Swift performed " Should 've Said No " at the 2008 Academy of Country Music Awards ; footage from the performance was later used as a live music video for the song . This performance begins with a hooded Swift playing the guitar and after an on-stage costume change , she is wearing a black dress . At the end of the performance , Swift walks up the stairs and performs in the rain . She also performed the song with Jonas Brothers on the Burning Up Tour . As for her own concerts , " Should 've Said No " was performed as the encore for both the 2009 and 2010 set lists of her first concert tour , Fearless Tour . She performed the song , acoustically , on selected dates of her Red Tour , in place of " I Almost Do " ; and it replaced " You Are in Love " during the first show in Santa Clara during The 1989 World Tour . The song was recently put on the original set-list of Swift 's Reputation Tour , where it was performed in a mashup with " Bad Blood "
The 1989 World Tour
The 1989 World Tour
Should've Said No