You might remember John Mayers controversial interview with Playboy in 2010 where he dished out a few too many revealing details about his relationship with Jessica Simpson. The pair dated from 2006 to 2007. Mayer went on to date Jennifer Aniston from 2008 to 2009. Mayer and Taylor Swift were romantically linked in 2009. Shortly after the couple split, Swift released Dear John on her 2010 album Speak Now, which was allegedly written about Mayer.