Teardrops On My Guitar" is from Taylor's self titled album, Taylor Swift, following her debut single "Tim McGraw". The song is about a girl who is secretly in love with a boy, but the boy is interested in another girl. The song talks about the heartbreak of fancying someone who is so close but is out of one's reach.

The song debuted at number 93 on the Billboard Hot 100 in March 2007.

Radio stations along with GAC and CMT play an edited version of this song, with "I laugh 'cause it's so damn funny" changed to "I laugh 'cause it's just so funny."