A Not-So-Brief History of All the Ladies Leonardo DiCaprio Has Dated

Leo and Naomi are close friends, yes, but it's long been reported that he and the supermodel hooked up back in the day (1995, to be exact) and decided to just keep things platonic. Over the years, they've gone on vacations together with their group of mutual friends and have hosted — and attended — each other's charitable events. Oh, and he's also photobombed her selfie with 50 Cent.