Woody Allen Remembers His Old Love Diane Keaton
The longtime filmmaker — who dated the late actress in the early 1970s — was said to have been distraught when he heard the news of her passing. He looked back on their relationship in a personal essay.
Diane Keaton, the beloved star of "Annie Hall" and "The Godfather" films, passed away on Saturday, October 11, 2025, leaving Hollywood and her fans alike reeling in unprecedented grief.
Diane Keaton attends the Handprint and Footprint in Cement Ceremony for Actress Diane Keaton hosted by TCL Chinese Theatre on August 11, 2022, in Hollywood, California. | Source: Getty Images
Among those mourning the actress is her former partner turned longtime friend, director Woody Allen. The pair worked on numerous films together, but none were more famous than Allen's romantic comedy, "Annie Hall," in which Keaton played the titular character.
A source told People that Allen was "extremely distraught and surprised and upset" about Keaton's death, adding that "it makes him think of his own mortality." The two remained good friends following the end of their romance for nearly six decades.
Diane Keaton and Woody Allen in the film "Annie Hall," circa 1977. | Source: Getty Images
"He appreciated her very much," the source said of Allen, adding that was unaware of Keaton's declining health. "Nobody seemed to know. He was surprised." Allen and Keaton first met when she auditioned for his play, "Play It Again, Sam," in 1969.
"For the first week of rehearsal we never spoke a word to one another. She was shy, I was shy, and with two shy people things can get pretty dull," Allen wrote in a personal essay on The Free Press, published Monday, October 13.
Woody Allen and Diane Keaton as Boris and Sonja in the comedy film "Love and Death," circa 1975. | Source: Getty Images
One day, they happened to take a break at the same time and decided to visit a local fast-food joint together. The outing marked the beginning of lifelong companionship. "The upshot is that she was so charming, so beautiful, so magical, that I questioned my sanity," Allen continued.
"I thought: Could I be in love so quickly?" By opening night that same year, the pair had fallen in love and begun dating. Allen then began showing Keaton his films privately before having them released publicly.
Wody Allen and Diane Keaton are seen on June 20, 1970, in New York City. | Source: Getty Images
One of the first films he showed her was his 1969 crime-comedy "Take the Money and Run." Allen said he prepared himself for the worst review, but Keaton found it "very funny and very original."
"Its success proved her correct and I never doubted her judgment again. I showed her every film I made after that and grew to care only about her appraisals," he said. Eventually, their romance ran its course.
"We had a few great personal years together and finally we both moved on, and why we parted only God and Freud might be able to figure out," Allen said. "She went on to date a number of exciting men, all of them more fascinating than I was."
Woody Allen leans his head on the shoulder of Diane Keaton in a scene from "Love and Death," circa 1975. | Source: Getty Images
Indeed, Keaton went on to have high-profile relationships with Al Pacino and filmmaker Warren Beatty. Allen also moved on with actress Mia Farrow. The former couple had a highly publicized split following Allen's affair with Farrow's adopted daughter, Soon-Yi Previn.
In a 1993 testimony during the custody battle for their daughter Dylan, Farrow claimed that in 1992, Dylan told her Allen had touched her in a sexual manner. Allen has repeatedly denied the allegation, and he later married Previn in 1997.
The allegations were reignited amid the #MeToo movement in 2018, during which Allen faced renewed backlash. Keaton defended the director, even writing on X that year, "Woody Allen is my friend and I continue to believe him."