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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.

Jordan Alford was the muse behind Taylor Swift's Picture to Burn

Jordan Alford was the muse behind Taylor Swift's "Picture to Burn".

“Picture to Burn”

Muse: Jordan Alford

Lyric: "I hate that stupid old pick-up truck you never let me drive/You're a redneck heartbreak who's really bad at lying"

What Happened: Swift's first taste of expressing bitter heartbreak on a song came on the very first album. Before Joe or Harry, Swift's high school beau Jordan Alford hurt the young songwriter so deeply that she penned this searing, painful country track about how she'd tell all her friends that he was gay, date all of his friends and, of course, burn any photographic evidence of his existence. Swift's clapbacks have become more nuanced and progressive since then, but the track, released when she was a mere 16-years-old, offered an early glimpse at her pop power. 

In 2014, the source of Swift's bitterness was revealed: Alford cheated on her with his now-wife and a former friend of Swift's. Chelsea Alford dished the dirt to The Daily Mail and wondered if any other songs were about her and her husband. "We just thought it was funny," she recalled. "[Jordan] was like, 'I'm not a redneck! She makes me look like some redneck!' But other than that, we just thought it was kind of funny."

Drew Hardwick was the inspiration for Taylor Swift's "Teardrops on My Guitar"

Drew Hardwick was the inspiration for Taylor Swift's "Teardrops on My Guitar".

“Teardrops on My Guitar”

Muse: Drew Hardwick

Lyrics: "Drew looks at me, I fake a smile so he won't see/That I want and I'm needing everything that we should be/I'll bet she's beautiful, that girl he talks about/And she's got everything that I have to live without"

What Happened: Two important men in Taylor Swift's life get cited by name on her self-titled debut: Tim McGraw and Drew Hardwick. Swift technically dated neither of them, but her admiration from afar inspired two tender singles that helped her break onto the country charts. For "Teardrops," Swift reflects on being in love with a friend who loves someone else. "[He] would sit there every day talking to me about…another girl: how beautiful she was, how nice and smart and perfect she was," Swift revealed on her official site. "And I sat there and listened, never meaning it any of the times I said, 'Oh, I'm so happy for you.'"

Hardwick had no idea about the crush until the song came out, and he tried reaching out but Swift felt too awkward about it to return any of his phone calls. A few years later, Swift had a slightly more bitter tone about Hardwick, noting that he finally surprised her at her house a full two years after the song's debut. "I have theories about what he was doing," she told The Washington Post of Hardwick showing up on her driveway. "He had his friend with him, so maybe he was trying to prove to people that the song really is about him or whatever. Or maybe he was really trying to be friends. Or maybe he thought I was still pining away from him. Whatever!"

In late 2015, Hardwick and his wife Joni were arrested for child abuse.

Stephen Barker Liles was the inspiration for Taylor Swift

Stephen Barker Liles was the inspiration for Taylor Swift's "Hey Stephen".

“Hey Stephen”

Muse: Stephen Barker Liles

Lyrics: "Hey Stephen, I could give you 50 reasons/Why I should be the one you choose/All those other girls, well they're beautiful/But would they write a song for you?"

What Happened: Liles, a member of Love and Theft, was never technically Swift's boyfriend, but the pair mutually crushed on one another during Swift's 2008 tour, when his band were the opening act for the budding superstar. "I hadn't heard it yet, so she told me about the song," he told The Boot at the time. "But she didn't say, like, 'I wrote a nice song about you,' so I'm just thinking, 'What did I do?' [laughs] Because she doesn't really write very many nice songs about guys. So I was very relieved when it turned out to be a nice song, and it's actually one of the nicest things anybody's ever done for me." 

Joe Jonas was the inspiration for Taylor Swift

Joe Jonas was the inspiration for Taylor Swift's "Forever and Always".

“Forever and Always”

Muse: Joe Jonas

Lyrics: "Was I out of line?/Did I say something way too honest, made you run and hide/Like a scared little boy/I looked into your eyes/Thought I knew you for a minute, now I'm not so sure."

What Happened: Swift's relationship with Joe Jonas was a turning point in her celebrity and songwriting. Jonas was her first public, famous relationship and he also became the earliest tabloid-identified inspiration for her songs. The pair broke up just as she was wrapping up her 2008 album Fearless and ended up becoming a last-minute addition to her album, which was released in November of that year. 

In an interview with Rolling Stone, Swift described the relationship discussed on the song as one that was "really, really dramatic and crazy." She was scathingly honest with Ellen DeGeneres when discussing Jonas specifically, revealing to the talk show host that it was an "ouch." As opposed to her past relationships, dating a celebrity meant Swift had to see him everywhere, especially since the Jonas Brothers were at the height of their teen pop fame at the time. She even bluntly told the audience that he broke up with her "over the phone in 25 seconds."

Joe Jonas was the inspiration for Taylor Swift's "Better Than Revenge"

Joe Jonas was the inspiration for Taylor Swift's "Better Than Revenge".

“Better Than Revenge”

Muse: Joe Jonas

Lyrics: "She's not a saint and she's not what you think/She's an actress, whoa/She's better known for the things that she does/On the mattress, whoa/Soon she's gonna find/Stealing other people's toys on the playground/Won't make you many friends"

What Happened: Swift channels Paramore's bitter "Misery Business" on "Better Than Revenge," a scathing rip at ex Joe Jonas. Since the pair technically broke up in 2008, just as she was preparing the release of Fearless, much of her reflections on the end of their time together came out on 2010's Speak Now. On "Revenge," she takes aim at actress Camilla Belle, the girl Jonas hooked up with immediately after dumping Swift. Jonas and Belle met on the set of the Jonas Brothers' "Lovebug" video, which was filmed as his relationship with Swift was on the decline.

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

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

“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".

“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".

“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.