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

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2) Vanessa Carlton July 2002 – 2003

These two singers rose to prominence around 2003 when both had smash hits; Carlton’s song “A Thousand Miles” hit the top of the charts at the same time that Mayer’s hit “No Such Thing” was a mainstay on the radio. Like many relationships before and after, however, Carlton and Mayer split. She called him a bad breakup, then would later go on to declare that she was bisexual.