Teardrops on My Guitar

"Teardrops on My Guitar" is a song by the American singer-songwriter Taylor Swift from her debut studio album, Taylor Swift (2006). Big Machine Records released the song to country radio on February 20, 2007, and to pop radio on November 9, as the album's second single in the United States. In 2009, the track was released as a single in Europe and included on the "international" edition of Swift's second studio album, Fearless. Swift wrote "Teardrops on My Guitar" with Liz Rose. Inspired by Swift's feelings for a high-school classmate, the lyrics depict an unrequited love.

Nathan Chapman produced the track, which is a gentle acoustic guitar-driven ballad that incorporates mandolin, fiddle, electric guitar, and hushed steel guitar; the version released to pop radio features a drum loop. Despite its release to country radio, several critics disputed this genre categorization and considered it pop or soft rock. Reviews generally complimented Swift's vocals and songwriting for earnestly portraying teenage heartbreak. Retrospectively, critics have considered "Teardrops on My Guitar" a defining single for her early career.

In the United States, the single peaked at number 13 on the Billboard Hot 100 chart, reached the top 10 on the Pop Songs chart to become Swift's first pop crossover hit, and was certified triple platinum by the Recording Industry Association of America (RIAA). Elsewhere, it charted at numbers 45 in Canada and 51 in the United Kingdom. Trey Fanjoy directed the music video, which stars Swift as a heartbroken girl after learning that the boy in whom she is interested is dating another girl. Swift performed "Teardrops on My Guitar" on the Fearless Tour (2009–2010) and during various concerts of her later tours.