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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 19, 2007 by Big Machine Records, as the second single from Swift's eponymous debut studio album (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 Hardwick, a classmate of hers for whom she had feelings. He was completely unaware and continually spoke about his girlfriend to Swift, something she pretended to be endeared by. Years afterwards, Hardwick appeared at Swift's house, but Swift rejected him. Musically, the track is soft and is primarily guided by a gentle acoustic guitar. Critics have queried the song's classification as country music, with those in agreement (such as Grady Smith of Rolling Stone) citing the themes and narrative style as country-influenced and those opposed (such as Roger Holland of Popmatters) indicating the pop music production and instrumentation lack traditional country elements.

Critics received the track generally positively, complimenting Swift's vocal delivery and songwriting style. The song is considered to be Swift's breakthrough single, as it spread her popularity throughout the United States. "Teardrops on My Guitar" was commercially successful, peaking at number 13 on the Billboard Hot 100, becoming the best-charting single from Taylor Swift on the chart, and being Swift's debut entry on the Billboard Year-End Hot 100 charts. The single was also certified triple platinum by the Recording Industry Association of America (RIAA). Its music video was directed by Trey Fanjoy and features Swift as she sees her love interest develop a relationship with another female. The video received a nomination for MTV Video Music Award for Best New Artist, but lost to Tokio Hotel's music video for "Ready, Set, Go!". The song was promoted through multiple live performances, some while supporting as opening act for various country artists' concert tours. She also performed "Teardrops on My Guitar" on her first headlining tour, the Fearless Tour (2009–10).

Chart performance

On the week ending March 24, 2007, "Teardrops on My Guitar" debuted at number ninety-three on the Billboard Hot 100. "Teardrops on My Guitar" is also Taylor Swift's first song to debut on the Billboard Year-End Hot 100 charts. After thirty-seven weeks upon the chart, on the week ending March 1, 2008, the song reached its peak at number thirteen, becoming the highest-charting single from Taylor Swift on the chart. On the week ending May 17, 2008, the song spent its last week on the Billboard Hot 100 at number forty-nine, after a total of forty-eight weeks on the chart. The single was certified triple platinum by the Recording Industry Association of America in April 2014. As of November 2014, "Teardrops on My Guitar" has sold 2.9 million copies in the United States.

On Billboard Hot Country Songs chart, "Teardrops on My Guitar" debuted at number forty-six on the week-ending February 24, 2007. The song entered the top ten at number eight on the week-ending July 14, 2007, and on its twenty-sixth week on the chart, the week-ending August 18, 2007, it reached its peak at number two on the Billboard Hot Country Songs. The track spent a total of twenty-five weeks on Hot Country Songs. "Teardrops on My Guitar" was a crossover hit as well, peaking at number seven on Billboard Pop Songs and spending twenty-one weeks on the chart.

"Teardrops on My Guitar" is considered to be Swift's breakthrough single, as it spread her popularity throughout the United States. In Canada, the song peaked at number forty-five on the week ending August 18, 2007. The single was certified platinum by Music Canada for sales of 80,000 digital downloads. Released as the third single from Swift's second studio album Fearless (2008), the track debuted at number one hundred on the week ending April 27, 2009 and peaked at number fifty-one on the week ending May 23, 2009 in United Kingdom.