Diane Keaton's relationship history is a who's who of Hollywood icons, which notably features one disgraced figure. When the beloved actor auditioned for a role in Broadway's "Play It Again, Sam," in 1969, her path crossed with its writer's, Woody Allen. In an October 2025 essay for The Free Press, the divisive filmmaker gushed that Keaton floored everybody in the room with her acting chops and stole his heart with her charming personality to boot. The "Annie Hall" director revealed that he fell hard and fast for his Broadway co-star when they chatted over a meal during their break too. Although the couple split up after just a couple of years of dating, they remained professional collaborators and close friends. In fact, the "Godfather" star stayed firmly in Allen's corner when the wor

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