Inside Diane Keaton’s Relationship With Woody Allen Over the Years

The late Diane Keaton was well-connected within the film industry, including her friendship with director Woody Allen.

A representative confirmed to People on Saturday, October 11, that the renowned actress passed away in California at the age of 79. As her fans reminisced about her iconic performances and her decision to embrace single motherhood in her 50s, many reflected on her well-known relationships with Al Pacino, Warren Beatty, and Allen, aged 89.

Keaton first crossed paths with Allen in 1969 during an audition for a role in his stage play Play It Again, Sam. They went on to collaborate in eight films over the years.

“He has always had a way with the ladies, you know,” Keaton shared in a 1996 interview with The New Yorker. “Women have always been attracted to him because he’s so witty and talented.”

Allen and Keaton were romantically linked for at least three years, continuing their professional collaboration in the years that followed. Keep reading to discover more about Diane Keaton’s relationship with Woody Allen.

Initial Encounter in 1969

Keaton was drawn to Allen when they met during her audition for Play It Again, Sam. In her conversation with The New Yorker in 1996, she openly expressed that she was “crazy about” him back then.

They Shared a Romantic Relationship

According to The New Yorker, Keaton and Allen were in a relationship for three years, although the Daily Mail mentioned in 2011 that their romance lasted five years.

They Collaborated on Eight Films

Over the years, Keaton and Allen worked together on eight films, including Annie Hall, the film version of Play It Again, Sam, Sleeper, Love and Death, Interiors, Manhattan, Radio Days, and Manhattan Murder Mystery.

In his 2020 memoir Apropos of Nothing, Allen reflected on their partnership, stating, “I still consult her on casting and any creative issues I encounter.”

Uncertainty Surrounding Annie Hall

Despite its acclaim and the fact that Keaton received an Oscar for Best Actress, Allen wasn’t fully confident in the film’s success.

Keaton revealed in 2017 to People, “He’s uproariously funny and I really adored him.” She added that Allen drew inspiration from their romance for the film.

“He was uncertain about the film’s potential,” she noted, elaborating, “He would say, ‘It’s just another sitcom.’ I knew it was a brilliant script.”

Keaton Supported Allen Amid Sexual Assault Allegations

In 2018, Keaton expressed her support for Allen on social media, defending him against persistent allegations of sexual misconduct.

The actress shared a segment from Allen’s 1992 60 Minutes interview, stating, “Woody Allen is my friend and I continue to trust him. It might be worth watching the 60 Minutes segment from 1992 to see what you think.”

Woody Allen Also Romanced Diane Keaton’s Sisters

Additionally, Allen had relationships with Diane’s sisters, Robin Keaton and Dory Keaton. “I became enamored with [Diane] and was also interested in her sisters and mother as individuals,” he recounted in his 1996 interview with The New Yorker.

In his 2020 memoir, he elaborated, saying, “I dated her gorgeous sister, Robin, and we had a brief romance. Following that, I dated her other beautiful sister, Dory, and we shared a little fling. The three Keaton sisters were all stunning, remarkable women with good genes.”