Ex-Factor: Taylor Swift's Best Songs About Former Boyfriends - Rolling Stone
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Ex-Factor: Taylor Swift’s Best Songs About Former Boyfriends

From “Dear John” to “Style,” here are the stories behind some of Taylor Swift’s most iconic break-up ballads and hits

Taylor Swift Sings Songs Ex-BF Jake Gyllenhaal Joe Jonas Harry Styles

Jake Gyllenhaal, Joe Jonas, John Mayer and Harry Styles were inspirations for Taylor Swift's songs

Lester Cohen/Getty, Kevork Djansezian/Getty, Jeff Kravitz/Getty

Like a new generation’s Carly Simon, Taylor Swift has played fun games with her fans in leaving clues and hints — both ambiguous and blunt — about the many male muses for her break-up songs. From high school crushes to Academy Award-nominated beaus, she’s apparently experienced the full spectrum of relationship joys and woes and has used her songs as a public diary to share her lessons and aches with her millions of fans. In an attempt to decode the lyrics and references, here are some of her best-known songs with clear inspirations for the subject matter.

Cory Monteith was the inspiration for Taylor Swift's "Mine"

Cory Monteith was the inspiration for Taylor Swift's "Mine".


Muse: Cory Monteith

Lyrics: "Do you remember, we were sitting there by the water?/You put your arm around me for the first time/You made a rebel of a careless man's careful daughter/You are the best thing that's ever been mine"

What Happened: Swift and Monteith — who had just gotten his break on the musical TV show Glee in 2010 — never publicly admitted to dating, and the pair were coy about their relationship and mutual affection for one another. In an interview with Yahoo! Music, she said that the inspiration for the song was inspired by seeing an "entire relationship flash" before her eyes after a prospective beau put his arms around her by the water. The pair both turned bright red when questioned in separate interviews about their relationship status while on Ellen and nothing more came of the pairing from then on. Monteith went on to date co-star Lea Michele until his tragic death in 2013 at age 31, but before he passed, the song was featured on Glee and sung by co-star Naya Rivera.

taylor swift john mayer

John Mayer was the inspiration for Taylor Swift's "Mine".

“Dear John”

Muse: John Mayer

Lyrics: "Dear John, I see it all now that you're gone/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"

What Happened: On "Dear John," Swift details a May-December romance gone awry. Mayer, 12 years Swift's senior, dated the singer-songwriter when she was 19 years old and later revealed that the song "humiliated" him. "It made me feel terrible," he told Rolling Stone in 2012. "Because I didn't deserve it. 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."

At the time of the song's release, Mayer had just gone on a hiatus following controversial, sexually explicit and semi-racist interviews with RS and Playboy. "I never got an email. I never got a phone call," he said. "I was really caught off-guard, and it really humiliated me at a time when I'd already been dressed down. I mean, how would you feel if, at the lowest you've ever been, someone kicked you even lower?" Later, he wrote the song "Paper Doll" about Swift.

taylor swift john mayer

John Mayer was the inspiration for Taylor Swift's "The Story of Us".

“The Story of Us”

Muse: John Mayer

Lyrics: "Now I'm standing alone in a crowded room/And we're not speaking and I'm dying to know/Is it killing you like it's killing me yeah"

What Happened: While "Dear John" was deep in the heartbreak of the demise of her relationship with John Mayer, "The Story of Us" detailed the aftermath. The Speak Now track follows her line of thinking during an awkward encounter with an ex-boyfriend, which turned out to be at the CMT Awards, where the two both performed earlier that year. The pair pretended to not see each other and continued to speak to others around them during the ceremony. "We both had these silent shields up," she told USA Today.

taylor swift taylor lautner

Taylor Lautner was the inspiration for Taylor Swift's "Back to December".

“Back to December”

Muse: Taylor Lautner

Lyrics: "I miss your tan skin, your sweet smile, so good to me, so right/And how you held me in your arms that September night"

What Happened: Taylors Swift and Lautner met on the set of Valentine's Day and, while not much else is known about their relationship, it's clear that Swift was the heartbreaker since "Back to December" is an apology. "Sometimes you learn a lesson too late and at that point you need to apologize because you were careless," she told MTV News. 

taylor swift jake gyllenhaal

Jake Gyllenhaal was the inspiration for Taylor Swift's "We Are Never Ever Getting Back Together".

“We Are Never Ever Getting Back Together”

Muse: Jake Gyllenhaal

Lyrics: "I'm really gonna miss you picking fights/And me falling for it, screaming that I'm right/And you would hide away and find your peace of mind/With some indie record that's much cooler than mine"

What Happened: Even though Gyllenhaal was clearly the source of an intense heartbreak for Swift, he's worth thanking for inspiring the former country star's full transition to pop princess. Red ended up being a huge musical jump for Swift and the playful "We Are Never Ever Getting Back Together" is responsible for launching that. The couple dated in late 2010, having been spotted all over Brooklyn together. In the music video, she committed to revealing his inspiration for the single by hiring a look-a-like actor as her love interest and referencing the scarf he reportedly gave her as a present – which plays a pivotal role in the song "All Too Well."

Fueling even more speculation, Swift takes a dig at Gyllenhaal's love for indie music. The actor had dated indie darling and Rilo Kiley singer Jenny Lewis prior to Swift, and after he and Swift broke up, the actor brought Lewis to the Golden Globes as his date.

taylor swift jake gyllenhaal

Jake Gyllenhaal was the inspiration for Taylor Swift's "All Too Well".

“All Too Well”

Muse: Jake Gyllenhaal

Lyrics: "Time won't fly, it's like I'm paralyzed by it/I'd like to be my old self again, but I'm still trying to find it/After plaid shirt days and nights when you made me your own/Now you mail back my things, and I walk home alone"

What Happened: "All Too Well" is a masterpiece of the break-up ballad form as Swift details the intimacy of a relationship that falls apart and the pain of having to piece one's self back together again afterwards. For the track, she reunited with Liz Rose, a songwriter Swift penned many of her earliest hits with. The track talks about a trip to upstate New York in the autumn, a location and time of year she and Gyllenhaal were heavily photographed experiencing together. She even gives a shout out to his sister and actress Maggie Gyllenhaal, who apparently still has the scarf Jake gave Swift for her birthday that December.

"'All Too Well' was the hardest to write because it took me a long time to filter through everything I wanted to say," Swift said about the painstaking process of writing the story of their short-lived but seemingly passionate love affair. "It started out being a 10-minute song, which you can't put on an album. I had to filter it down to a story that could work in the form of a song."

taylor swift joe jonas

Joe Jonas was the inspiration for Taylor Swift's "Holy Ground".

“Holy Ground”

Muse: Joe Jonas

Lyrics: "Tonight I'm gonna dance for all that we've been through/But I don't wanna dance if I'm not dancing with you/Tonight I'm gonna dance like you were in this room/But I don't wanna dance if I'm not dancing with you"

What Happened: Even four years later, Jonas remained a huge inspiration for Swift's songs. On "Holy Ground," Swift is more positive in her reflection of what went down between the pair. Rumors of the song being about Jonas were fueled by his appearance at a pair of her concerts in 2011, showing a rekindled friendship between the former couple who had grown up and moved on.

taylor swift conor kennedy

Conor Kennedy was the inspiration for Taylor Swift's "Starlight".


Muse: Conor Kennedy

Lyrics: "I met Bobby on the boardwalk, summer of '45/Picked me up late one night at the window/We were 17 and crazy, running wild, wild"

What Happened: For most of 2012, Swift dated Conor Kennedy, who was 18 years old at the time. The relationship was so intense that Swift bought a home next door to the Kennedy family's Massachusetts compound. While Swift has never confirmed any particular songs about Kennedy specifically, she did seem to glean inspiration from his grandmother Ethel and Ethel's relationship with Robert F. Kennedy, who was assassinated in 1968. "Starlight" reflects on Ethel and Bobby's early romance, dancing during the summer of 1945 with one another. Ethel Kennedy loved Swift as much as the singer loved her — the matriarch called the then-22-year-old "spectacular."

taylor swift harry styles

Harry Styles was the inspiration for Taylor Swift's "Style".


Muse: Harry Styles

Lyrics: "'Cause you got that James Dean daydream look in your eye/And I got that red lip classic thing that you like/And when we go crashing down, we come back every time/'Cause we never go out of style/We never go out of style"

What Happened: Swift's relationship with the One Direction heartthrob Harry Styles was extremely short-lived. The pair barely lasted a month but traveled the world together in that time. On "Style," she keeps it simple, referencing his wayward, flirtatious ways – especially since Styles is best-known for the number of girlfriends he's had since joining the boy band. "We should have just called it 'I'm Not Even Sorry,'" she joked in an interview with Rolling Stone in August of 2014. 

Much of the lyrics on 1989 are more ambiguous than the songs of her past, and she heavily hinted in her RS cover story that Styles had been a huge inspiration for many of the songs. Still, "Style" refers back to her years of bluntly naming names in her song titles and lyrics.

taylor swift harry styles

Harry Styles was the inspiration for Taylor Swift's "Out of the Woods".

“Out of the Woods”

Muse: Harry Styles

Lyrics: "Looking at it now, last December/We were built to fall apart, then fall back together/Your necklace hanging from my neck/The night we couldn't quite forget/When we decided (We decided)/To move the furniture so we could dance/Baby, like we stood a chance/Two paper airplanes flying, flying, flying"

What Happened: Swift and Styles were first spotted together in December 2012, and they parted ways that following January. Before they were photographed together, Swift had been sporting Styles' paper airplane necklace out in public, which turns into a metaphor for the short flight of their relationship. Also referenced on the song is a snowmobile accident the pair experienced that winter. Around Christmas of 2012, Styles had a chin injury from the accident though little was known about their joint experience at the time. She detailed the experience more in her Rolling Stone cover story, stating that all she had to do to keep anyone from leaking the information to the press was look them in the eyes and ask for discretion with their privacy.

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