Leo's 1995 rumored fling with Naomi Campbell reportedly fizzled fast, but they became good friends.
More than 20 years later, they still get together to look hot on vacation, save Russian tigers, and photobomb 50 Cent.
Things ended with Leo, and she moved on to costar Elijah Wood.
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From famous loves to quick hookups, to who is dating who, you will find all the celebrity dating history here.
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.