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Leo began dating Kelly Rohrbach, a former prep schooler, D1 golfer, Georgetown University grad, and yes, Sports Illustrated model, in the spring of 2015. Leo and Rihanna apparently shared a "flirtatious" night in a Paris club in January, though tabloids reported the two had a fling going on long before. Rihanna denied it then—she was too busy to date anyone—but said if she had the time, her guy "would have to be man enough to live with my schedule and not get scared." ...

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Alanis recorded an album, Flavors of Entanglementas a result, so he has that going for him.While Accepted was not well received by critics, Lively's performance was, earning her a 'Breakthrough Award' from Hollywood Life.In 2007, she played one of the two title characters in Elvis and Anabelle as Anabelle, a bulimic girl who hoped to win a beauty pageant.Kristen Zang, a model who dated Leo for two years (1996-1998), accompanied the actor to the premiere of Romeo Juilet.Although a source told The New York Daily News that Kristen was "the love of his life," she dumped him because of his immaturity and "posse of young model-hounds."The daughter of singer John Phillips, Bijou dated Leo in 1998.

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