It’s a Love Story!
See Taylor Swift’s Complete Dating History
Taylor technically never dated Drew. However, he was her first high school crush. She also wrote the song “Teardrops On My Guitar” about him in 2006.
Joe was Taylor’s first famous boyfriend, and he left a big scar on her heart. They were together from July until October 2008, when he dumped her over the phone!
Taylor and Lucas hit it off while filming the “You Belong With Me” video in 2009 but only hung out from March until April.
Taylor squared, if you will, hit it off in 2009 after working on the 2010 film Valentine’s Day together
John earned himself one of the most bitter songs ever, “Dear John,” after their tryst from December 2009 until February 2010.
Taylor and Cory never confirmed a relationship, though they both blushed like crazy when they were asked about it.
Jake and Taylor were super public about their relationship. They kissed, cuddled, held hands and went everywhere together from October through early December 2010
This is another unconfirmed relationship, but reports claimed they briefly dated from October 2011 to February 2012.
Taylor and Zac worked on The Lorax together, and fans speculated that they were dating in February and March of 2012. However, they both denied it.
Conor and Taylor were smitten with each other from July to October of 2012. They even had hot yacht makeout sessions!
Harry and Taylor allegedly only dated for a few months from December 2012 until January 2013, but clearly he left a mark on her heart.
Calvin will probably always be our fave boyfriend of Tay’s. He was sweet, low-key and actually her longest romance at the time, lasting over a year from February 2015 until June 2016.
Taylor and Tom were hot and heavy from June until September of 2016.
After years of failed romances, we’d love to see Taylor finally get her happily ever after with Joe.