Jessica's Many Men
Credit: MICHAEL CAULFIELD/WIREIMAGE.COM
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John Mayer
When she began dating the "Heartbreak Warfare" crooner in Jan. 2007, Simpson famously darkened her locks before calling it quits in May. Earlier this year, Mayer opened up about their relationship, saying that being with Simpson was like "sexual napalm" and that she was "like crack cocaine to me."