What's weird about this situation is that, unlike other instances on this list, Woody Allen actually did date Diane Keaton, fulfilling the slumdog millionaire prophecy both on screen and in life. I love Woody Allen. Though not all of his films are masterpieces (and given the fact that he's made a million, how could they be?), when this man is on, he's an unstoppable force. In his magnum opus Annie Hall, Woody's Alvy Singer manages to land himself in a relationship with cinema's quintessential manic pixie dream girl, the titular Annie Hall. Of course, Alvy also had sex with Shelly Duvall, so it's kind of a wash.