Hidden Message: He Will Never Know
Swift’s second single, Teardrops On My Guitar, was released February 24, 2007. The song was inspired by Taylor’s high school crush Drew Hardwick. The two never dated; Hardwick saw Swift as a friend and a go-to girl for advice about his actual relationship. Drew is well aware the song was written about him. Swift is quoted saying, “My dad was all "Taylor there are two guys coming up the driveway." I looked and it was Drew! I guess this was the whole "I know the song is about me, still interested?" I mean if he hears the song and heroically shows up, I mean that's great, but two years later. You're a little late!” Drew is now married (and not to the girl from the song).
Sources: 1, 2, 3