As half of country duo Love and Theft, Stephen Liles toured with Taylor in the early days. She wrote a song about him, but didn't tell him until just before it was released, on her second album. He later revealed that he had written one about her as well called, "Try to Make It Anyway." And yet...nothing happened. Kids today.
Song: "Hey Stephen" (2008)
Best lyric: "Hey Stephen I could give you fifty reasons why I should be the one you choose / All those other girls, well they're beautiful but would they write a song for you?"