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.’” 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.