Taylor Swift is a mastermind. She said so herself on the 13th track of Midnights, her 10th studio album out today (October 21), and she reaffirmed it with Midnights (3am Edition) in the middle of the night, giving fans seven additional songs to try and digest. One of them is “Would’ve, Could’ve, Should’ve,” and the seemingly on-point fan theories are flying.
The early belief is that “Would’ve, Could’ve, Should’ve” is about John Mayer. The clues are strong. The song is No. 19 on the tracklist. The torching chorus finds Swift lamenting, “I would’ve stayed on my knees / And I damn sure never would’ve danced with the devil / At nineteen.” Who was Swift linked to when she was 19 years old? Mayer, who was 32 then. They reportedly dated briefly between 2009 and 2010.
“Would’ve, Could’ve, Should’ve” wouldn’t be the first Mayer-adjacent track in Swift’s discography. Track five of her October 2010 album Speak Now was titled “Dear John” and similarly cites a toxic situationship from her 19th year in the chorus: “Dear John, I see it all now, it was wrong / Don’t you think nineteen’s too young / To be played by your dark, twisted games when I loved you so?”
Elsewhere on Midnights, Swiftie sleuths have spotted a 30 Rock reference and a mysterious voice on “Midnight Rain.” And while all signs indicate another reflection on a regrettable involvement with Mayer, the more important question is whether Swift coyly confirmed an engagement to Joe Alwyn, her boyfriend of six years, in the first verse of “Sweet Nothing.” She co-wrote the Midnights song with William Bowery, Alwyn’s pseudonym, and the first verse might allude to an engagement ring: “I spy with my little tired eye / Tiny as a firefly, a pebble / That we picked up last July / Down deep inside your pocket / We almost forgot it.”
Midnights is out now via Republic. Get it here.
