8. Jessica Simpson
One of Mayer’s most renowned couplings was with pop princess Jessica Simpson. They dated from 2006 to 2007, but drew more publicity in 2010 when Mayer decided to “kiss and tell” some inappropriate details about their relationship. In a famous interview, he said, “Sexually it was crazy…It was like napalm, sexual napalm. Yeah, that girl is like crack cocaine to me.” Jessica, who had a good girl reputation at the time, wasn’t pleased about having her sexual prowess being blabbed about – even if most people would take it as a compliment.
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