
Says Swift: "'Picture To Burn' has an 'angry and I'm-done-with-him attitude,' while 'Should've Said No' is "more of a moral statement. Swift compared this to another one of her songs, Picture to Burn. Swift has also said that many of the lyrics were based on actual words that she used when confronting her then-boyfriend.

The first line that came to her was the title, and she wrote the chorus in five minutes. According to Country Weekly magazine, she was inspired to write it after she discovered that her boyfriend at the time had cheated on her. Taylor Swift wrote the song when she was sixteen years old. The song is an up-tempo in which the central character addresses a former lover who has cheated on her, telling him that he "should've said no" to the female who has taken her place in his life ("You should've said no/You should've gone home/You should've thought twice before you let it all go/You should've known that word 'bout what you did with her would get back to me").
