This cheating number was one of three tracks on the album that Swift wrote on her own. The teenage Country star penned this song a week before her final recording.
This comes from an unfortunate chapter in Swift's life. She explained: "I wrote this song by myself, and it literally took me just 20 minutes to write before we recorded it. I was living every line in this song at the time. I wrote this song about a guy who cheated on me who shouldn't have."
Swift compared this to another of her songs that concerns a relationship which went wrong: " Picture To Burn." 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. It's an 'I love you, we were awesome and great together, but you messed this up and I would still be with you' kinda thing. You said yes, and you should've said no."
When this song reached the Top 10 of the Hot Country Songs in July 2008, Taylor Swift became the first solo female artist to score five top 10 hits from a debut album since the album chart was first published in 1964. Her previous four chart entries had been " Tim McGraw," " Teardrops on My Guitar," " Our Song" and " Picture To Burn."