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Our best wishes to the new couple, even if Di Caprio's dating habits are notoriously fickle.
But when it comes to sheer legacy, it's hard—nay, virtually impossible—to surpass his seemingly endless string of romances with the most beautiful women in the world. Don't feel too bad about Di Caprio's split from Bündchen, though, as the actor quickly moved on to another Victoria's Secret model, Bar Rafaeli.
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.
Their date wrapped up with a romantic bike ride to her place, we're told around 10 PM.