"Teardrops on My Guitar" is the second single by country pop artist Taylor Swift. This work 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 named Drew, but Drew is interested in another girl. The song talks about the heartbreak of liking someone who is so close but is out of one's reach. Swift also states that it's about the conflicting feelings of loving someone and wanting them to love you back and wanting them to be happy. In a behind-the-scenes video, Swift reveals that the song was written about a classmate.

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

Country radio stations along with GAC and CMT play a remixed version of this song, with "I laugh 'cause it's so damn funny" changed to "I laugh 'cause it's just so funny." The instrumentation is different between the single and album versions of the song, as well.

A new remix of the song, with a drumloop added and the banjo removed, was released to Top 40 and Adult Contemporary radio in October 2007 and began charting in both formats soon after. The song has reached a new peak on the Pop 100 at number 11. The song re-entered the Hot 100 at 44. The song ties Carrie Underwood's hit song "Before He Cheats" as the longest charting song before cracking into the top 15 on the Billboard Hot 100 at 33 weeks.