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. Swift and Hardwick sat beside each other in a class everyday. 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.’” Hardwick and his love interest eventually developed a relationship which lasted for a few years. Swift never confessed her feelings to him.