This song is about Taylor Swift's best friend, Abigail. Swift told The Los Angeles Times October 26, 2008 that for most of their time in high school, the two friends thought of themselves as ugly ducklings. She explained: "We kind of came to the conclusion in ninth grade that we were never going to be popular, so we should just stick together and have fun and not take ourselves too seriously. That's why I had so much fun in high school, because I didn't focus too much on the fact that I wasn't really in the clique."
Swift admitted to CMT Radio that she cried when she recorded this song. She explained: "I'm not likely to cry over something I've gone through, even if it's the worst breakup ever. Maybe I haven't had that breakup yet. Maybe there will be a breakup where I'll just cry every time I think of it. (laughs) But the things that make me cry are when the people I love have gone through pain and I've seen it. "Fifteen" talks about how my best friend, Abigail, got her heart broken when we were in ninth grade and singing about that absolutely gets me every time."
Swift told That's Country that she "started everything with the line 'Abigail gave everything she had to a boy who changed his mind' and wrote everything else from that point, almost backwards."
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