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.
His next two girlfriends, Gisele Bündchen and Bar Refaeli, with whom Di Caprio shared his longest relationships, dated him while they were each 20 to 25 years old; Di Caprio was in his mid-to-late 20s and early-to-mid-30s, respectively.
In 2011, Di Caprio, then 36, dated 23- to 24-year-old Blake Lively.
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." ...