In “Would’ve, Could’ve, Should’ve”, Taylor uses morbid and religious overtones in order to express regret for a youthful relationship that left her deeply scarred. This draws on themes such as those in previous songs “A Perfectly Good Heart” and “Dear John”, where the singer’s naivete was similarly trampled on.

“Would’ve, Could’ve, Should’ve” draws on Taylor’s relationship with John Mayer, which took place when she was nineteen and he was thirty-two. The age difference was highly criticized at the time, but the young Taylor stuck to her rebellious guns. Now, with more than a decade of experience accumulated since the end of the relationship, Taylor now regrets it, given its power imbalance, the untimely taking of her innocence, and the lasting trauma she maintains from it. She laments that she was enabled to leap too quickly into things she should have taken her time with.

The song itself is filled with heavy, threatening drums that provide a rock feel, juxtaposed with vocal background harmonies reminiscent of religious choirs. This combines to create an ominous track with sobering associations. Sonically, there is a somewhat comparable feel to Taylor’s earlier songs “Haunted” and “Don’t Blame Me”, albeit with a much different message.