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Taylor Swift has a very public dating history. Well, kind of – the artist actually keeps her relationships fairly low-key, but given she has a talent for articulating the nuances of heartache and longing in her music (and loves an lyric with allusion) we feel like we know a lot about her past relationships.
We don’t – not really – but with love-and-loss songs like ‘Red’, ‘Out Of The Woods’ and ‘Getaway Car’ hinting at private moments between the star and her famous ex’s, we’ve naturally become pretty obsessed with who Taylor Swift is dating at any one time.
Swift has been loved-up with current boyfriend Joe Alwyn for years, but if you’re a fan of the artist’s music, it’s worth knowing who she’s (allegedly) singing about. Let’s take a look back at the dating history of Taylor Swift.
Joe Jonas: 2008
Taylor Swift’s earliest known relationship was with fellow music artist Joe Jonas. Both major stars at the time, Jonas was Hollywood’s most eligible bachelor – but the pair only dated for a few months.
Swift’s track ‘Forever And Always’ had long been rumoured to be about Joe Jonas, and the singer confirmed it during her 2009 monologue on Saturday Night Live. ““You might think I’d bring up Joe, that guy who broke up with me on the phone. But I’m not going to mention him in my monologue,” she said at the time.
A searing breakup song, which has lines like “I hold onto the night/you looked me in the eye and told me you loved me/were you just kidding?” Ouch.
However, a line in Swift’s song ‘invisible string’ from 2020 hints at Jonas and his wife, Sophie Turner, implying its all water under the bridge. “Cold was the steel of my axe to grind/For the boys who broke my heart,” she sings. “Now I send their babies presents.” Jonas and Turner welcomed their first child, Willa, in mid-2020.
Lucas Till: 2009
The handsome star of the music video for ‘You Belong With Me’, Lucas Till and Taylor Swift dated for a few months after meeting on set, according to the actor.
He told MTV, “We dated for a little bit. But there was no friction because we were too nice… 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
An iconic pairing of two famous Taylors happened in 2009, when Taylor Lautner of Twilight fame dated Taylor Swift. Their romance was short-lived, and Swift’s some ‘Back To December’ is rumoured to be about the actor. The song is about longing, with lyrics like “So this is me swallowin’ my pride/Standin’ in front of you sayin’ I’m sorry for that night/And I go back to December all the time.”
He addressed the rumours in a Time interview, saying “That’s just what she does.”
John Mayer: 2010
Easily Taylor Swift’s most controversial relationship was her 2010 romance with John Mayer. After the artists collaborated on Mayer’s track ‘Half Of My Heart’, Swift and Mayer’s working relationship turned romantic. At the time, John Mayer was 32 and Taylor Swift 19.
Later, she released the track ‘Dear John’, which called out Mayer for playing her. “Dear John, I see it all, now it was wrong/Don’t you think nineteen is too young/To be played by your dark twisted games, when I loved you so?”
Mayer then spoke to Rolling Stone, saying the track “humiliated” him. “I will say as a songwriter that I think it’s kind of cheap songwriting. I know she’s the biggest thing in the world, and I’m not trying to sink anybody’s ship, but I think it’s abusing your talent to rub your hands together and go, ‘Wait till he gets a load of this!’ That’s bullsh*t.”
In 2022 Swift released ‘Would’ve, Could’ve, Should’ve’, which references a man she dated when she was 19. Fans assume the man in question is John Mayer, and the song details a relationship where innocence is lost, with lyrics like “Give me back my girlhood, it was mine first.”
Cory Monteith: 2010
Cory Monteith and Taylor Swift were a very short-lived item, dating for only a month or so sometime after her split from John Mayer. Still, her relationship with the Glee star is rumoured to have been immortalised in song – he is allegedly the man Swift sings about in ‘Mine’. Although the track is about a long-term love story, Swift explained the story is really about meeting someone who makes you want to settle down.
“I think I’ve developed this pattern of running away when it comes time to fall in love and stay in a relationship,” she told fans during a uStream chat in 2010. “The song is sort of about finding the exception to that and finding someone who would make you believe in love and realise that it could work out, because I’m never ever going to go past hoping that love works out.”
When Monteith tragically died in 2013, Taylor Swift tweeted “Speechless. And for the worst reason.”
Jake Gyllenhaal: 2010
Aside from Harry Styles (we’ll get to him later), the relationship between Taylor Swift and Jake Gyllenhaal has inspired the most famous tracks from the artist. But actually, the couple were only together for a few months in 2010.
This was Swift’s first completely public love story, with paparazzi taking snaps of the couple out for a walk in New York. It’s rumoured that the couple’s ten-year age gap was the demise of their relationship, as fans have pieced together lyrics from the song ‘All Too Well‘, widely assumed to be about Gyllenhaal.
In the song’s 2022 re-release, Swift added extra lyrics that gave more (rumoured) insight into their short-lived love story. “You said if we had been closer in age maybe it would have been fine/And that made me want to die/The idea you had of me, who was she?/A never-needy, ever-lovely jewel whose shine reflects on you.”
Connor Kennedy: 2012
Very briefly, Taylor Swift dated Conor Kennedy, grandson of late President John F. Kennedy. The couple were semi-controversial – at the time, Kennedy was 18 and Swift 22.
While the romance was short-lived, it seemed to be a fast burn – Swift actually bought a house near the Kennedy’s in Hyannis Port, Massachusetts, while dating Conor Kennedy, and in August the Kennedy family infamously accused Swift of gate-crashing the wedding of Conor’s cousin Kyle. Swift denied the incident, but the relationship fizzled around that point.
‘Begin Again’ is widely considered to be about Kennedy, as it’s a song about starting to date after a particularly crushing heartbreak, with lyrics like “And you throw your head back laughing/Like a little kid/I think it’s strange that you think I’m funny ’cause/He never did.”
However, the track ‘That’s The Way I Loved You’, which is about dating a stable person but missing the tumultuous nature of a past love, could also hint at their break up, with lyrics like “He is sensible and so incredible/And all my single friends are jealous/He says everything I need to hear and it’s like/I couldn’t ask for anything better,” followed by a chorus with lyrics “I miss screaming and fighting and kissing in the rain/And it’s 2 AM and I’m cursing your name/You’re so in love that you act insane/And that’s the way I loved you.”
Harry Styles: 2012
Taylor Swift and Harry Styles as a couple could probably be counted as one of the most famous Hollywood romances of modern times, even though, like her relationship with Jake Gyllenhaal, it only lasted a few months.
The couple went public after paparazzi snapped them on a date at Central Park Zoo, and then the couple were photographed kissing on New Year’s Eve. But their romance crashed and burned, and by the 2012 Grammy Awards, Swift was singing ‘We Are Never Getting Back Together’ on stage in a British accent – with Styles in the crowd.
Harry Styles has inspired a myriad of Taylor Swift songs, if you believe fans. There is, most obviously, ‘Style’ – a song about a man with a “James Dean daydream look in his eyes” and an on-off love story. But fans believe most tracks off Swift’s album 1989 are about Styles, including ‘Out Of The Woods’, which featured a music video that saw Taylor Swift wearing Styles’ aeroplane necklace.
Calvin Harris: 2015
First spotted at a Wholefoods in March 2015, Taylor Swift and Calvin Harris initially seemed like a match made in music heaven. He was a famous UK DJ, she one of the biggest pop music stars in the world. Their relationship was completely public, including holiday snaps shared on her Instagram account and sightings across LA of the couple out on dinner dates.
Calvin Harris was the first boyfriend Taylor Swift took to an awards show, with the couple attending the Billboard Music Awards together and sharing a really cute kiss when Swift won Best Album, and the singer even danced in the crowd at Harris’ Coachella performance in 2016.
However, things took a sour turn by June that year, as per People. A source at the time said “There was no drama. Things just don’t work out sometimes, no one cheated.” However, Cosmopolitan theorised that Harris’ July song release ‘Ole’ might have been about Swift cheating. Sung from the perspective of a man having an affair with someone in a relationship, lyrics read ” “You’ve hidden my name in your phone so you can call me to tell me you’ve been going through hell/Left him alone and you booked in a hotel.”
Swift also alludes to potential cheating (or at least, leaving Harris for her next boyfriend, Tom Hiddleston) in the song ‘Getaway Car’. “I struck a match and blew your mind/But I didn’t mean it, and you didn’t see it,” the lyrics read, continuing “The ties were black, the lies were white/In shades of gray in candlelight/I wanted to leave him, I needed a reason.”
Tom Hiddleston: 2016
Speaking of, Tom Hiddleston is another of Taylor Swift’s boyfriends that is likely the centre of several popular Swift songs. The couple were first spotted together (kind of) at the 2016 Met Gala in May, which if you’ve been following this timeline, was right before her split from Calvin Harris was announced.
Whether they were just friends at the time or not, one month later The Sun published paparazzi photos of the couple kissing in Rhode Island. These came just weeks after her official split from Harris, and soon Hiddleston was in attendance at Taylor Swift’s famous Fourth Of July party, alongside plenty of famous friends.
Most notably, Tom Hiddleston was snapped in an ‘I heart T.S’ tank top, which he later told GQ was the result of falling over and needing a new top. “I wanted to protect the graze from the sun and said, ‘Does anyone have a T-shirt?’ And one of her friends said, ‘I’ve got this’ … And we all laughed about it. It was a joke.”
The couple split in September after just a few months of dating.
Joe Alwyn: 2017
Taylor Swift’s timeline with actor Joe Alwyn is a little confusing. In her track ‘Dress’, which fans believe is about her relationship with Alwyn, she sings “flashback to when you met me / Your buzz cut / And my hair bleached.” Alwyn was in attendance at the 2016 Met Gala, the same one where Swift met Hiddleston. But it wasn’t until a year later when their romance went public, with The Sun reporting the couple had been dating “for months”.
Whatever the case, Alwyn and Swift have now been together for six years – and their relationship is the most private of any in her past. Swift said in her 2020 documentary Miss Americana, “I was falling in love with someone who had a wonderfully normal, balanced life. We decided together we wanted our relationship to be private. I was happy. But I wasn’t happy in the way I was trained to be happy. It was happiness without anyone else’s input. We were just happy.”
After rumours flew that the couple had gotten engaged (based on lyrics in the track ‘Lover’), Alwyn told The Wall Street Journal “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.”
