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

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6) Jennifer Aniston

Proof positive that any woman can get over getting dumped by Brad Pitt, John and Jennifer appeared together first when she was filming a movie in Florida. The two went to red-carpet events and garnered their fair share of photographs. They were together for over a year but split because of, among other things, Jennifer’s experience rising to stardom in the 1990s — Mayer said she didn’t know how to handle things like TMZ and Twitter.