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In 2012, he dated 22- to 23-year old Erin Heatherton.

The actor had a literal May-December relationship with Toni Garrn, who Di Caprio dated from May 2013, when he was 38 and she was 20, to December 2014.

So much so that word among her friends is that she has her sights set on him becoming her boyfriend."Rihanna is no shrinking violet and unlike many of Leo's model girlfriends she's got 'a lot of game' to keep him on his toes."But the Diamonds singer is the first of many for heartbreaker, Leo, 40, whose Little Black Book must be full to the brim by now.So here's a look back at 10 of the hunk's most famous flings...RIHANNA Bajan beauty Rihanna is the latest in a long list of Leo's lovers.Leo, one of Hollywood's most well-known 'mama's boys,' took her advice and told Blake he needed his space.A close friend of Blake's is telling reporters she is devastated and "a total mess." LOL!

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Despite always being in the limelight, Karan Johar sure knows how to keep secrets.

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