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,[3][4] 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.'"[5] 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.[5] 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.[6]