“Teardrops on My Guitar” is a song by Taylor Swift from her self-titled debut album, Taylor Swift, released in 2006. It was the album’s second single and became one of Swift’s first major hits, helping to establish her as a rising star in country music.

Background and Theme

The song is about unrequited love and was inspired by Swift’s real-life experience with a high school crush named Drew Hardwick, who did not reciprocate her feelings. The lyrics detail Swift’s feelings of sadness and longing as she watches Drew with another girl.