Zimbio, in photo: Ryan Phillippe, Rihanna
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December 2010 - February 2011

Back when Ryan Phillippe was linked with Amanda Seyfried, he was rumored to also have a short fling (hookup) with Rihanna. Sources said they'd been "very casual" and "discreet," but had been hooking up for a few months since December 2011. After a supposed sleepover after a February party, rumors of the two stopped.