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

David Sancious

David SanciousSongwriter Interviews

Keyboard great David Sancious talks about his work with Sting, Seal, Springsteen, Clapton and Aretha, and explains what quantum physics has to do with making music.

Kiss

KissFact or Fiction

Kiss is the subject of many outlandish rumors - some of which happen to be true. See if you can spot the fakes.

John Lee Hooker

John Lee HookerSongwriter Interviews

Into the vaults for Bruce Pollock's 1984 conversation with the esteemed bluesman. Hooker talks about transforming a Tony Bennett classic and why you don't have to be sad and lonely to write the blues.

Max Cavalera of Soulfly (ex-Sepultura)

Max Cavalera of Soulfly (ex-Sepultura)Songwriter Interviews

The Brazilian rocker sees pictures in his riffs. When he came up with one of his gnarliest songs, there was a riot going on.

Grunge Bands Quiz

Grunge Bands QuizMusic Quiz

If the name Citizen Dick means anything to you, there's a chance you'll get some of these right.

Tony Banks of Genesis

Tony Banks of GenesisSongwriter Interviews

Genesis' key-man re-examines his solo career and the early days of music video.