Swift

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 Navy. During their freshman year of high school at Hendersonville High School, Swift and Hardwick sat beside each other in a class everyday. The two developed a fond friendship, although Swift secretively desired for it to become a romantic relationship. Because of Hardwick's unawareness, he would frequently speak to Swift about a 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 love interest eventually developed a relationship which 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 the song and continued his relationship with the same female. Upon "Teardrops on My Guitar"'s 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.

- Tyler Hilton

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, out of it, exited Hardwick and a friend of his. 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 amend 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.

Source : http://en.wikipedia.org/wiki/Teardrops_on_My_Guitar