A definitive timeline of Taylor Swift's famous exes — and the songs she's written about them
Cryptic lyrics, easter egg hunts and catchy pop melodies can only mean one thing: we have a new Taylor Swift album.
The award-winning musician announced the release of her new album — The Tortured Poets Department — at the Grammys back in February, sparking her loyal fans to brace themselves for her hallmark lyrical clues, hidden messages, and a musical nod to her famous exes. Read our review of the new Taylor Swift album here.
Arielle Steele, a dedicated Swiftie who writes a monthly newsletter called Swiftian Theory along with friends Natasha, Kate and Satu, says: “I’m genuinely a bit scared by what it will do to me.” “I’ll be looking for clues and easter eggs (as Taylor calls them) that connect the dots between this album and some of her earlier music.”
Telling deep and meaningful stories through her lyrics is something that Swift does expertly. Listeners come for the catchy beats and fun melodies, but stay for the intricate storytelling and sophisticated themes which run between songs and albums. “These songs reflect back on our own lives. They become just as much about us as they are about her,” says Steele. “I’m planning to set aside the morning on Friday to listen to the new album on my own, before frantically messaging my Swiftie group chat for deep lyric analysis.”
It’s no wonder Swift is so successful, with 14 Grammy wins to her name — four of which are for Album of the Year (a record that no other artist in history has managed, by the way). She’s sold over 56 million albums, and made it onto the iconic Forbes Rich List by achieving billionaire status in October 2023.
Swift has dated some of the most famous men in Hollywood and is known for pouring her heart into her songs, with fans piecing together clues and lyrical hints to decipher who the songs are about. Her new album is about actor ex Joe Alwyn, who Swift was with for six years before their split in 2023, and Matty Healy, the wild 1975 frontman she dated briefly last year.
Ahead of the release of the new album, let’s take a trip down memory lane (Taylor’s Version) for a reminder of her long list of ex lovers (as she puts it herself).
Ex: Joe Jonas
When they dated: 2008
Songs about him: Forever & Always (Fearless), Mr Perfectly Fine (Fearless), Last Kiss (Speak Now), Holy Ground (Red)
Key lyrics: “Hello, Mr Perfectly fine / How's your heart after breakin' mine?”
Who he’s with now: Stormi Bree
Swift dated fellow musician Joe Jonas for three months in the summer of 2008, after joining the Jonas Brothers on tour. It was a pretty sour breakup, with Jonas reportedly dumping Swift over the phone before getting together with actress Camilla Belle.
How much can you have to say about a relationship after only three months? Apparently, a lot. Swift wrote several songs about Jonas, many of which have cutting lyrics, like the lines: "Oh, he's so smug, Mr. 'Always wins' / So far above me in every sense" from Mr Perfectly Fine.
She may not be on good terms with Jonas, but Swift is great friends with his now ex-wife Sophie Turner. Swift even loaned Turner her NYC apartment during the divorce. You can’t say she’s not a girl’s girl.
Ex: Taylor Lautner
When they dated: 2009
Songs about him: Back to December (Speak Now)
Key lyrics: “So, this is me swallowing my pride / Standin' in front of you sayin', "I'm sorry for that night"”
Who he’s with now: Taylor Dome
Swift’s split from actor Taylor Lautner was a lot more amicable. After meeting on the set of the film Valentine’s Day in which they both starred, the pair dated for a few months in 2009. It seems that Lautner was more into the relationship than Swift was, and her song about him Back to December serves as an apology for letting him go. The pair have stayed friends, and Lautner — who it would seem exclusively dates people called Taylor and married nurse Taylor Dome in 2022 — appeared in the music video for I Can See You in 2023.
Ex: John Mayer
When they dated: 2009-2010
Songs about him: Dear John (Speak Now), The Story of Us (Speak Now), Superman (Speak Now), Would’ve, Could’ve, Should’ve (Midnights)
Key lyrics: “All the girls that you've run dry have tired lifeless eyes / 'Cause you burned them out”
Who he’s with now: Currently unknown
The pair dated briefly after Swift featured on Mayer’s song Half of My Heart. Although the pair were only linked for a short time, there are many songs rumoured to be about him. The relationship was toxic and the split was bitter, but there’s no report on the exact reason they parted ways. Swift’s song Dear John is undoubtedly about the fellow musician, and recounts their volatile relationship. The lines “Don't you think I was too young to be messed with? / The girl in the dress, cried the whole way home” highlights the controversial age gap — Swift was 19 when she dated 32-year-old Mayer.
The song Would’ve, Could’ve, Should’ve, which appears on the later album Midnights, reveals Swift’s reflection on their time together and the impact it had on her, with the lyrics: “At 19, and the God’s honest truth is that the pain was heaven / And now that I’m grown, I’m scared of ghosts."
Ex: Jake Gyllenhaal
When they dated: 2010-2011
Songs about him: We Are Never Ever Getting Back Together (Red), I Almost Do (Red), State of Grace (Red), All Too Well (Red) and its 10 minute version, The Moment I Knew (Red)
Key lyrics: “I'll get older, but your lovers stay my age”
Who he’s with now: Jeanne Cadieu
Much of Swift’s fourth studio album, Red, is about her whirlwind relationship with actor Jake Gyllenhaal — which only lasted three months. It was a lesson in love-bombing, with the actor reportedly flying Swift to London on a private jet for a date, but then breaking up with her over text a couple of months later (ouch). One of the sorest points of the relationship was when Gyllenhaal didn’t show up to Swift’s 21st birthday — he was 29 at the time. The song The Moment I Knew is all about her heartbreak and embarrassment, opening with the line: “You should’ve been there”.
Ex: Harry Styles
When they dated: 2012-2013
Songs about him: Out of the Woods (1989 Deluxe), I Know Places (1989 Deluxe), Clean (1989 Deluxe), Style (1989 Deluxe), Is It Over Now? (1989 Taylor’s Version), Question…? (Midnights)
Key lyrics: “You got that James Dean daydream look in your eye”
Who he’s with now: Taylor Russell
Ah, 2012. Twilight was killing it at the box office, Tumblr was in its heyday, and Taylor Swift and Harry Styles were music’s biggest power couple. They had a fairly short relationship after meeting at the Kids’ Choice Awards, and have remained friends since their amicable split.
Many songs from Swift’s album 1989 — both the deluxe version and the re-released Taylor’s Version — are about the One Direction alum. In contrast to the excruciating heartbreak following her split from Jake Gyllenhaal, the songs about Harry Styles are much more upbeat, with nods to his charming appearance and the positives of their time together.
Ex: Calvin Harris
When they dated: 2015
Songs about him: Getaway Car (Reputation), Bejeweled (Midnights), High Infidelity (Midnights)
Key lyrics: “You know there's many different ways that you can kill the one you love / The slowest way is never loving them enough”
Who he’s with now: Vick Hope
Fast forward a few years and Swift decided to stick with the British theme, dating Scottish DJ and producer Calvin Harris. They were introduced by none other than Ellie Goulding in a move that was motivated by — get this — height. “They're both really awesome and both really tall, they'll be brilliant together,” Goulding told the media at the time.
The couple were together for 15 months (Swift’s longest public relationship at the time) but suffered a messy breakup in the public eye. The point of contention? Their collaborative hit song This Is What You Came For. After the media reported that Swift wrote the song, Harris went on a Twitter tirade, which he later said he regrets. “I'm not good at being a celebrity. But when it ended, all hell broke loose,” he told GQ.
Dating tall people obviously worked for Harris, who is now married to Radio 1 presenter Vick Hope. She recently revealed on her radio show that she bops along to Swift’s music when Harris is out of the house. There are definitely worse things to hide from your husband.
Ex: Tom Hiddleston
When they dated: 2016
Songs about him: Getaway Car (Reputation)
Key lyrics: “I wanted to leave him, I needed a reason”
Who he’s with now: Zawe Ashton
After the chaotic fallout of her relationship with Calvin Harris, Swift surprised everyone by dating British actor Tom Hiddleston shortly after. They met at the 2016 Met Gala and although it was only a three-month affair, by all accounts it was a positive time for them both. “Taylor is an amazing woman. She's generous and kind and lovely, and we had the best time,” Hiddleston told GQ in 2017.
Hiddleston didn’t have lots of songs written about him like other exes, but fans believe the song Getaway Car references how hastily they got together and that the ex she was “running away” from was Calvin Harris. The lyrics: “The ties were black, the lies were white” supposedly reference the black tie Met Gala where they met.
Ex: Joe Alwyn
When they dated: 2017-2023
Songs about him: The majority of the Lover and Reputation albums (at least the stuff that isn’t about Kimye), and now So Long, London (The Tortured Poets Department)
Key lyrics: "You know I love a London boy"
Who he’s with now: Unknown
Oh, poor Joe. This English actor has been through the wars a bit with Taylor’s fans, having been the subject of much of her recent material — and he would be, given that their relationship spanned a pretty substantial six years.
Plus, Alwyn is notoriously private (a trait that Swifties have not always enjoyed), so most of the insight into the pair’s relationship came from Taylor’s songs. She started with the effusive love songs on Lover (he literally is Lover, and he’s the subject matter of Cruel Summer too) and then moved onto more established relationship material on Reputation (in New Year’s Day, she sings "I want your midnights / But I'll be cleaning up bottles with you on New Year's Day”). Cut to: Midnights, which fans have ostensibly branded a break up album.
The claws were out for Alwyn ahead of The Tortured Poets Department’s release, with many protective fans expecting to reconcile with the worst of Swift and Alwyn’s relationship. But as it turns out, he’s not even the main focus. Her main tribute to him is So Long, London, but otherwise, it’s seemingly all about...
Ex: Matty Healy
When they dated: 2023-2023
Songs about him: The majority of The Tortured Poets Department
Key lyrics: “You smoked, and then ate seven bars of chocolate. We declared Charlie Puth should be a bigger artist. I scratch your head, you fall asleep, like a tattooed Golden Retriever”
Who he’s with now: Gabbriette Bechtel
What a snatch and grab! Just when we thought Joe Alwyn was about to be sacrificed, the album turns out to be all about The 1975’s controversial front man. Healy divided Swifties during the period he dated Taylor, with many feeling disappointed that she had chosen to date someone with such a history of offensive comments (including towards Ice Spice, one of her recent collaborators).
Nonetheless, the period clearly left its mark on her, with much of the album centred around Healy’s bad boy persona and the pair’s brief love affair. RIP Joe, you had your time, and now you’re safe from the Swifties. One can only imagine what’s in store for Travis Kelce.
