Zimbio, in photo: Kim Kardashian, boyfriend Ray J
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14. Kim Kardashian dated Ray J
2005 - 2007

Kim Kardashian first met Ray-J while she was working as a stylist for his sister, Brandy. The two are said to have been on and off again for nearly three years before things ended for good. In 2007 their split got really messy when a sex tape they made was picked up for distribution by Vivid Entertainment. At first Kim denied rumors of the tape's existence, but later settled with Vivid for $5 million.