7. Alvy Singer in Annie Hall
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.