Taylor Swift's Dating History: A Timeline of Her Most Famous Relationships

Taylor Swift
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The singer once famously sang that she has a 'long list of ex-lovers.' Here's a look back at her most famous relationships.

No one writes a breakup song quite like Taylor Swift. The country singer turned pop star has an unparalleled talent for tackling the good, the bad and the ugly of real-life love and, as she sings on her 2014 album, 1989, she's "got a long list of ex-lovers" for inspiration. 

That list of ex-lovers in question is also about as star-studded as they come -- one might even call it "Bejeweled." Joe Jonas, Calvin Harris, Harry Styles and Joe Alwyn are just some of the names the GRAMMY winner has dated during her multi-decade career. 

Despite a surplus of fan theories, Swift, 33, is actually quite private about her lyrical inspirations. She never names names, rarely confirming whether or not certain songs are fiction or fact. Nevertheless, fans love to play guessing games, using her lyrics as puzzle pieces for Swift's series of high-profile romances.

These theories are often reignited by Swift's re-releases of her early discography while she works to reclaim ownership of her first six albums (her previous record label's new executive, Scooter Braun, infamously refused to sell the masters to her in 2020). After her release of Red (Taylor's Version) in 2021, many folks online placed intense attention on Swift's ex, Jake Gyllenhaal, the rumored subject of Swift's fan-favorite song, "All Too Well," and its accompanying 10-minute version. Gyllenhaal was 29 when he dated then 20-year-old Swift in 2010. 

Last week, Swift's release of Speak Now (Taylor's Version), originally from 2010, pushed many fans to re-enter debates about the singer's alleged references to her ex, John Mayer, perhaps most notably on the track "Dear John." Mayer was 32 when he dated then 19-year-old Swift in 2009. 

Swift addressed the growing internet buzz about Mayer at a recent Eras tour performance, when she asked her fans to practice kindness ahead of her re-recording's release. 

"I’m 33 years old, I don’t care about anything that happened to me when I was 19 except the songs I wrote," she told the crowd. "So what I’m trying to tell you is that I'm not putting this album out so that you could go and should feel the need to defend me on the internet against someone you think I might have written the song about 14 billion years ago."

Here's ET's Lover look back at Swift's most famous relationships. 

2008: Joe Jonas 

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Joe Jonas and Swift dated for just a few months in the summer of 2008, but their relationship has since lived in infamy after Swift said during an appearance on The Ellen DeGeneres Show that her ex had ended things via a 25-second phone call. Speak Now's "Last Kiss" and "Better Than Revenge" (2010) and Fearless' "Forever and Always" (2008) are both said to be about the breakup. Fans also speculate that Red's "Holy Ground" (2012) is a reference to her 2008 performance with the Jonas Brothers. 

Swift later told DeGeneres that she regretted her original remarks about Jonas' breakup with her. "That was too much, that was too much," she said during a 2019 appearance on the show. "I was 18...we laugh about it now, but that was mouthy, yeah, some teenage stuff there." Jonas later said he appreciated the apology, too. "It did feel nice," he said several weeks later on ITV's Lorraine show. "It's something that I was probably feeling pretty bad about when I was younger, but, at the end of the day, I've moved on. I'm sure Taylor's moved on. It feels nice. We're all friends. It's all good. We were so young." 

2009: Taylor Lautner 

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Swift dated Twilight star Taylor Lautner from October to December 2009, around the same time that they co-starred as high school sweethearts in Garry Marshall's romantic comedy, Valentine's Day. Swift's much-beloved song, "Back to December," from 2010's Speak Now, is allegedly an apology to Lautner revolving around the night she broke up with him. 

Swift and Lautner have since become good friends. Following her release of Speak Now (Taylor's Version), Lautner starred alongside Joey King and Presley Cash in a music video for Swift's vault track, "I Can See You." Swift debuted the video during a performance at the Eras tour in Kansas City, where Lautner, King and Cash joined the singer onstage following its premiere. 

"Taylor, I respect you so much," Lautner told Swift after backflipping onto the stage. "Not just for the singer you are, the songwriter, the performer, but for the human you are. You are gracious, humble, kind and I am honored to know you."

2009: Lucas Till 

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Lucas Till briefly dated Swift after starring as her next-door neighbor in the 2009 music video for "You Belong With Me." Till also starred as Travis Brody in 2009's Hannah Montana: The Movie. His relationship with Swift only lasted a few months because according to Till, the pair was better off as friends. 

"We dated for a little bit. But there was no friction because we were too nice," he told MTV that same year. "We just really both liked each other… [but] most relationships work out 'cause you get along and then you don't, and then you make up and it's passionate, and with us, I really just liked her as a friend. That's the only reason that didn't work out."

2009-10: John Mayer

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John Mayer and Swift were romantically linked from late 2009 to early 2010, when Swift was 19 and Mayer was 32. Swift's 2010 Speak Now track, "Dear John," is the singer's most infamous alleged reference to the much-discussed relationship. A trio of especially cutting lines read, "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." 

Swifties are often fervent in their dislike of Mayer, both for the couple's drastic age difference and for theories about Mayer's alleged treatment of Swift based on her lyrics. Mayer later complained to Rolling Stone about "Dear John," saying the track made him "feel terrible," explaining, "I didn't deserve it. I'm pretty good at taking accountability now, and I never did anything to deserve that. It was a really lousy thing for her to do."

Swift addressed her fans' distaste for Mayer at a recent Eras tour performance, when she asked Swifties to practice kindness ahead of her re-recording of Speak Now

"I’m 33 years old, I don't care about anything that happened to me when I was 19 except the songs I wrote," she told the crowd. "So what I'm trying to tell you is that I'm not putting this album out so that you could go and should feel the need to defend me on the internet against someone you think I might have written the song about 14 billion years ago."

2010-11: Jake Gyllenhaal 

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Swift and Jake Gyllenhaal were in an on-again/off-again relationship from October 2010 into early 2011, when Swift was 20 and Gyllenhaal was 29. Fans believe several of the songs on Swift's 2012 album, Red, are about her relationship with Gyllenhaal, including lead single "We Are Never Getting Back Together" and the power ballad, "All Too Well." 

When Swift released Red (Taylor's Version) in 2021, she also recorded her original 10-minute draft of "All Too Well," this time titled "All Too Well (10 Minute Version) (Taylor's Version) (From The Vault)," which further details an exploitative relationship between a young woman and an older man who many fans still believe to be Gyllenhaal. The new version of the song quickly landed at No. 1 on the Billboard Hot 100, her eighth song at the time to reach such status. Swift also subsequently released a short film featuring the track starring Dylan O'Brien and Sadie Sink, and later that week performed the 10-minute number on Saturday Night Live

Gyllenhaal turned off his Instagram comments around the time of Red (Taylor's Version)'s release, leading many to assume he was facing an onslaught of personal attacks in response to the album. He later told Esquire that he did not resent Swift for her release of the extended "All Too Well," alleging the song "has nothing to do with me." 

"It's about her relationship with her fans. It is her expression. Artists tap into personal experiences for inspiration, and I don't begrudge anyone that," he said. 

2012: Conor Kennedy 

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Swift dated Conor Kennedy, grandson of Robert F. Kennedy, during the summer of 2012. At the time, Swift's love of the Kennedy family was well-documented, including one 2011 Rolling Stone interview in which the singer said she had just finished "a 900-page book called The Kennedy Women, which dates back to the lineage of the first Kennedys coming from Ireland in the 1800s."

Swift met Kennedy through her connections with his aunt, Rory Kennedy. Many fans believe her song, "Begin Again," from 2012's Red, is about the start of Swift's relationship with Kennedy following her breakup from Gyllenhaal. 

2012-13: Harry Styles 

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Pop star and former One Direction singer Harry Styles dated Swift from October 2012 to January 2013. Before they made their relationship official, some fans believe Swift wrote her Red track, "I Knew You Were Trouble," about a fling with Styles earlier in 2012. Following their split, many believe tracks "Out of the Woods," "Style," "All You Had to Do Was Stay," "I Wish You Would," "How You Get the Girl," "This Love," "I Know Places," "Clean" and "Wonderland" -- all from Swift's 2014 album, 1989, are about Styles. Off her 2022 album, Midnights, many also posit that the songs "Maroon" and "Question..." are about him as well. 

In 2020, Styles told Howard Stern he was ultimately happy to be the subject of any of Swift's songwriting. "I think about what it means to me to write a song about somebody else and for somebody else to do that, it's, like, flattering. Even if the song isn't that flattering, you still spent time on it and ultimately, using Taylor as an example, she's a great songwriter. So at least they're good songs," he said.

2015-16: Calvin Harris 

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Swift and Scottish DJ Calvin Harris, real name Adam Wiles, dated for 15 months between 2015 and 2016, eventually breaking things off in March 2016. 

By June of that year, Swift had begun dating British actor Tom Hiddleston, and she Swift and Harris had wiped all record of their relationship from their respective social media accounts.

In July, Swift's rep told People that the singer had written Harris' song, "This Is What You Come For" featuring Rihanna, under the pseudonym Nils Sjoberg. The revelation came after Harris said in an interview he couldn't see collaborating with his then-girlfriend. 

"You know, we haven't even spoken about it. I can't see it happening, though," Harris said while promoting the song, seemingly contradicting his work with Swift on the track. Reports later surfaced that Swift had been hurt by his comments, and that the disagreement led to the end of their relationship. 

Soon after the news broke, Harris commented about the situation on Twitter, where he initially praised his ex for her music skills before then taking a turn for the negative. "And she sings on a little bit of it too. Amazing lyric writer and she smashed it as usual," he wrote. "I wrote the music, produced the song, arranged it and cut the vocals though. And initially she wanted it kept secret, hence the pseudonym."

Harris later told British GQ, "It's very difficult when something I consider so personal plays out very publicly. The aftermath of the relationship was way more heavily publicized than the relationship itself. When we were together, we were very careful for it not to be a media circus. She respected my feelings in that sense."

Many fans believe Swift's 2017 track, "Dancing With Our Hands Tied," from her Reputation album, and 2019's "I Forgot That You Existed," from Lover, are both about Harris. 

2016: Tom Hiddleston 

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Swift briefly dated British actor Tom Hiddleston during the summer of 2016, after the two were first spotted together at the Met Gala a few days before Swift's breakup with Harris. Later, Swift and Hiddleston were seen kissing on a beach in June 2016, and Hiddleston wore his now-iconic "I ♥ T.S." tank top at Swift's Fourth of July beach bash.

By September, however, ET had confirmed the couple's breakup. "It was an amicable split," the source said. Though the relationship was short-lived, many allege that Swift's hit song, "Getaway Car," off 2017's Reputation, is about the couple's whirlwind romance. 

2016-23: Joe Alwyn 

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Swift's relationship with British actor Joe Alwyn was perhaps the one she kept the most private, with very little PDA and no Instagram or red carpet appearances. Though it's unclear when the couple started dating, Swift insinuated in a since-deleted 2022 Instagram post that the couple had been together for six years. 

Fans believe much of Swift's recent discography was inspired by her relationship with Alwyn, including tracks from Reputation (2017), Lover (2019), Folklore (2020), Evermore (2020) and Midnights (2022). Alwyn also boasts an impressive number of co-writing credits, under the pseudonym William Bowery, on albums Folklore, Evermore and Midnights

On April 8, 2023, shortly after the launch of Swift's Eras Tour, ET confirmed that the two had ended their relationship. ET also learned that the split was amicable and "not dramatic."

"The relationship had just run its course. It's why [Alwyn] hasn't been spotted at any shows," the source said.

2023: Matty Healy 

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The 1975 singer Matty Healy was first linked to Swift when he was spotted at the Nashville stop of her Eras Tour in May 2023, one month after news of her breakup from Alwyn first broke. The duo, who have been longtime friends, was later photographed together as well. 

"Taylor and Matty like each other," a source told ET shortly thereafter. "Taylor has a crush on Matty and they are having a good time hanging out. Matty also thinks Taylor is awesome and incredibly talented, too. They dated briefly in the past."

By June, though, the romance had ended. "Taylor and Matty broke up," a source told ET. "They are both extremely busy and realized they're not really compatible with each other. Taylor's friends want what's best for her and aren't shocked that their relationship fizzled out since she recently got out of a long-term relationship."