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

Mike Campbell

Mike CampbellSongwriter Interviews

Mike is lead guitarist with Tom Petty & the Heartbreakers, and co-writer of classic songs like "Boys Of Summer," "Refugee" and "The Heart Of The Matter."

Donny Osmond

Donny OsmondSongwriter Interviews

Donny Osmond talks about his biggest hits, his Vegas show, and the fan who taught him to take "Puppy Love" seriously.

Carl Sturken

Carl SturkenSongwriter Interviews

Hitmaker Carl Sturken on writing and producing for Rihanna, 'N Sync, Christina Aguilera, Kelly Clarkson, Donny Osmond, Shakira and Karyn White.

American Hits With Foreign Titles

American Hits With Foreign TitlesSong Writing

What are the biggest US hits with French, Spanish (not "Rico Suave"), Italian, Scottish, Greek, and Japanese titles?

Mick Jones of Foreigner

Mick Jones of ForeignerSongwriter Interviews

Foreigner's songwriter/guitarist tells the stories behind the songs "Juke Box Hero," "I Want To Know What Love Is," and many more.

The Police

The PoliceFact or Fiction

Do their first three albums have French titles? Is "De Do Do Do, De Da Da Da" really meaningless? See if you can tell in this Fact or Fiction.