Taylor wrote this song about Stephen B. Liles from the country music duo Love And Theft (an opening act on her Fearless Tour in 2008). She talked about it in a interview in 2008:

"This is a guy I had a crush on. I wrote about all these reasons he should be with me instead of other girls (…). This guy has absolutely no idea I had a crush on him. It’s gonna be kind of interesting when he finds out."

Little did Taylor know, Stephen returned her feelings — he even wrote a song for her called “Try To Make It Anyway!”