Her first of nine Top 20 hits, "Guitar" is about Taylor's real-life high school crush and how he had feelings for someone else. Told from her 16-year-old perspective, the song tackles the feeling of unrequited love.

Swift is saying sorry to a boy she may not have appreciated enough in 2009. "This is about a person who was incredible to me, just perfect to me in a relationship, and I was really careless with him," Swift told E! Entertainment. Swift wouldn't divulge who it was, but she dated Taylor Lautner toward the end of '09.

While Swift still chooses to neither affirm nor deny that this song is about John Mayer, we do know she had a short fling with the singer while lending her vocals for his 2010 track, "Half of My Heart."This particular story was inspired after Swift had a run-in with an ex at the 2010 CMT Music Awards.

From her Grammy-winning 2008 album "Fearless," this song portrays an unfaithful boyfriend who Taylor sees originally as the perfect guy in "Love Story." Swift dated Joe Jonas in 2008.

Don't make Taylor mad, whatever you do. From Swift's self-titled, debut album, the song easily writes off an old flame. The singer once explained about the song, "The storyline of the video is, if you break up with me, my band will ransack your house."