One Of Diane Keaton's Longest Relationships Was Also Her Most Controversial

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 world turned against him in the face of some disturbing allegations. When the #MeToo Movement initially began gaining traction, tons of netizens started thinking back to the timeline of Woody Allen's controversial relationship with his now-wife Soon-Yi Previn. 

They first met when Previn was just 10 years old and her stepmother, actor Mia Farrow, was dating Allen. Although the Oscar winner has been widely accused of grooming Previn, both parties maintain that their relationship only turned romantic when she turned 21. In 1992, Mia also alleged that Allen had molested their adoptive daughter, Dylan Farrow, when she was seven. In January 2018, Keaton took to X, formerly known as Twitter, to publicly defend her ex-boyfriend amidst these shocking resurfaced allegations. "Woody Allen is my friend and I continue to believe him. It might be of interest to take a look at the 60 Minute interview from 1992 and see what you think," she wrote at the time. 

After Diane Keaton died at the age of 79, in October 2025, a People source close to Woody Allen offered some insight into why she chose to stand by him amidst some pretty serious accusations. "She didn't believe that any problems [involving the allegations against Allen] overshadowed the important work that he did and the work they did together," the insider insisted. And that certainly seemed to be the case based on how the "First Wives Club" star publicly spoke about her controversial former partner. In a May 2014 interview with The Guardian, for instance, the Oscar winner praised Allen for maintaining a strong work ethic well into his 70s. Keaton also wasn't fazed by Dylan Farrow questioning her support of the controversial filmmaker in a 2014 New York Times article, arguing, "Who else are they going to drag in? They have to drag someone in."

Allen's support for Keaton remained similarly unwavering. While presenting the beloved star with her AFI Life Achievement Award, in 2017, he revealed that she had creatively fueled him ever since they first met and that Keaton even deserved credit for some of his greatest works. Meanwhile, in the "Manhattan" director's essay for The Free Press, Allen confessed that when he was dating his former co-star, he paid no mind to what the critics thought of his work, since, "As time went on I made movies for an audience of one, Diane Keaton." Ultimately, Keaton never got married for a good reason, despite having found love with many A-listers following her split from Allen.

If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN's National Helpline at 1-800-656-HOPE (4673).