2005 — Taylor dates Brandon Borello, a senior, during her freshman year of high school. The relationship ends when he goes off to college, but she goes on to write three songs about him including “Tim McGraw,” and “Our Song,” he is flattered. ”He bought the album and said he really loved it, which is sweet. His current girlfriend isn’t too pleased with it, though.”
2008 – Taylor begins her first Hollywood romance with Joe Jonas, but their courtship ends just months later when Joe reportedly dumped Taylor for his “Lovebug” video chick Camilla Belle during a 27 second phone conversation.
November 2009 — Taylor and Taylor Lautner break up after a brief relationship, although it remains unclear if they were ever actually dating. A source tells PEOPLE, “the media made way more out of it than it is.” However, the song “Back To December” was reportedly Taylor’s apology to Taylor L. about their break up.
December 2010 — Taylor and Jake Gyllenhaal end their romance after just two months.
January 2011 — Taylor and Jake reunite for a dinner date, but nothing comes of it and they stick with their original plan to go
their separate ways.
Early December 2012 – Taylor and Harry go public with their romance during a date in New York City at the Central Park Zoo.
January 4, 2013 — Taylor and Harry break up after a romantic vacation in Virgin Gorda gone wrong. According to reports, the two got in a fight a couple of days into their getaway and in result, Taylor returned to the states sans Harry.
”Taylor Swift Spotted on Boat Without Harry Styles Amid Breakup Reports.” E! Online. N.p., n.d. Web. 10 May 2013.
“Taylor Swift.” Boyfriend & Dating History. N.p., n.d. Web. 10 May 2013.
”Taylor Swift.” Taylor Swift. N.p., n.d. Web. 11 May 2013.