Would've, Could've, Should've

Album: Midnights (3am Edition) (2022)
Charted: 20
Play Video

Songfacts®:

  • Here, Taylor Swift expresses regret for an age-gap relationship that went down when she was 19.

    I would've stayed on my knees
    And I damn sure never would've danced with the devil
    At 19


    Over a decade later, the memories still haunt her and she recognizes how the amorous association affected her personal development.
  • Taylor Swift included "Would've, Could've, Should've" on the 3am Edition of Midnights. As soon as she dropped the track, fans buzzed that she's calling out singer-songwriter John Mayer, whom she reportedly dated during the 2009 - 2010 winter. Swift was 19 and Mayer 32 when they got together.

    It's generally believed the singer's equally scathing Speak Now track "Dear John" is also about Mayer.
  • When Swift released Midnights, her fans noted that Jack Antonoff served as co-producer on all 13 tracks and her chief Folklore and Evermore collaborator Aaron Dessner wasn't involved. But on the 3am Edition, "Would've, Could've, Should've" is one of three bonus tracks featuring co-writes with Dessner.
  • Taylor Swift played "Would've, Could've, Should've" live for the first time at Nashville's Nissan Stadium on May 8, 2023. She was joined on stage by Aaron Dessner, who she described as a "kind, wonderful, genius."

Comments: 1

  • AnonymousI love this song so flippin much.
see more comments

Editor's Picks

Crystal Waters

Crystal WatersSongwriter Interviews

Waters tells the "Gypsy Woman" story, shares some of her songwriting insights, and explains how Dennis Rodman ended up on one of her songs.

P.F. Sloan

P.F. SloanSongwriter Interviews

P.F. was a teenager writing hits and playing on tracks for Jan & Dean when he wrote a #1 hit that got him blackballed.

Part of Their World: The Stories and Songs of 13 Disney Princesses

Part of Their World: The Stories and Songs of 13 Disney PrincessesSong Writing

From "Some Day My Prince Will Come" to "Let It Go" - how Disney princess songs (and the women who sing them) have evolved.

Harry Shearer

Harry ShearerSongwriter Interviews

Harry is Derek Smalls in Spinal Tap, Mark Shubb in The Folksmen, and Mr. Burns on The Simpsons.

Joe Elliott of Def Leppard

Joe Elliott of Def LeppardSongwriter Interviews

The Def Leppard frontman talks about their "lamentable" hit he never thought of as a single, and why he's juiced by his Mott The Hoople cover band.

Gary Brooker of Procol Harum

Gary Brooker of Procol HarumSongwriter Interviews

The lead singer and pianist for Procol Harum, Gary talks about finding the musical ideas to match the words.