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."