Sparks flew between the two after collaborating on Mayer’s 2009 single “Half of My Heart.” However, their relationship sparked some controversy for their large age gap as Mayer was 32 and Swift was 19 at the time.
Their age difference is something Swift not-so-subtly called out in her 2010 breakup track “Dear John” off her album Speak Now, singing, “Dear John, I see it all now, it was wrong / Don’t you think 19’s too young to be played by your dark, twisted games when I loved you so? / I should’ve known.”
Swift previously attempted to play coy when asked about penning the track about Mayer. “How presumptuous!” she told Glamour in October 2012. “I never disclose who my songs are about.”
In 2019, the “Shake It Off” songstress announced she would be rerecording her first six albums — Speak Now included — after losing control of her masters to music manager Scooter Braun. Ahead of the July 2023 release of Speak Now (Taylor’s Version), Swift encouraged fans to spread kindness online instead of hate. “I’m not putting this album out so that you should go and feel the need to defend me on the Internet against someone you think I might have written the song about 14 million years ago,” she said during a June 2023 stop on The Eras Tour before performing “Dear John.”
The night before the rerecorded album’s release, Mayer added fuel to the rumor fire by sharing a cryptic message via Instagram. In a slideshow of pics, he posted a snap of the words “Please Be Kind” written in the sky at one of his concerts.
Keep scrolling for every song Swift has reportedly penned about her and Mayer’s relationship:
‘Dear John,’ Speak Now (2010)
“Dear John” is perhaps Swift’s most notable song about Mayer, from the tune’s title to its scathing lyrics about their 13-year-age gap to the pain she experienced following their 2010 split. Fans have even noted that the track’s soft guitar sound is similar to that of Mayer’s own music.
Released eight months after their February 2010 split, Swift sings, “And you’ll add my name to your long list of traitors who don’t understand / And I’ll look back and regret how I ignored when they said ‘run as fast as you can.’” Prior to his romance with Swift, Mayer was linked to Jennifer Love Hewitt, Jessica Simpson, Minka Kelly and Jennifer Aniston.
Mayer later said in a June 2012 interview with Rolling Stone that the song “humiliated him” and made him “feel terrible.” He continued: “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.”
The following year, he released the song “Paper Doll,” supposedly about his relationship with Swift. “And if those angel wings don’t fly, someone’s gonna paint you another sky,” he sings, seemingly referring to the “Dear John” lyrics “You paint me a blue sky and go back and turn it to rain.”
‘The Story of Us,’ Speak Now (2010)
Swift previously told USA Today that her muses for “The Story of Us” and “Dear John” were the same person. “’The Story of Us’ is about running into someone I had been in a relationship with at an awards show, and we were seated a few seats away from each other,” she explained. “I just wanted to say to him, ‘Is this killing you? Because it’s killing me.’ But I didn’t. Because I couldn’t. Because we both had these silent shields up.”
The song seemingly details the aftermath of their awkward encounter at the 2010 CMT Awards in June 2010. “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,” the lyrics state.
Swift goes on to compare their reunion to “a contest of who can act like they care less,” though she sings that she “liked it better when you were on my side.”
‘Ours,’ Speak Now (2010)
Unlike some of her other tracks seemingly about Mayer, “Ours” sheds a happier look on their relationship as it tells the story of a couple whose love persists despite other people’s objections. While the tune could be about Swift’s other romantic connections featured on Speak Now — such as Taylor Lautner or Joe Jonas — the song’s lyrics feature a description reminiscent of Mayer’s appearance.
“’Cause I love the gap between the teeth,” Swift sings in addition to mentioning the guy in the song has tattoos. Not only does Mayer have a gap between his two bottom front teeth but also a sleeve of tattoos on his left arm.
‘Superman,’ Speak Now (2010)
Much like “Ours,” lyrics from the Speak Now deluxe edition track “Superman” feature a description many believe could be Mayer. “Tall, dark and beautiful,” Swift sings in the song, seemingly describing the appearance of the tune’s titular superhero.
The lyrics also state, “He’s not all bad like his reputation.” The same year as Speak Now’s release, Mayer was heavily criticized after using the N-word and making misogynistic comments in interviews with Playboy and Rolling Stone.
‘I Knew You Were Trouble,’ Red (2012)
Swift continued to write about her past with Mayer on her fourth studio album, Red. While talking about the track “IKYWT” on Good Morning America, Swift described the song as about “kind of being frustrated with yourself because you have your heart broken and you knew when you first saw that person you saw all these red flags and you just went for it anyway.”
In the song’s chorus, she recalls that she knew someone — possibly Mayer — was trouble from early on in their relationship, and that she is ashamed for not recognizing it sooner.
‘Would’ve, Could’ve, Should’ve,’ Midnights (2022)
More than a decade after the release of “Speak Now” Swift dropped one of her most scathing songs about Mayer on her 10th studio album, Midnights. “And I damn sure would’ve never danced with the devil / 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,” she sings in the tune’s chorus, referring to the age she was during their romance. “Memories feel like weapons / And now that I know, I wish you left me wondering.”
Perhaps the song’s most gut-wrenching lyric comes in the bridge as Swift sings, “If clarity’s in death, then why won’t this die? / Years of tearing down our banners, you and I / Living for the thrill of hitting you where it hurts / Give me back my girlhood, it was mine first.”
Throughout the song, the Grammy winner also states that her fling with Mayer is something she regrets “all the time.”
‘Foolish One,’ Speak Now (Taylor’s Version) (2023)
Though “Foolish One” didn’t make the track list of the original Speak Now album, Swift released the track as one of many vault songs on the album’s July 2023 rerecording. Much like “Dear John,” Swift continues to recall how she missed the red flags in her and Mayer’s relationship. “And I’ll look back and regret how I ignored when they said / ‘Run as fast as you can,’” she sings.
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The lyrics also share insight into Swift’s emotions following their breakup and how she longed for reconciliation on Mayer’s part. “Foolish one / Stop checkin’ your mailbox for confessions of love / That ain’t never gonna come / You will take the long way, you will take the long way down,” she says in the song.
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