Diane Keaton will always be hailed as a Hollywood legend. From her iconic performance in The Godfather to her comical ones in Annie Hall, Play It Again, Sam and Love and Death, the late Los Angeles, California, native left a lasting impact on the entertainment industry. While she is survived by her two children, Dexter and Duke Keaton, Diane never married, but her brief dating history includes some of the most famous actors from the 20th century.

One of Diane’s most well-known exes is Woody Allen, who penned a heartfelt tribute to his late friend and film collaborator after Diane died on October 11, 2025, at the age of 79.

“A few days ago the world was a place that included Diane Keaton. Now, it’s a world that does not,” Woody wrote in an essay published via The Free Press. “Hence, it’s a drearier world. Still, there are her movies. And her great laugh still echoes in my head.”

Hollywood Life is looking back at Diane’s short but sweet dating history below, from her first public relationship to her last.

Woody Allen

Woody and Diane dated in the early 1970s after first meeting at a 1969 audition. Though their relationship didn’t last, the former couple remained close friends and collaborators, having worked on several films together, including Play It Again, Sam, Sleeper, Love and Death and Annie Hall.

After Diane died in October 2025, Warren wrote an emotional tribute to his late friend in an essay published by The Free Press. In it, he briefly touched on the end of their romance, writing that “only God and Freud might be able to figure out” why they didn’t last as lovers.

“This beautiful yokel went on to become an award-winning actress and sophisticated fashion icon,” Woody added about Diane.

Al Pacino

Diane moved on with her The Godfather co-star Al Pacino. They had an on-again, off-again relationship until they wrapped filming The Godfather Part III. It’s unclear what exactly led to their split, but according to several reports, Diane gave Al an ultimatum: get married or break up.

According to Daily Mail, a friend of Al’s told the outlet that Diane was the love of his life, and that he always called her an “amazing woman” even after their split.

“I know he will forever regret he didn’t make his move when he had the chance,” the source told the outlet. “For years, after he and Diane split, Al used to say, ‘If it’s meant to be, it’s never too late for a do-over.’ But sadly, now it is.’

Warren Beatty

After she and Al called it quits for good, Diane moved on with Warren Beatty, her last public relationship. They never explained the reasons behind their breakup, but the former pair remained friends.

“I love her,” Warren told People in 2016 about his friend Diane. “She’s a combination of integrity and humor and intelligence and fairness and, did I say beauty? A brilliant comedic sense.”