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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.
While it's clear he has a thing for Jennifers (he was engaged to one and married the other), he also has a habit of dating his costars.
Things ended with Leo, and she moved on to costar Elijah Wood.
Before Tom Brady, Gisele Bündchen dated Leo for five years, but ended it in 2005.
Of course, that doesn’t mean he’s been single, either!
For months, the actor has been dating his former co-star Vanessa Kirby — and Tom Cruise and his girlfriend could be getting married in the future.