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Before Tom Brady, Gisele Bündchen dated Leo for five years, but ended it in 2005.

"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.

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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.

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." ...