Drew : the boyfriend she had freshman year that she wrote Our Song, and possibly Tim McGraw, about. Not the same Drew from Teardrops On My Guitar.
Sam : I’m guessing this was her second boyfriend. Should’ve Said No is about Sam.
Martin Johnson of Boys Like Girls : 2007. girls speculated for the longest time that Love Story was written about him. Other than that, I don’t know of any songs written about him. She wrote If This Was A Movie with Martin, as well.
Joe Jonas : 2008. the most popular of Taylor’s beaus in terms of songs written about him. Joe gets a whopping five songs written with him in mind, including Better Than Revenge. I believe they broke up sometime in the fall before Fearless was released – all I know for sure is that Forever and Always was a last minute edition to the track list of Fearless.
Taylor Lautner : 2009. the only boy who we know for sure has never had a nasty song written about him. Back To December is Taylor’s very first apology song. They broke up in December (obviously.)
John Mayer : 2010. second most popular, with four songs written about him (and all on the same album, at that.) From what I’ve come to understand, Taylor broke up with Taylor Lautner for John Mayer. John and Taylor first performed together in December, which is when Taylor Lautner was cut loose. Rumors of John and Taylor beginning to date began the following January in 2010. I have no ability to determine when exactly they broke up except to say that it was long enough before the release of Speak Now in October for her to pen out four whole songs about him.
Jake Gyllenhaal : just about immediately after Speak Now dropped, Jake and Taylor were seen out and about. They broke up in January – and apparently the entirety of Red is written about him.
Will Anderson : I don’t know anything about this to be honest with you, and no one else really does either. Rumors of them dating began in December 2011 and there’s no way to judge when they broke up. Begin Again is speculated to be about him.
Conor Kennedy : 18 year old high schooler.