time.
“You're Losing Me” – Joe Allwyn
One of Swift's longest relationships to date is with musician and actor Joe Allwyn. Swift dated Allwyn for six years and ended their relationship in 2023. There was no bad blood between the two but it's rumored that Allwyn struggled with Swift's fame and that the two ultimately “grew apart.”
There are several songs that are hinted to be about her relationship with Allwyn with the main one being “You're Losing Me.” In the song, Swift gets vulnerable about why some traits of hers ultimately led to the end of their relationship.
“And I wouldn’t marry me either, a pathological people pleaser, who only wanted you to see her,” she sings int the song.
“Gorgeous,” is allegedly about the first time Swift saw Alwyn in 2016. “Dancing With Our Hands Tied” is about her social status getting in the way of her relationships –sound familar? However, tracks like “Lover,” and “Paper Rings,” are about her wanting to have a future with Alwyn. Both of them have since moved on with their love life with Swift dating Kansas City Chiefs tight end Travis Kelce and Alwyn keeping his private life, well private.
