"Teardrops on My Guitar" is a song by American country pop singer-songwriter Taylor Swift. The song was co-written by Swift, alongside Liz Rose and produced by Nathan Chapman with Swift's aid. "Teardrops on My Guitar" was released on February 24, 2007 by Big Machine Records, as the second single from Swift's eponymous studio album, Taylor Swift (2006). The song was later included on the international release of Swift's second studio album, Fearless (2008), and released as the third single from the album in the United Kingdom. It was inspired by Swift's experience with Drew Osenbach, a classmate of hers whom she had feelings for. He was completely unaware and continually spoke about his girlfriend to Swift, something she pretended to be endeared by. Years afterwards, Osenbach appeared at Swift's house, but Swift rejected him. Musically, the track is soft and is primarily guided by a gentle acoustic guitar. Some critics have queried the song's classification as country music.