Over nearly six decades in Hollywood, Diane Keaton and Woody Allen shared one of the most enduring—and complicated—friendships in film history. The Annie Hall star, who died at 79 on October 11, first met Allen in the late 1960s, sparking both a personal and professional connection that would define much of her career. Together, they created some of cinema’s most memorable moments, from Play It Again, Sam to Manhattan.

According to People, a source close to Allen revealed that he was “extremely distraught and surprised” by Keaton’s death, adding that the news left him reflecting on his own mortality. Despite the ups and downs of their relationship—both on screen and off—the two remained close friends long after their romance ended. “He appreciated her very much,” the source said, noting t

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