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For years, while we’ve been belting out Taylor Swift’s eerily-similar-to-our-own-life breakup anthems, the country crooner turned pop star has successfully dated a slew of Hollywood heartthrobs.
The ‘Midnights’ singer has been linked to musicians and movie stars alike and has a penchant for memorialising her fallen relationships in lyrical form. Most recently, Taylor has been linked to Kansas City Chiefs NFL player, Travis Kelce (more on that below).
From Jake Gyllenhaal to John Mayer, see every lucky guy who has dated Taylor Swift since she came into the spotlight following her debut album Fearless.
Here’s a look, in order, of all the men Taylor has dated, and which of her songs are about the romance.
Joe Jonas (2008)
Taylor dated the former Jonas Brother and now lead frontman of DNCE from July 2008 to October 2008. This was Taylor’s first public breakup, and possibly most brutal being that Joe decided to do the heartbreaking over a 27-second phone call. The country crooner’s songs “Last Kiss” and “Forever and Always” are believed to have been written about her breakup with Jonas, while “Holy Ground” is a later, more positive perspective on the short-lived romance.
Jonas later married Sophie Turner, and the pair split in 2023.
Lucas Till (2009)
Taylor and Hollywood heartthrob Lucas Till dated for only a matter of months in 2009, after Lucas played the next-door neighbour in Taylor’s “You Belong With Me” music video. Lucas later spoke out about the two’s brief attempt at dating, stating that at the end of the day, they were better as friends.
“We dated for a little bit. But, there was no friction because we were too nice,” he told MTV. “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.”
Taylor Lautner (2009)
Who could forget the Taylor/Taylor romance of 2009? The two met when they co-starred as high school sweethearts in the romantic comedy Valentine’s Day. Taylor’s song “Back To December”—where she sings: “Your tanned skin, your sweet smile”, on top of an apology for a rough night in December—is about ex Taylor Lautner, and the night she dumped him.
John Mayer (2009)
“It made me feel terrible because I didn’t deserve it,” Mayer told Rolling Stone in a 2012 interview. “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.” Later, Mayer responded musically with his song ‘Paper Dolls’ on his 2013 album Paradise Valley. “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,” he sings.
Cory Monteith (2010)
Though Taylor and the Glee star never officially confirmed they were dating, the two were photographed together on many occasions. Taylor also clearly blushed when asked if the two had dated on The Ellen DeGeneres Show. On the day of Cory’s tragic death in July 2013, Taylor tweeted: “Speechless. And for the worst reason.”
Jake Gyllenhaal (2010-2011)
One of Taylor’s most public relationships, the couple were regularly seen out in New York City and Los Angeles. Rumour has it the couple’s 10-year age gap just wasn’t working so Jake called it quits. “The Last Time”—with lyrics “Put my name at the top of your list”—is said to be about this romance.
“All Too Well” which documents the infamous scarf situation, is also about Gyllenhaal. This song references a number of details specific to their relationship, including a car trip to upstate New York and a Thanksgiving dinner at Maggie Gyllenhaal’s house.
In the first verse, Swift makes this fascinating claim: “Left my scarf there at your sister’s house. And you’ve still got it in your drawer even now” to the dramatic end “Now you mail back my things and I walk home alone, But you keep my old scarf from that very first week ‘Cause it reminds you of innocence and it smells like me.” Gyllenhaal has been photographed in years since wearing Taylor’s scarf, much to the amusement and confusion of Swift fans.
Adam Young (2011)
Owl City’s Adam Young never officially dated Taylor, with things never escalating past some emails and one face-to-face meeting. Taylor was so excited to meet Young that she later wrote the song “Enchanted” about him.
She sings: “All I can say is it was enchanting to meet you”. Young later released a cover version of Taylor’s song “Enchanted” on Valentine’s Day when he realised the song was about him.
Chord Overstreet (2011)
Taylor and Chord reportedly only went on one date, but there are pictures from the event so naturally, he makes the list.
Eddie Redmayne (2011-2012)
It is rumoured that Taylor and Eddie started dating when she auditioned for the part of Eponine in Les Miserables. They were seen together a lot in New York while the auditions were taking place. Unfortunately, Eddie’s captivating green eyes and freckles didn’t make enough of an impact to earn a tribute track.
Zac Efron (2012)
Once Disney’s High School Musical teenage stud, Zac has been making our hearts skip for years prior to his run-in with Tay. The two reportedly started dating for a few months while promoting their movie The Lorax. However, the two have both denied the relationship.
The pair even went as far as to write a song together rejecting the dating rumours through a parody of Foster the People’s “Pumped Up Kicks” on The Ellen DeGeneres Show. We can still dream though.
Conor Kennedy (2012)
Taylor dated Robert F. Kennedy’s grandson Conor Kennedy during the summer of 2012. She did receive some criticism for the age difference in the relationship, being that she was 22 and Conor was 18. Taylor even purchased a home near the Kennedy compound in Hyannis Port, Massachusetts, during the romance. It started to look like things between Taylor and Conor weren’t going so well when his family accused the singer of crashing the wedding of Conor’s cousin Kyle in August. Her reps denied it, but it appeared the damage had been done.
“Begin Again” has been linked to Conor, especially the lyric: “I think it’s strange that you think I’m funny ’cause he never did.”
Harry Styles (2012-2013)
One of Taylor’s most divisive relationships to date. The couple, despite only dating for a month, shared paper aeroplane necklaces, strolled through Central Park, kissed in Times Square on New Year’s Eve and even got in a snowmobile accident.
“I Knew You Were Trouble” is about the One Direction heartthrob. Taylor’s album 1989 is also filled with subtle references to Harry Styles, especially “Out Of The Woods” with its lyrical references to their December romance and the accident, and “Style” which is fairly self-explanatory.
Calvin Harris (2015-2016)
Taylor and Harris shared a fairly long romance and was her most well-documented. The couple would regularly appear on red carpets together and post images to their social media pages. Multiple reports claim that it was Calvin who wanted to break up.
While neither have ever commented on it, Taylor’s hit “We Are Never Ever Ever Getting Back Together” was presumed to be about Calvin. However, many Swift fans remain confident this is about Gyllenhaal.
Tom Hiddleston (2016)
Tom Hiddleston and Taylor Swift, better known as Hiddleswift, was the love story that shocked the globe. The couple met in New York and then took their romance on the road (Rhode Island, Italy, Australia, and England to name a few stops).
But sadly, all good things must come to an end. Just two months after Hiddleston was photographed in an ‘I Heart T.S.’ t-shirt, the couple would call it quits.
Joe Alwyn (2017-2023)
Actor Joe Alwyn was Taylor Swift’s longest relationship to date, with the couple keeping their romance well out of the public eye. They were first photographed together in 2017, enjoying coffee on a balcony in Nashville, and dated for six years before reports emerged in April 2023 they had broken up a few weeks earlier.
One song ‘…Ready for It?’ has fans divided over whether it’s about Joe or her former love interest Harry Styles. But, according to BuzzFeed, Taylor reportedly liked a Tumblr post breaking down the lyrics, with all signs pointing to them being about Joe. Taylor’s song ‘Gorgeous’ is definitely about Joe, with lyrics: “You make me so happy, it turns back to sad.”
Fans also picked up on a song from Reputation, named Dress which appeared to reference the first time she met Alwyn with lyrics referring to two lovers meeting while one’s hair was bleached. At the 2016 Met Gala, Swift had bleached blonde hair, and it’s been rumoured the pair crossed paths that night.
The pair even collaborated on Taylor’s lockdown albums, Folklore and Evermore, with Alwyn credited as “William Bowery”. During her Folklore: The Long Pond Studio Sessions film, Taylor explained: “I was like, ‘Hey, this could be really weird and we could hate this [but] because we’re in quarantine and there’s nothing else going on, could we just try to write this song together?’”
In 2019, the pair sparked engagement (and even wedding) rumours when her album Lover alluded to marriage, but neither party confirmed nor denied the rumour. In early 2022, Alwyn actually spoke about the rumours by providing an answer to the Wall Street Journal that told us precisely nothing: “If I had a pound for every time I think I’ve been told I’ve been engaged, then I’d have a lot of pound coins. I mean, the truth is, if the answer was yes, I wouldn’t say, and if the answer was no, I wouldn’t say,” he told the publication.
Sadly, in April 2023, news emerged the couple had amicably called it quits. A source told ET that “it was not dramatic” and that “the relationship had just run its course. It’s why [Alwyn] hasn’t been spotted at any shows.”
The end of an era, as Ms Swift herself would say.
Since then, Taylor has released break up song ‘You’re Losing Me’, detailing the break up in her own words. It suggests that the relationship ran its course, with the man in the song (presumed to be Alwyn) not wanting to marry her. “And I wouldn’t marry me either, a pathological people pleaser, who only wanted you to see her,” she sings.
Matty Healy (2023)
After departing her six year relationship with Joe Alwyn, Taylor appeared to quickly start up a new relationship with Matty Healy.
The Sun first reported the relationship on May 3, suggesting that Healy would be present at Taylor’s Nashville shows to prove the relationship was real.
“It’s super-early days, but it feels right. They first dated, very briefly, almost ten years ago but timings just didn’t work out,” a source told the publication. “Taylor and Joe actually split up back in February, so there was absolutely no crossover.”
Then, on May 5, Healy was spotted at Swift’s show in Nashville. He attended every show in the city, even performing on stage with Swift’s support act Phoebe Bridgers. On May 6 they were seen in a car together and by May 8, Entertainment Tonight was reporting that the two had been set up by Swift’s producer Jack Antonoff.
On May 11 the couple were allegedly seen holding hands out in New York, and on May 15 Healy was spotted at Taylor’s hometown show in Philadelphia, alongside her father Scott Swift. The couple were deemed ‘official’ when they were seen leaving Taylor’s party at Electric Lady Studios in the West Village in New York City together, with Healy’s hand on the small of her back.
Fans have been perplexed by Swift’s choice in Healy, given he has garnered controversy over the years as the front man for rock band The 1975.
However, it seems Swift is smitten with the situation. On May 21, she told fans at at Gillette Stadium in Foxborough, Massachusetts on her Eras Tour, “I kind of feel like telling you, I don’t know, I’ve just never been this happy in my life in all aspects of my life ever before.
“And I just want to thank you for being a part of that. It’s not just the tour. I just sort of feel like my life finally feels like it makes sense.”
Travis Kelce (September 2023)
Kelce, 33, first spoke about being interested in Taylor on his podcast, New Heights, where he revealed he made her a version of the Eras Tour friendship bracelets with his phone number.
Since then, however, a relationship between to the two has become extremely obvious—with Taylor attending a number of Travis’ games, and the two even holding hands in front of paparazzi.
Read their full relationship timeline here.
This article was published by the team at ELLE Australia.
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