Ryan Phillippe and Rihanna
Ryan Philippe and Rihanna reportedly hooked up for a short time in 2011, though it appears it was more of a fling than a relationship.
"They initially hooked up when things were strained with [Rihanna's ex] Matt Kemp back in early December," a source told E! of their hookup in February 2011. "She thinks he's hot. They totally had sex. And it wasn't even the first time!"
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