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An onlooker told the site that Leo was dressed casually in an orange sweater and tweed cap, while “there were two blondes and one brunette next to him.” We bet one of those blondes was While Leo looks like he’s getting hot and heavy with Kelly, it might be because his prior relationship with Rihanna, 27, fizzled right in front of him.

Apparently, the pop princess’ family were not fans of the 40-year-old.

More than 20 years later, they still get together to look hot on vacation, save Russian tigers, and photobomb 50 Cent.

Kristen Zang, a model who dated Leo for two years (1996-1998), accompanied the actor to the premiere of Romeo Juilet.

December 2010 - February 2011Back 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."We were just not meant to be boyfriend and girlfriend, but I respect him enormously, and I wish him nothing but the best," she told Access Hollywood in 2009.When Chris Brown and Rihanna got together back in 2008, it seemed like a match made in pop music heaven.All of Derek Jeter's past and present girlfriends, from serious relationships to fun and casual flings.Fans will also enjoy these TMI facts about Derek Jeter's sex life and sexy, shirtless photos of Derek Jeter.Things ended with Leo, and she moved on to costar Elijah Wood.