Which Taylor Swift Ex Inspired the Best Songs? A Musical Ranking of Her Infamous Exes

There's no denying the lyrical genius of Taylor Swift. She's built a colossal career by spinning her romantic relationships into chart-topping songs. While not all of her music is autobiographical—she explained in an essay that her 2020 album Folklore was "a collection of songs and stories that flowed like a stream of consciousness"—many of her biggest hits are inspired by real-life love and heartache. Taking guesses at the muse behind each hit is half the fun.

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While Swift never confirms who her songs are about, Swifties have a theory for almost every single one. Even though they didn't end happily ever afters, let's take a look at which former flames seem to have left the biggest musical mark on her discography.

#15: Stephen Barker Liles

Potential Inspiration For:

• "Hey Stephen"

In 2008, Swift met (and quickly started crushing on) Stephen Barker Liles of the popular country duo Love and Theft when they opened for her during her Fearless Tour. According to Liles, they had a "real emotional relationship" and would talk on the phone quite a bit. While they never confirmed their romance, he told Taste of Country that he was flattered she wrote a song about him—especially a nice one—and actually wrote a song about her around the same time called "Try to Make it Anyway."

#14: Cory Monteith

Potential Inspiration For:

• "Mine"

Their brief love affair may have only lasted a month or so, but her chemistry with actor Cory Monteith was instant enough to supposedly inspire the heart-tugging single "Mine." Even though he publicly claimed that the two were just friends, a few snuggly paparazzi shots seemed to suggest otherwise. "The song is about what it would be like if I actually let my guard down," she told Rolling Stone while strategically not confirming the song's subject. Whatever label it was, it never went further than that. And sadly, Monteith passed away in 2013.

#13: Jordan Alford

Potential Inspiration For:

• "Picture to Burn"

One of Swift's first breakup bangers was the fiery "Picture to Burn," which she penned about a high school ex who cheated on her with one of her friends—ouch. The object of her musical wrath was Jordan Alford, whom Swift dated in her freshman year of high school. He went on to marry that friend, who told The Daily Mail: "We just thought it was funny. [Jordan] was like, ''I'm not a redneck! She makes me look like some redneck!''

#12: Taylor Lautner

Potential Inspiration For:

• "Back to December"

The second single off of her third album, Speak Now, was the apologetic "Back to December." Although she never named names, fans quickly speculated it was about Twilight actor Taylor Lautner. The two sparked a brief romance while filming Valentine's Day in 2009 and dated for a few months before splitting up later that year—in December. While she didn't admit to the subject, she did say that the lyrics reflect her genuine feelings of romantic regret. "Up until now, I haven't really felt like I really needed to apologize to someone," she admitted. "It's just necessary."

#11: Sam Armstrong

Potential Inspiration For:

• "Should've Said No"

This connection is a little murky as Swift has yet to confirm ever dating her supposed fellow classmate Sam Armstrong. But when the man took to Twitter to share photo evidence that suggested they not only dated but went to prom or some other formal together, Swifties quickly named him as the subject of her defiant single "Should've Said No." Seeing as how the song is all about her being cheated on, it's safe to say that her fans were not about to let him off the hook.

#10: Conor Kennedy

Potential Inspiration For:

• "Starlight"
• "Begin Again"

The summer of 2012 was a whirlwind for Swift, who was spotted ringing in the fourth of July with the Kennedy clan and their son, Conor Kennedy. While she had been a long-time friend and fan of the famous family—his grandmother,  Ethel Kennedy, even told reporters that they'd be "so lucky" if she became a Kennedy one day—their intense romance was no match for distance. They reportedly split after only a few months.

#9: Brandon Borello/Drew Dunlap

Potential Inspiration For:

• "Our Song"
• "Tim McGraw"
• "Fifteen"

The identity of the young man who inspired two of Swift's earliest singles is a bit convoluted. No one is confirming anything, but there's enough lyrical evidence for fans to narrow it down between Brandon Borello and Drew Dunlap. Whichever one it is, they supposedly dated when she was a freshman and he was a senior. And despite the obviously deep feelings she had, the romance didn't survive his move to college.

#8: Martin Johnson

Potential Inspiration For:

• "Love Story"
• "White Horse"
• "If This Was A Movie"

When Swift falls, she falls hard, as evidenced by her rumored brief fling with the frontman of Boys Like Girls, Martin Johnson. While it sounds like a made-up scenario for a cheesy rom-com, the pair actually met while writing a love song ("Two is Better Than One"). Sadly, their courtship didn't last as her team supposedly felt that Johnson wasn't the best romantic fit for her ever-rising public image.

#7: Calvin Harris

Potential Inspiration For:

• "I Forgot That You Existed"
• "Dancing With Our Hands Tied"
• "Bejeweled"
• "High Infidelity"
• "Look What You Made Me Do"

The relationship between Swift and Scottish DJ—and eventual ex—Calvin Harris had it all: lavish vacations, musical collabs, and a pretty public falling out. The pair dated for 15 months between 2015 and 2016, and while the breakup was initially reported as amicable, things quickly soured when she quickly moved on to actor Tom Hiddleston. Harris took to social media a few times to make some not-so-nice comments about her, which she later responded to with a nice collection of diss tracks. 

#6: John Mayer

Potential Inspiration For:

• "Dear John"
• "The Story of Us"
• "Superman"
• "Would've, Could've, Should've"

Swiftes, we've reached the John Mayer era. One of the most infamous relationships to date, Mayer and Swift had a brief but intense fling between 2009 and 2010—when she was 19, and he was 32. The romance may have never been confirmed, but it did result in a few scathing letters of sorts from Swift, the most famous of which is the track "Dear John." He shot back with his own snarky song titled "Paper Doll," which he later agreed sounded "a little pissed off."

#5: Jake Gyllenhaal

Potential Inspiration For:

• "All Too Well"
• 'We Are Never Ever Getting Back Together"
• "The Moment I Knew"
• "I Bet You Think About Me"
• "State of Grace"
• "The Last Time"
• "Maroon"

Swift and Jake Gyllenhaal had a short but electric romance from late 2010 to early 2011, with their brief relationship serving as the basis for arguably her best breakup track, "All Too Well." The 10-minute version released in 2012—along with the short film she wrote and directed in 2022—tells a pretty harrowing tale of heartache. The singer also takes some well-deserved jabs at their age difference, particularly with the line: "And I was never good at telling jokes / But the punchline goes / 'I'll get older, but your lovers stay my age.'"

#4 Tom Hiddleston

Potential Inspiration For

• "Getaway Car"
• "Cruel Summer"
• "I Did Something Bad"
• "Midnight Rain"
• "Gorgeous"
• "Long Story Short"

Following her split with Calvin Harris, Swift made waves with her whirlwind romance with actor Tom Hiddleston in 2016. The immediate flood of paparazzi-captured PDA had many people wondering if their relationship was just a publicity stunt, but Hiddleston confirmed numerous times that what they had was real. Rumor has it that they split because he "wanted the relationship to be more public than she was comfortable with." While it may not have been the love of her life, their time together did provide the singer with plenty of fodder for her music.

#3: Joe Jonas

Potential Inspiration For:

• "Forever and Always"
• "Better Than Revenge"
• "Holy Ground"
• "Last Kiss"
• "You All Over Me"
• "Mr. Perfectly Fine"

The two pop icons dated for a whopping three months while at the precipice of their respective music careers in 2008. But it all came crashing down when Jonas started developing feelings for actress Camilla Belle—and ended his relationship with Swift in a 27-second phone call.  This inspired a lot of her early tracks, many of which offered some not-so-subtle hints about the nature of their breakup. However, they seemed to have buried the hatchet after their brief feud, as evidenced by his now-wife Sophie Turner approving her 2021 release of "Mr. Perfectly Fine," which many fans believed to be about Jonas. Turner cheekily tweeted: "It's not NOT a bop."

#2: Harry Styles

Potential Inspiration For:

• "Style"
• "Out of the Woods"
• "Clean"
• "I Knew You Were Trouble"
• "All You Had to Do Was Stay"
• "I Wish You Would"
• "I Know Places"
• "Wonderland"
• "Question...?"

They may have only been together for a few weeks, but Harry Styles and Swift left an undeniable mark on each other. After being spotted together in December 2012, the pair dated throughout the holidays before splitting up while on vacation in the Virgin Islands. When she released her album 1989 two years later, many fans concluded that a lot of the tracks were about the former One Direction member. Swift even told Rolling Stone that "Style" should have been called "I'm Not Even Sorry."

#1 Joe Alwyn

Potential Inspiration For:

• "Dress"
• "...Ready For It?"
• "End Game"
• "Delicate"
• "Gorgeous"
• "King of My Heart"
• "Call It What You Want"
• "New Year's Day"
• "Lover"
• "London Boy"
• "Peace"
• "Invisible String"
• "Sweet Nothing"
• "Lavender Haze"
• "You're Losing Me"

Swift's longest-lasting romance to date was with British actor Joe Alwyn, whom she began dating in 2016. The couple kept an impressively low profile for the course of their six-year relationship, only being spotted out together a handful of times. Despite their desire for privacy, Swift never shied away from expressing her love for him through her music. Many of the songs on her albums Reputation and Lover allude to Alwyn, with many British easter eggs pointing to their connection.  Sadly, they recently split, and her new Midnights vault track "You're Losing Me" seems to tell us why.

"I'm the best thing at this party / And I wouldn't marry me either / A pathological people pleaser / Who only wanted you to see her."

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