Pop star Taylor Swift has made a name for herself through her intensely personal songs, many of which are about her high-profile romantic relationships. Though Swift has come under fire for her song content, she’s dismissed the critics and continues to do what she does best. These songs are known to be about the men in her life, from her teens up to the present day.
1. All Too Well
All Too Well may have become Taylor Swift’s most famous song about an ex—but a decade after its initial release. With the release of All Too Well (Taylor’s Version) in 2021, it became clear to fans that the song was written about actor Jake Gyllenhaal, whom Swift dated briefly in 2010.
At the time, she was only 21, and he was 30, and the age difference played a role in their breakup. With the rerelease of the song, fans flooded Gyllenhaal’s social media pages with opinions and demands for him to return Swift’s red scarf, which was mentioned in the song.
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2. We Are Never Ever Getting Back Together
Swift’s snarky breakup anthem We Are Never Ever Getting Back Together topped the charts in 2012. One of the most memorable lines of the song features Swift saying in a tone dripping with sarcasm: “You hide away and find your peace of mind with some indie record that’s much cooler than mine.” Fans have deduced that the song is about Jake Gyllenhaal; Swift’s other songs about him have mentioned his preference for indie music and her feeling that he looked down on her career.
Swift’s 2014 song Style was one of the most popular songs of the year, describing two people who can’t stay away from one another because they’re simply a classic pairing. The title might be a little on the nose, as it is thought to be about Harry Styles (get it?), who Swift dated briefly between 2012 and 2013.
Not only does the timeline fit the song’s release, but sharp-eyed fans also noted the reference to extreme secrecy; paparazzi dogged Swift and Styles during their relationship, which forced them to go to extreme lengths to find privacy.
4. Back to December
Back to December is a slow ballad featured on the 2010 album Speak Now. The song is widely thought to be a reference to Swift’s time dating Taylor Lautner, whom she met on the set of Valentine’s Day.
They only dated briefly, and signs point to Swift being the one to break things off. While many of her songs deal with the heartbreak of rejection, Back to December is a heartfelt apology to someone she feels she mistreated. It seems to hold a reference to him consoling her after she was humiliated by Kanye West during the 2009 VMAs.
5. Holy Ground
It’s not entirely clear who Holy Ground was written for, but some fans think it might be an ode to Joe Jonas. This would seem odd, considering that the pair had broken up in 2008, and Holy Ground wasn’t released until 2012.
However, this could make sense, considering that they were photographed together in 2011, leading to rumors that they had started their relationship once again. Though the rumors never panned out, what did seem true was that the two of them had forgiven each other and moved on, sparking a friendship in the ruins of their relationship.
6. Dear John
It’s not unknown for Swift to namecheck her exes in songs. In Dear John, she uses a play on words (a Dear John letter is slang for a breakup letter written to a deployed soldier) to address her ex-boyfriend John Mayer.
Swift and Mayer dated for several months between 2009 and 2010 after collaborating on the song Half of My Heart. At the time, she was 19, and he was 32. Mayer was also one of the few exes to comment on the song she wrote for him, saying that he thought it was a low blow from the former country star.
Mine is one of Swift’s singles that has largely been overshadowed by many of her bigger hits. Released on her 2010 album Speak Now, the song was reportedly about late actor Cory Monteith. Swift and Monteith only dated for a few weeks in 2010 before calling it off (as it seems, a decision made by Swift), and the song described a relationship with a man that she didn’t yet know.
Mine was later performed on Glee, the show in which Monteith starred. After the actor’s death in 2013, Swift expressed shock and grief on Twitter.
8. Picture to Burn
Writing about her ex-boyfriends has been a fixture of Taylor Swift’s songwriting career since the very beginning. One of her earliest hits was Picture to Burn, a countrified diss track about a “redneck heartbreak.”
It was written about her high school boyfriend, Jordan Alford, who cheated on her with her friend. Reportedly, Alford is now married to the woman he left Swift for; his wife gave an interview expressing amusement over the song’s depiction of Alford as a “country hick” who was overly possessive of his pickup truck, saying that the image wasn’t accurate.
9. Forever & Always
Forever & Always was a scathing breakup song that didn’t pull any punches on Swift’s album Fearless. It was written about Joe Jonas, whose three-month relationship with the country singer ended with a brief phone call.
Notably, Jonas was Swift’s first high-profile boyfriend since her big break, which meant they were in the public eye both during and after their relationship. Forever & Always includes some brutal put-downs, particularly the line “Did I say something way too honest/Made you run and hide like a scared little boy.” Years later, Swift said she regretted bashing him so hard in public, blaming it on “teenage drama.”
10. Out of The Woods
Swift’s 2014 hit Out of The Woods is one of many songs rumored to be about her time dating singer Harry Styles. Swift never confirmed the rumors but stated that it was about the point in a relationship where each party wonders if they’ve finally reached the point of safety instead of wondering if everything is about to fall apart.
Fans noted the song’s reference to paper airplanes, which seemed to be a nod to Styles’ and Swift’s matching paper airplane necklaces. It also famously mentions “20 stitches in the hospital room,” a reference to a snowmobiling incident that resulted in Styles getting 20 stitches on his chin.
11. I Knew You Were Trouble
It isn’t officially known who Swift was singing about when she wrote I Knew You Were Trouble. But the timing of the song’s release points to a couple of different possibilities.
Most fans seem to think that the song is about Harry Styles. However, Jake Gyllenhaal has also been suggested. Either of these exes would work based on the timeline of their relationships and the release of Swift’s album Red. The singer herself has never confirmed who the song is about, so it comes down to fan conjecture.
12. Last Kiss
Last Kiss is a mournful ballad that Swift released on her 2010 album Speak Now. Though she has never confirmed who it was about, fans widely consider the song to be about Joe Jonas.
Swift and Jonas dated for a few short months in 2008, when she was just 18 years old. She did confirm that she had written a song about him for that album. Even more shocking was her public confession that he broke up with her on a phone call that lasted under 30 seconds.
13. Better Than Revenge
Better Than Revenge can take its place as one of Swift’s most vicious breakup songs of all time. In it, she levels her sights not just on her ex-boyfriend but on his new woman. Many fans think that the song was written about Joe Jonas, who had a rebound relationship with actress Camilla Belle just after he and Swift called it quits. Reportedly, Jonas and Belle met while shooting a music video while he was still dating Swift, making the lines about her “stealing other people’s toys” make sense.
14. Our Song
Our Song was the track that launched Taylor Swift’s career back in the mid-2000s when she was still solidly a country star and only in her teens. Like several of Swift’s other early hits, it was inspired by her relationship with her high school boyfriend, Brandon Bordello. She first performed it at her high school talent show.
When she released her first album in 2006, Our Song became a massive hit and paved the way for her to become a superstar. Though Bordello and Swift broke up when he went to college, they remained on good terms.
15. The Story of Us
After Swift’s high-profile breakup with singer John Mayer, the public got a full view of the aftermath: her release of Dear John and his responding interview, in which he dressed her down for humiliating him.
Later that year, the two of them were spotted at the CMT Awards (they were both scheduled to perform). Both fans and the press noted that the singers pointedly ignored each other—an experience that Swift later detailed in her song The Story of Us. Mayer and Swift’s relationship ended on a particularly bitter note, with Mayer later releasing the song Paper Doll about his ex-girlfriend.
16. Getaway Car
You might not remember that Swift briefly dated actor Tom Hiddleston in 2016. Getaway Car was written about their relationship, which for Swift was a rebound after breaking up with Calvin Harris.
The song compares the rebound to a getaway car providing an escape from loneliness and heartbreak. But from the opening line: “Nothing good starts in a getaway car.” Swift makes it clear that the relationship is doomed to fail. She eventually turns on the man in the song and takes her own getaway car, this time fleeing from him.
17. The Last Time
The Last Time was a 2012 duet with Gary Lightbody, released on her album Red. Many of the songs on the album were inspired by Swift’s relationship with Jake Gyllenhaal, and fans seem to think that “The Last Time” is another nod to the actor. When Gyllenhaal and Swift began dating, rumors were flying that he was connected to actresses Anna Kendrick and Rachel Bilson as well. This seems to be related to the lyrics where Swift describes being compared to other women.
Ours is another one of Swift’s lesser-known songs, having been featured on the deluxe version of her 2010 album Speak Now. The song is widely considered to be about John Mayer; their relationship was the subject of intense media criticism because of their 13-year age difference (she was 19, and he was 32).
Other, more explicit references to Mayer’s physical characteristics include a gap between his teeth and tattoos. Ours is a lightheartedly defiant song pushing back against the critics; Swift later references this in Dear John when she says she wishes she had listened to the warnings.
19. Hey Stephen
Hey Stephen is a poppy, upbeat song that was included in Swift’s 2008 album Fearless. The song was written for Stephen Barker Liles, a member of the band Love and Theft. They toured with Swift in 2008 as her opener, and though Swift and Liles never dated, they did enjoy some mutual flirtation.
Things ended without bitterness, though Liles later joked that he was nervous when she told him she had written a song about him. Liles is now married with two children.
20. I Know Places
I Know Places was released on Taylor Swift’s 2014 album 1989. The song follows a couple trying to find privacy as they evade the paparazzi. Because of this, it is widely assumed to be about Swift’s relationship with One Direction star Harry Styles.
During their time dating, the couple was relentlessly dogged by the media and found it difficult to enjoy time alone. Swift’s songs about Styles include frequent references to hiding, sneaking around, and feeling hunted. In I Know Places, she compares it to a foxhunt and describes her fears that the spotlight will spoil their fragile relationship.
21. I Bet You Think About Me
Swift wrote I Bet You Think About Me in 2011, intending for it to be released on her upcoming album Red. However, the track was shelved until a decade later, when she rereleased the album as Red (Taylor’s Version).
Fans quickly deduced that it was a song about Jake Gyllenhaal, not just because of the time of its composition, but also because it describes an ex as someone with elevated tastes. Feelings of inadequacy are a frequent theme in Swift’s songs about Gyllenhaal.
22. Begin Again
Many people forget that Taylor Swift’s list of famous exes includes Conor Kennedy, the son of Robert F. Kennedy. They dated for several months in 2012 when Swift was 22 and Kennedy was 18. Though it has never been confirmed, many fans seem to think that her 2012 song Begin Again is a nod to their relationship.
The song is essentially about the hope at the start of a relationship and how easily it can be dashed. Swift and Kennedy broke up after finding it too challenging to navigate long-distance.
23. I Almost Do
I Almost Do was released on 2012’s Red, an album that Jake Gyllenhaal heavily inspired. In typical Swift fashion, it included a hidden message, which fans decoded to “wrote this instead of calling.” This is in line with the song’s theme: being tempted to rekindle a relationship when you know it’s a bad idea.
Swift and Gyllenhaal seemed to have several opportunities to reconnect but realized that they weren’t a good fit, and it was just a recipe for more heartbreak.
24. Tim McGraw
Tim McGraw was one of Swift’s earliest hits, marking her breakthrough into the Billboard Hot 100. Swift composed it when she was a freshman in high school and dated a senior, Brandon Bordello. Their relationship ended when Bordello graduated high school and moved away for college.
The song shows that Swift’s career began with writing about her personal life from the very beginning. She later said that Bordello bought her debut album and reached out to her to say that he thought it was fantastic. The two of them parted on good terms.
Swift said that Clean was inspired by her walking around London and suddenly realizing that her ex-boyfriend was in the same city. She realized she had finally moved past their relationship when her reaction was simply to wish him well rather than feeling pain or anger over their breakup. Because of the reference to London, fans consider the song a clear reference to Harry Styles, though Swift has never elaborated beyond that. Though many of her songs describe heartbreak after the end of their relationship, Clean shows she has healed and moved on.
26. Should’ve Said No
Should’ve Said No was released on Taylor Swift’s debut album in 2006. It was a pointed breakup anthem to her high school boyfriend, Sam Armstrong. Armstrong cheated on her, inspiring a flurry of creativity that let Swift compose the song in just five minutes. Should’ve Said No lists all of the excuses that her ex gave her after she found out about what he’d done. Ultimately, she flatly refuses them all, making it clear that, in her mind, there is no coming back from this.
27. Would’ve, Could’ve, Should’ve
Would’ve, Could’ve, Should’ve is another song widely rumored to be about John Mayer, though this has never been confirmed. Though it came out more than a decade after their relationship ended, the song reflects a romance of Swift’s youth. She describes how the years have given her more insight into the problems of the relationship, including the power differential between them and the breaking of her teenage innocence (Mayer is 13 years older than her). The song also details the lasting trauma of the connection and how much she regrets it now.
28. The Moment I Knew
Swift’s relationship with Gyllenhaal famously began to deteriorate when he failed to attend her 21st birthday party—an event mentioned in several songs. This is reiterated in The Moment I Knew, a song released on the deluxe version of Red.
The song ends with Gyllenhaal calling her to apologize; Swift’s response is also an apology for putting her heart on the line. Though their breakup wasn’t officially announced until the following month, it seems clear that this failure was the nail in the coffin for their relationship.
29. State of Grace
State of Grace was first released on 2012’s Red before undergoing a rerelease when Swift put out Red (Taylor’s Version) nearly a decade later. The song seems to have been inspired by her time dating Jake Gyllenhaal, who inspired many of the songs on Red.
The most overt hint that Gyllenhaal is the subject is in the line “Twin fire signs, four blue eyes.” Fans were quick to note that both Gyllenhaal and Swift have birthdays in December, making them each a Sagittarius (the star sign denoted by fire). They also both have blue eyes.
Things seem to have been looking up for Taylor Swift in her personal life since she began dating Joe Alwyn in 2016. They met at the Met Gala in May of that year, a meeting which Swift seems to reference in her song Dress. The track mentions their distinctive hairstyles during their meeting; at the 2017 Met Gala, Swift notably departed from her signature look and sported a bleached blonde bob. Meanwhile, Alwyn had a buzz cut, described in Dress.
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