All Taylor Swift’s ex-boyfriends and the songs she wrote about them – Wales Online

Some of her biggest hits are inspired by life during her past relationships
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It's key, when it comes to understanding Taylor Swift's lyrics, that she does not just write about love and breakups. She is best-known in the music industry for her sharp storytelling skills, and often uses her own personal experiences as inspiration for her song lyrics.
While she doesn't always confirm which songs are about a specific time, event or person, her fans are notorious for deconstructing her songs and trying to work out exactly what might have influenced the different narratives she chooses to write about. Throughout her career, she has written a variety of songs addressing different topics, from sexism and gender equality with songs such as 'The Man', to the power of letting go of negativity with 'Shake It Off' and wrestling with her insecurities with 'The Archer.'
But one aspect of her lyrics that resonate strongly with people who listen to her music all around the world is how she characterises different tales of romance, heartbreak and navigating life alongside relationships which come with joy, sadness and all things in between to connect with her fans with music- so here are the key people and songs that are thought to have been a part of Taylor Swift's dating timeline, and inter-twined with some incredible songs. For the latest TV & Showbiz news, sign up to our newsletter
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Taylor and Jonas, who is also a singer songwriter were initially dating in secret for a few months in the summer of 2008, at the same time Taylor joined the Jonas Brothers on stage for several concerts during their Burnin’ Up Tour. One of the standout moments for this relationship was when Taylor famously referenced their split on The Ellen Degeneres Show, when she highlighted how he had broken up with her in a 27-second phone call.
Fans believe that the songs from her Fearless album, 'Forever and Always' and her Speak Now anthem 'Better Than Revenge' were both written about the breakup. Swiftdom also generally agrees that the tracks 'Mr. Perfectly Fine' and 'You All Over Me,' from the re-recording of the album 2021's Fearless (Taylor's Version), are about Jonas. Sophie Turner, Jonas' ex-wife, made light of listening to 'Mr. Perfectly Fine' at the time by posting on Instagram; "It's not NOT a bop."
Taylor and her 'You Belong With Me' co-star Lucas Till, who is a well know actor, are thought to have dated briefly in 2009, but it seems it ended with them on good terms, hence why the singer-songwriter appears to have never written about their romance. Till later spoke out about their romantic spell never turned into anything serious because he "really just liked her as a friend."
It is believed that the couple fell for each other while filming Valentine's Day in October and then split up just a couple of months later that December. But there's no bad blood here, as following this- they have both become friends, with actor, Lautner even featuring in Swift's 'I Can See You' video and he made a special appearance at her Eras Tour show in Kansas City.
Taylor and singer songwriter and guitarist John Mayer first connected in 2009, when they collaborated on his single 'Half of My Heart.' The musicians went on to perform together a handful of times, sparking rumours from fans, and although neither of them publicly confirmed the romance, both Swift and Mayer released breakup tracks around that time. These included Swift's 'Dear John' and Mayer's 'Paper Doll' which was believed to be inspired by the relationship. And even though it's been more than 10 years since their romance, fans once again started speculating after the release of her 2022 album Midnights with the track 'Would've, Could've, Should've,' which they believe could be about her relationship with John when she was 19, and he was 32.
Although sparks did not fly for too long with Jake Gyllenhaal, the American actor may have inspired one of most iconic breakup songs Taylor has ever written ('All Too Well'). As with many of her songs, although the singer has never explicitly said the song, which she re-recorded in 2022 and released an extended 10 minute version of, has many lyrics which could be hinting that it is about Gyllenhaal. One key example is how the lyrics of the 'All Too Well' 10-minute version start with her memory of visiting her boyfriend's sister's place. The weather description corresponds with her relationship with Gyllenhaal, which began in October 2010. Maggie Gyllenhaal, who at the time acknowledged that she did had Swift in her home for dinner, may be her lover's sister.
Taylor's relationship with the major activisit Conor Kennedy was initially met with a lot of criticism because at the start of their romance, she was 22 and Kennedy was 18 in 2012. Although she and Kennedy may have only dated for two months, some people believe that he was still referenced in several of Swift's hit songs, including 'Begin Again,' 'Starlight,' and 'Everything Has Changed,' according to Cheat Sheet.
Taylor previously stated to Digital Spy that the song 'Everything Has Changed' is "about realising your life has flipped upside down after falling for someone new," a claim that fans of the song feel was made in reference to Kennedy. The second single from Swift's Red album, which was released in late October 2012, titled 'Begin Again' , Taylor described the song as "what happens on your first date after a horrible breakup" on Good Morning America. Although the "horrible breakup" may have been about any of her ex-boyfriends, many believe the timing implies that the song is about meeting Kennedy.
'Starlight' is though to tell the story of Kennedy's grandmother, Ethel, meeting her husband, and the liner message is what is most indicative of this, reading simply as; 'For Ethel.' For the latest TV & Showbiz news, sign up to our newsletter
Unless you live under a rock, you will likely have heard references to Taylor and pop star Harry Styles' high profile romance at some point, affectionately known by some fans as the internet's "divorced parents." The stars are thought to have met in 2012, at the 2012 Kids' Choice Awards, when Taylor was 22 at this point, and Styles, 18.
But despite the amount of interest surrounding their romance, no one quite knows what went wrong for the duo, who were pictured together on many occasions at the time. It wasn't until Styles began a new phase of his career going solo, in an interview with Rolling Stone, he touched on the complexities of being in a high profile relationship at a young age, he noted: "Relationships are hard, at any age.
"And adding in that you don’t really understand exactly how it works when you’re 18, trying to navigate [fame and media attention] didn’t make it easier. I mean, you’re a little bit awkward to begin with. You’re on a date with someone you really like. It should be that simple, right? It was a learning experience for sure.”
Their romance also led to a string of songs by Taylor that people believe strongly is about life at the time she was with Styles, including the infamous; 'Style', 'Two Ghosts', 'Out of the Woods', 'Say Don't Go', 'Is It Over Now?', 'Now That We Don't Talk', 'I Know Places', 'Wildest Dreams', 'Clean', 'Wonderland', and 'Question…?'
Taylor and singer Calvin Harris reportedly dated for 15 months and had an amicable break up. A highlight of this relationship which also played out largely in the public eye was the way the couple announced they were dating.
While most celebrity couples make their relationship Instagram official with a cute selfie, Harris revealed they had been getting much closer to his followers by posting a since-deleted image of Taylor's cats in April 2015. They were then seen together the next month at the 2015 Billboard Music Awards.
A little after while after their split, Taylor started dating actor Tom Hiddleston and Harris went saying only positives about his ex on social media to going on an X, formerly known as Twitter, spree about their former song collaboration ('This Is What You Came For'). Initially, it seems they had both agreed to keep their work on the song a secret, but this was revealed at a point he was not expecting.
One of the main tracks people assume was written about Harris is Taylor’s song 'I Forgot That You Existed' which is all about the feeling of indifference following the ending of a relationship, from her 2019 album Lover. 'Dancing With Our Hands Tied' from Reputation, is also thought to be about the producer, who once bought her a locket, as this particular song references an invisible locket.
Another song which fans are divided on as to whether it is about him is 'Getaway Car.' This was released in 2017, but some people also think it could be about her later relationship with Tom Hiddleston. In the song, Taylor describes what it is like to escape a difficult relationship and transition into a new one, possibly with Hiddleston, who became the metaphorical vehicle to transport her away from her troubles.
Taylor and actor Tom Hiddleston were first seen together in June 2016, shortly after Taylor's breakup with Calvin Harris, with the pair spotted dancing at the Met Gala, and soon after, they were seen together in lots of different locations. Their relationship was marked by travels, including trips to Rome, Australia, and England.
But their romance seemed fairly short-lived, and they parted ways a few months later. As well as 'Getaway Car' being one of the songs speculated to be about Hiddleston, some fans also believe that the song 'Dress' from Reputation might also reference their relationship. In 'Dress,' Taylor sings about a passionate and intimate connection, which some interpret as reflective of her time with Tom Hiddleston.
Taylor and actor Joe Alwyn spent six years together, after meeting at the MET Gala in 2016. Many fans expected them to go the distance, with lots willing the couple to get married. Joe is thought to have influenced many of Taylor's lyrics, and even co-written some songs with her over recent years.
According to Business Insider, Alwyn cowrote six songs with Taylor on her previous albums: 'Exile' and 'Betty' from the Folklore album in 2020; 'Champagne Problems,' 'Coney Island,' and 'Evermore' from the Evermore album in 2020; and 'Sweet Nothing' from the Midnights album in 2022.
Taylor and Joe reportedly called it quits over "differences in their personalities"- the Mirror reported in 2023. At the time, a source revealed: "They've had rough patches before and always worked things out, so friends thought they would take some time apart but eventually come back together."
Swiftdom assumes that Alwyn is the person who Taylor has written about the most, due to the length of time they were together and the timing of her albums, and songs which came out when they were together. Although lots of fans think that many songs written during their time together are about other tales of love and loss as well as a few anthems to her exes.
Some of the most note-able tracks we can guess might be about the famous actor during their time together include the likes of 'London Boy,' 'Delicate', 'Gorgeous', 'King of My Heart', 'Lover', 'Paper Rings', 'Cornelia Street', 'Invisible String', 'Peace', 'Lavender Haze' and 'Karma'. Since their split, however, there have been several tracks which could also allude to the man lots of swifties thought would be her end game, such as ' So Long London', 'Fresh Out The Slammer', 'loml', 'I Can Do It With A Broken Heart', 'The Albatross', and 'How Did It End?'
Taylor Swift and Matt Healy were rumoured to have a brief romantic connection in the past. Matt Healy, the lead singer of The 1975, and Taylor Swift were seen together in 2014, sparking speculation about a possible relationship. But fast forward to 2023 after Taylor and Alwyn ended things, and the pair seemed to be rekindling their romance as they were spotted spending more and more time together. Healey even flew 17 hours to Nashville to attend one of her shows on her Eras Tour.
But this again seemed to be quite brief, as she got together with Travis Kelce just a few months later. Fans initially speculated that Taylor's latest album, The Tortured Poets Department would document much of her relationship with Alwyn, but there seemed to be many references to her romance with Healy, including songs like ‘The Smallest Man Who Ever Lived’, Fresh Out the Slammer’, ‘I Can Fix Him (No Really I Can),’ and ‘Guilty As Sin?,’ which swifties believe are all about the turbulent time they spent together, which cause great debate due to Healy's controversial reputation.
In the track Fortnight, in which she collaborates with Post Malone, she also sings: "I love you, it’s ruining my life / I touched you for only a fortnight," which also seems to allude to her brief romance with Matt, which is now thought to have only lasted for two weeks.
According to the Mirror, the three-time Super Bowl Champ Travis Kelce expressed his interest in Taylor after attending one of her Eras Tour shows, with him failing to give her his number on a bracelet he had made. He spoke on a podcast he co-hosts, noting: "If you're up on Taylor Swift concerts, there are friendship bracelets and I had received a bunch of them, but I wanted to give Taylor Swift with my number on it." He added: "She doesn't meet anybody, or at least she didn't want to meet me, so I took it personal."
But things seem to have worked out for them, as the couple then went public with their romance in September, and have been picture lots of times looking happier than ever to celebrate their romance despite the fact the world is watching so closely. Taylor has been seen supporting Travis at lots of his football games, and Travis in the crowd many times at her Eras Tour shows.
The song "The Alchemy," from her latest Tortured Poets Department album release seems to make references to the American football player's "touch downs," and a serenade for Kelce.

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