Taylor Swift has stated that she has written songs about all of her ex-boyfriends, and that they are the greatest inspiration for her. So this is a list of who was the inspiration for what song, what interviews she talked about it in, and any other relevant information.
- The song Tim McGraw was inspired by an ex-boyfriend named Brandon Borello. Their relationship ended because he had to go to college. Taylor told USA Today, “He bought the album [Taylor Swift] and said he really loved it, which is sweet. His current girlfriend isn’t too pleased with it, though.” It was named after a musician whose songs she liked. He was going away to college so she wanted to write him something to remember her by.
- Picture to Burn was written about an ex-boyfriend named Jordan Alford, whom she calls a redneck, and says he never let her drive his pick-up truck.
- Teardrops on My Guitar was written about a boy she liked, whom she never actually dated. “Drew was a real person!” she tells. Drew was surprised when he heard his name in the song. “I never knew she liked me” Drew says. Taylor stated that two years after the song came out Drew showed up at her house and asked her on a date. She declined. “It was the perfect fairytale ending but a little too late.”
- Should’ve Said No was about an ex-boyfriend that cheated on her. The boyfriend’s name was Sam Armstrong, and, in the CD booklet, every S, A, and M was capitalized if it was in the correct order.
|Joe Jonas||July 2008 – October 2008||Broke up over the phone for 27 secs. Inspired Forever & Always|
|Taylor Lautner||August 2009 – November 2009||Met on set of Valentine’s Day in her dressing room. Inspired Back To December|
|John Mayer||November 2009 – February 2010||Inspired Dear John|
|Jake Gyllenhaal||October 2010 – December 2010||Inspired We Are Never Ever Getting Back Together|
|Conor Kennedy||July 2012 – October 2012||Broke up due to long-distance issues.|
|Harry Styles||December 2012 – January 2013||Broke up due to heated argument with each other|
|Calvin Harris||March 2015 – June 2016|
|Tom Hiddleston||June 2016 – September 2016|