"Teardrops on My Guitar" is a song by American singer-songwriter Taylor Swift, taken from her self-titled debut album (2006). Swift wrote the song with Liz Rose, and Nathan Chapman produced it. Big Machine Records released "Teardrops on My Guitar" to US country radio on February 20, 2007, as the album's second US single. The song was released to US pop radio as a crossover single in November 2007. It was included on the international edition of Swift's second studio album, Fearless, and released in the UK in 2009.
Swift was inspired to write "Teardrops on My Guitar" by her unrequited love for a high-school classmate. Musically, the track is a gentle acoustic guitar-driven ballad and incorporates mandolin and fiddle. Music critics have conflicting opinions about the song's country-music classification; those disagreeing said it had a pop-music production. They complimented Swift's vocals and songwriting for earnestly portraying heartbreak. "Teardrops on My Guitar" peaked at number 13 on the Billboard Hot 100, and was Swift's first pop-radio crossover single on the Mainstream Top 40 chart. The single was certified triple platinum by the Recording Industry Association of America (RIAA).
The song's 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!". Swift performed the song live while supporting as the opening act for other country-music artists' concert tours, and included it on the set list of her first headlining tour, the Fearless Tour (2009–10).
Background and release
Swift was inspired to write "Teardrops on My Guitar" about her experience with a boy named Drew Hardwick, a classmate of hers whom she had feelings for. Hardwick later went on to join the United States Navy and was arrested for aggravated child abuse in 2015. During their freshman year at Hendersonville High School in Hendersonville, Tennessee, Swift and Hardwick sat beside each other in class every day. The two became friends, although Swift secretly desired for them to become a couple. Because of Hardwick's unawareness, he would frequently speak to Swift about another girl he had feelings for, something Swift pretended to be endeared by, commenting, "How beautiful she was, how nice and smart and perfect she was. And I sat there and listened, never meaning it any of the times I said, 'Oh, I'm so happy for you.'" Hardwick and his crush eventually developed a relationship that lasted for a few years. Swift never confessed her feelings to him. By the release of Taylor Swift, he remained unaware of Swift's intentions or of the song and continued his relationship with the same female. Upon its release as a single, Hardwick attempted to contact Swift via phone calls, which Swift did not respond to; he then left voicemails, but Swift felt too awkward to call back.
Two years after the album's release, as she was leaving her house to attend a Nashville Predators hockey game with Kellie Pickler and Carrie Underwood, Hardwick appeared at her driveway. A car parked and Hardwick and a friend of his came out of it. After two and a half years of not speaking, the two conversed: "He was like, 'Hey, how's it going?' And I'm like, 'Wow, you're late. Good to see you.' But we were civilized." Swift conjectured multiple theories as to why Hardwick appeared at her house. One of them was that he was attempting to prove to his friend that he was indeed the subject of "Teardrops on My Guitar". Other possibilities was that he wanted to rebuild their friendship or believed Swift was still pining away from him. Swift said it would have been poetic if he approached her upon the album's release and she would have accepted but that she had already moved on. Swift cited "Teardrops on My Guitar" as an example of how she expresses her sentiments in songs and sometimes in no other manner. She was not afraid of using Hardwick's first name on the track and, therefore, believed it was very honest and susceptible, something she adored.
"Teardrops on My Guitar" was released to US country radio on February 20, 2007, by Big Machine Records as the second single from Swift's debut album. Big Machine and Republic Records released the song to US contemporary hit radio in November 2007. The track was included on the non-US editions of Swift's second album, Fearless, released in March 2009. In the United Kingdom, "Teardrops on My Guitar" was released as a single on May 18, 2009, by Mercury Records.