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Let’s just take a look back at his former flames: Bridget Hall In 1994, the young up-and-coming actor dated model and cover girl Bridget Hall.Naomi Campbel Then, in 1995 the star dated the globally recognized supermodel and timeless beauty, Naomi Campbel.This is because the man looks like he was designed by a committee of goddesses whose only mission was to create a man that would be found invariably attractive around the world over the span of his lifetime by both men and women alike.Yes, it’s safe to say that the star has never been short of offers when it comes to beautiful women accompanying down the red carpet.

More than 20 years later, they still get together to look hot on vacation, save Russian tigers, and photobomb 50 Cent.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." ... Toni Garrn might want four kids, but her on-again, off-again boyfriend Leonardo Di Caprio may have his hands full with 20 models. In addition to Garrn, he's been romantically connected to supermodels Gisele Bundchen, Bar Refaeli and Erin Heatherton.Kristen Zang Next up was actress Kristen Zang, whom he had a brief romance with back in 1996.Gisele Bündchen Then, in 2003, Di Caprio started dating his long-time love, Brazillian model Gisele Bündchen.

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