Conquests of a Serial Dater: John Mayer’s Sex Life Revealed

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4) Jessica Simpson August 2006 – May 2007

When John and Jessica became a couple in 2006, they had one of the juiciest relationships in Hollywood history. They first met on New Year’s Eve and kissed during midnight; J-Simps then followed him around on a Florida tour and they became official. They provided the paparazzi with an endless source of photographs and quotes about one another; reportedly Jessica helped him to come out of a shell and interact with other celebs and the media, as well as smoke marijuana and go clubbing. Mayer later gave an interview that said his love life with her was like sexual napalm, and that if she charged for the privilege he would sell all his stuff in order to remain in her bed. Finally they split, though both didn’t lack for green pastures afterwards.