The release of Taylor Swift's re-recorded album, "Speak Now (Taylor's Version)", has revived discussions surrounding her rumored relationship with John Mayer, particularly the song "Dear John." The re-recording, released on July 7th, revisits the emotions Swift experienced at the time of the original 2010 album's creation.

While never officially confirmed, Swift and Mayer collaborated musically in 2009, performing together several times after working on Mayer's song "Half of my Heart." This collaboration originated from a tweet by Mayer expressing his desire to work with the then 19-year-old Swift.

Following their alleged romance, both artists released songs perceived as breakup anthems. Swift's "Dear John" from the original "Speak Now" album, released in 2010, contained lyrics that many interpreted as referencing Mayer, such as, "Don't you think nineteen is too young / To be played by your dark twisted games / When I loved you so?" While Swift has never explicitly confirmed the song's subject, she did allude to the cathartic nature of songwriting in a past interview with People magazine, describing putting a song on an album as akin to finally sending an unsent email.

In a 2012 Rolling Stone interview, Mayer addressed "Dear John," expressing feeling humiliated and blindsided by its release. He criticized the songwriting, calling it "cheap" and claiming he never received any direct communication from Swift about the song's content.

Swift recently performed "Dear John" live for the first time in over a decade during her "The Eras Tour," after not playing it since the conclusion of her "Speak Now" tour in 2012. Prior to performing the song, Swift addressed her fans, emphasizing the importance of kindness online and stating that she re-released the album to own her music, not to incite online battles over past relationships.

Swift has acknowledged a pattern of placing emotionally vulnerable songs as the fifth track on her albums, with "Dear John" being one example. Pop culture expert Rob Weiner highlighted the significance of Swift's Track 5 phenomenon, emphasizing how her vulnerability creates a deeper connection with her audience.