John Mayer: December 2009 - February 2010

Taylor and John Mayer had a highly scrutinised relationship in 2009 when she was 19 and he was 32.

Though brief, the romance reportedly ended on bad terms, with John later saying he was “really humiliated” by her song Dear John.

Taylor never publicly confirmed the track was about Mayer, but fans and critics believe they have connected the dots.