Taylor Swift’s Dating History: A Timeline of Her Famous Exes and Flings

The Disney heartthrob ended their relationship in a 27-second phone call in October 2008. “That’s got to be a record,” Swift told Ellen DeGeneres. “When I find the person who’s right for me, he’ll be wonderful. I’m not even going to remember the boy who broke up with me over the phone.” After Jonas welcomed his first child with Sophie Turner in July 2020, fans speculated whether Swift sent the couple a baby gift based on possible easter eggs in her song “Invisible String.” That lyric in question says, “Cold was the steel of my axe to grind / For the boys who broke my heart / Now I send their babies presents.”

After releasing “Mr. Perfectly Fine” from her vault in April 2021, Swift sparked speculation that the track was written about her 2008 romance with Jonas. “But that was when I got to know Mr. ‘Change of heart,’ ‘Mr. Leaves me all alone,’ I fall apart / It takes everything in me just to get up each day / But it’s wonderful to see that you’re okay,” she sings. Many fans pointed out that the song could be referencing Jonas since he used the phrase “change of heart” to describe their split. Turner later complimented Swift on the song, writing via her Instagram Story, “It’s not NOT a bop,” to which the songstress replied, “Forever bending the knee for the [queen] of the north.”

The Valentine’s Day paramours dated for three months in 2009. “It wasn’t really developing into anything, and wasn’t going to, so they decided they were better as friends,” a source told Us after their December split. “There was no chemistry.”

After starring in Swift’s “You Belong With Me” music video in 2009, the X-Men: Days of Future Past star admitted he had a crush on the singer “since he was 16.” Months later, Till told MTV the pair had dated, but there was “no friction.” “Most relationships work out cause you get along and then you don’t,” the then-19-year-old said. “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.”

Swift was spotted hanging with the Glee star — who once told Us that she was his celebrity crush — at Pinz Bowling Alley in March 2010. The two also spent time together at a January Grammy party and shared a late-night dinner in February 2011. “They seemed really happy,” a source said. Monteith tragically passed away in July 2013.

After a whirlwind two-month romance, multiple sources told Us Swift was completely blindsided whenGyllenhaal dumped her just before New Year’s in 2010. “Jake just told her it wasn’t working out,” one insider said. “Taylor is really upset and hurt. She feels really burned by him.”

Some fans think that Swift’s “Mr. Perfectly Fine” April 2021 vault release was written about the actor following the pair’s short-lived romance. “Hello, Mr. ‘Perfectly fine’ How’s your heart after breaking mine? / Mr. ‘Always at the right place at the right time,’ baby,” the Pennsylvania native sings in the chorus. “Hello Mr. ‘Casually cruel,’ Mr. ‘Everything revolves around you’ / I’ve been Miss ‘Misery’ since your goodbye and you’re Mr. ‘Perfectly fine.’” Fans pointed out that “casually cruel” was also used in Swift’s 2012 hit, “All Too Well,” which is believed to be about Gyllenhaal.

Following Swift’s rerelease of Red (Taylor’s Version) in November 2021, the short film accompanying the 10-minute version of “All Too Well” quickly had people talking. With Sadie Sink and Dylan O’Brien playing the leads, fans pointed out that their respective ages mirrored Swift and Gyllenhaal’s during their brief romance.

Swift — who is pals with the Glee star’s brother, Hot Chelle Rae’s Nash Overstreet — “reached out to Chord,” an insider told Us. The two hit an L.A. Kings NHL home game in February 2011, where a source added, “after the event, Taylor and Chord grabbed a bite. He’s into her.”

Though the two enjoyed a two-hour dinner at Nashville Bistro Cabana in January 2010, a full-fledged romance never developed. Did Swift mind the romance speculation? “I try not to be a complainer, you know?” she told Us. Mayer went on to date Katy Perry on and off, who then inspired Swift’s “Bad Blood,” a track about a frenemy female celeb.

In March 2021, Mayer seemingly responded to Swifties who were trolling him on TikTok, with one user telling him, “You’re not safe here john,” 10 years after the couple split. “POV: You’re berating me and I’m hearing you out,” he captioned a clip of himself nodding his head as he pretended to be lectured by Swift’s fans.

Swift penned an unrequited love song (“Enchanted”) about the Owl City singer in late 2010. After the two exchanged emails, Young wrote Swift his own love song on Valentine’s Day. “Everything about you is beautiful,” he wrote. “You are a true princess from a dreamy fairy tale.”

The Oscar winner was caught flirting with the “Shake It Off” singer in 2012. Swift met the British actor when they were both auditioning for the film adaptation of Les Miserables, and she reportedly fell hard for Redmayne. After a brief fling, however, Redmayne called it off when Swift lost out the role of Eponine to Samantha Barks. Sources said the actor didn’t want to embark on a long-distance romance.

Credit: Robert Button/Wenn.com

Conor Kennedy

Hanging with the Kennedys! In 2012, a 22-year-old Swift started dating Robert F. Kennedy’s then 18-year-old grandson Conor. The duo was continually caught showing major PDA on and around the Kennedy compound in Hyannis Port, Massachusetts, leading Swift to purchase a rumored $4.9 million home nearby. When the three-month romance fizzled in September, Swift quickly moved out — she sold the house in March 2013.

After months of speculation, the One Direction heartthrob was first spotted out with Swift at the Central Park Zoo in December 2012. The romance was short-lived, as a blow-up fight during a holiday getaway led to a split in early 2013. Swift fans have Styles to thank, though, for basically the entirety of the 1989 album, which was reportedly inspired by the Brit.

The exes proved they are on friendly terms in March 2021 while attending the Grammys. The “Watermelon Sugar” singer reunited with Swift at the awards show and shared an animated conversation between commercial breaks. The “Bad Blood” singer was later seen clapping for Styles when he won Best Pop Solo Performance and the English crooner returned the favor when Swift took home the trophy for Album of the Year.

Swift met the Scottish DJ backstage at the 2015 Brit Awards and made it official on March 6, 2015. “I’m in a magical relationship right now. And of course I want it to be ours, and low-key,” she told Vogue in April 2016. “This is the one thing that’s been mine about my personal life.” Two months later, Us confirmed that Harris split from the pop star after 15 months of dating. “It just wasn’t working anymore. She’s OK,” a source told Us.

Not long after their breakup, she began dating Tom Hiddleston. The exes then began feuding after Swift’s team revealed that she helped create Harris’ hit “This Is What You Came For.” While the producer confirmed Swift’s involvement, he called her and her team out across multiple tweets for making him “look bad.”

Two weeks after her split from Harris, Swift was spotted kissing the Thor actor in Rhode Island. “They were all over each other — hugging and kissing — even though there were 20 people coming and going on the beach,” an eyewitness told The Sun in June 2016. “They looked like any young couple madly in love without a care in the world.” Three months later, Hiddleswift met their end, with a source telling Us that the musician “was the one to put the brakes on the relationship.”

In May 2017, word got out that the “Gorgeous” songstress had been dating the British actor — for months! Swift had allegedly been stepping out in London wearing disguises to keep their relationship on the down-low, and even went as far as renting a London pad to be close to her man. The couple are still going strong, with their close pals even placing bets on when they will get engaged. “Taylor’s friends are all talking about a proposal and how she really wants to marry Joe,” an insider exclusively told Us in March 2019. “He’s her dream guy.” A second source told Us in August 2020 that the couple have “discussed children” already and Swift is “very excited about that chapter of her life when the timing is right.” In April 2023, however, the couple split after six years together.

Sources exclusively revealed to Us that Swift spent time with The 1975 frontman in late 2014. Swift met Healy backstage at one of his band’s concerts, and the two hit it off. After Healy was snapped wearing a 1989 album T-shirt during a concert, Swift stepped out with a shirt repping The 1975. The Brit admitted to Australian radio show Shazam that the pair had exchanged numbers, saying “I mean, bloody hell, what am I going to do? Go out with Taylor Swift? …I wouldn’t say no!”

Nearly a decade later, Healy was spotted supporting Swift during her Eras Tour gigs in Nashville. A source exclusively told Us in May 2023 that the musicians were “having a good time reconnecting again” and hoped “to give things a second chance” after their “brief” fling years prior.

The pair called it quits one month later, Us confirmed, with a source explaining that the two “had fun together, but it was never serious.”

After attending the 2023 Eras Tour in July, the Kansas City Chiefs tight end confessed he wanted to give Swift a friendship bracelet with his phone number on it but ultimately didn’t get the chance. Rumors began to swirl that the pair started to connect.

Kelce even invited Swift to come watch him play at some point in the future. The following September, Swift was spotted at a Chiefs game in Kelce’s family suite cheering alongside his mom, Donna Kelce. Following the Chiefs’ victory, the pair left the game together and photos on social media showed them driving off together in a convertible.