Unveiling Taylor Swift's Unfiltered Emotions: The Ultimate Guide to Her Ex John Mayer-Inspired Songs

Taylor Swift and John Mayer Shutterstock; Matt Baron/BEI/Shutterstock

Taylor Swift has found no greater muse than relationships, as evidenced by her numerous songs that appear to chronicle her intense love affair with John Mayer. The sparks ignited between them following their collaboration on Mayer's hit single, "Half of My Heart," released in 2009. However, their relationship faced scrutiny due to the considerable age difference, with Mayer being 32 and Swift only 19 at the time.

In her 2010 breakup track "Dear John" from the album Speak Now, Swift openly addressed the age difference between them, singing, "Dear John, I now understand, it was a mistake / Don't you think 19 is too young to be manipulated by your deceptive tactics, despite my love for you? / I should have been aware."

When questioned about writing the song about Mayer, Swift tried to be evasive. "How presumptuous!" she exclaimed to Glamour in October 2012. "I never reveal the inspiration behind my songs."

In 2019, the singer of the song "Shake It Off" announced her plan to re-record her first six albums, including Speak Now, due to losing control of her original recordings to music manager Scooter Braun. Prior to the anticipated release of Speak Now (Taylor's Version) in July 2023, Swift urged her fans to promote kindness online instead of engaging in hate. During a tour stop in June 2023, she stated, "I am not releasing this album for you to defend me against someone you believe I wrote a song about 14 million years ago." Swift made these remarks before performing the song "Dear John."

Just before the re-recorded album was released, Mayer added to the speculation by sharing a mysterious message on Instagram. He uploaded a slideshow of pictures which included a photo of the words "Please Be Kind" written in the sky during one of his concerts.

Keep scrolling for every song Swift has reportedly penned about her and Mayer’s relationship:

‘Dear John,’ Speak Now (2010)

Swift's song "Dear John" is widely recognized as a significant reflection on her relationship with Mayer. The title itself, along with the piercing lyrics addressing their 13-year age difference and the anguish she endured after their breakup in 2010, emphasize the emotional depth of the song. Fans have also noticed similarities between the soft guitar sound in "Dear John" and Mayer's own musical style.

Following their separation in February 2010, Swift released the song eight months later. In the lyrics, she laments, "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 involvement with Swift, Mayer had been romantically linked to Jennifer Love Hewitt, Jessica Simpson, Minka Kelly, and Jennifer Aniston.

In a June 2012 interview with Rolling Stone, Mayer expressed feeling humiliated and terrible by the song. He stated that he did not deserve the treatment he received and found it deeply hurtful.

In the following year, Mayer released a song called "Paper Doll," which was believed to be about his relationship with Swift. In the song, he sings the lyrics "And if those angel wings don't fly, someone's gonna paint you another sky," possibly alluding to the line in "Dear John" where Swift sings "You paint me a blue sky and go back and turn it to rain."

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‘The Story of Us,’ Speak Now (2010)

Swift previously revealed to USA Today that the inspiration behind both "The Story of Us" and "Dear John" was the same individual. She described "The Story of Us" as the experience of unexpectedly encountering her former partner at an awards show, where they were seated just a few seats apart. Swift expressed her inner desire to confront him, wondering if he felt the same anguish she did. However, she ultimately refrained from doing so due to the emotional barriers that existed between them.

The lyrics of the song extensively depict the aftermath of their uncomfortable encounter at the 2010 CMT Awards in June. Swift reflects on her current state of solitude in a crowded room, where they remain silent and distant. She yearns to understand if he experiences the same level of pain that she does.

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 her other songs which seem to be about Mayer, "Ours" presents a more positive perspective on their relationship. It portrays a couple whose love remains strong despite opposition from others. While this track could potentially refer to Swift's past romances with Taylor Lautner or Joe Jonas, the lyrics also bear a resemblance to Mayer's physical attributes. Swift sings about loving the space between a person's teeth and mentions tattoos, traits that Mayer possesses with a gap between his bottom front teeth and a sleeve of tattoos on his left arm.

‘Superman,’ Speak Now (2010)

Similar to her song "Ours," the lyrics of "Superman" from the deluxe edition of the Speak Now album contain a description that fans often associate with Mayer. In the song, Swift sings about someone who is "tall, dark, and beautiful," appearing to depict the physical attributes of the song's superhero.

‘I Knew You Were Trouble,’ Red (2012)

Swift discussed her history with Mayer in her fourth album, Red. During an interview on Good Morning America, she elaborated on the song "IKYWT," describing it as a reflection of self-frustration after experiencing heartbreak. Swift explains that despite noticing numerous warning signs when first encountering the individual, she still chose to pursue a relationship with them. The chorus of the song expresses remorse for not acknowledging the trouble this person brought into her life sooner.

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‘Would’ve, Could’ve, Should’ve,’ Midnights (2022)

More than ten years after the release of "Speak Now," Swift delivers one of her most scathing songs about Mayer on her tenth studio album, Midnight. In the chorus, she sings, "I would have never danced with the devil at nineteen. The painful truth is that it felt like heaven. Now that I'm grown, I'm haunted by ghosts. Memories feel like weapons, and knowing the truth, I wish I remained ignorant."

The song's most heartbreaking lyrics are found in the bridge, where Swift sings, "If death brings clarity, then why won't this pain end? We spent years tearing down our relationship, enjoying the thrill of hurting each other. Give me back my innocence, 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)

Although "Foolish One" was not included in the original Speak Now album, Swift released it as one of the vault songs on the album's July 2023 rerecording. Similar to "Dear John," Swift reflects on her and Mayer’s relationship, acknowledging her failure to recognize warning signs. She sings, "And I'll look back and regret how I ignored when they said, 'Run as fast as you can.'"

The lyrics also delve into Swift's post-breakup emotions, expressing her desire for reconciliation from Mayer. In the song, she states, "Foolish one, stop checking your mailbox for confessions of love that will never come. You will take the long way, you will take the long way down."