Friday, July 3, 2026

Exclusive: Woody Allen Dated Diane Keaton and Each of Her Sisters, Plus He Addresses His Reputation for an “Obsession Dating Younger Women”

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There is so much in Woody Allen’s rich 400 page memoir, you will not be able to put it down. A good read? The best. I can’t imagine that “Apropos of Nothing” will not be a run away hit. Hachette really made a mistake cancelling it. Skyhorse/Arcade gets a windfall here. So many times I’ve laughed out loud reading — I mean, really laughing. There are great lines and great anecdotes.

Everyone will focus first on “Apropos of Nothing” on the Mia Farrow stuff. Woody writes so lovingly of Mia and her mother, of Mia’s acting in his films. There is no rancor of kind until, of course, their relationship unravels. But he’s very praising of her acting talents, and his memories of their early relationship are terrific.

But one thing that did surprise me about Woody and his personal life: he not only lived with Diane Keaton, he dated each of her sisters. Romance, fling. That’s how they are respectively described.  He doesn’t say this somehow inspired “Hannah and Her Sisters.” But really, this is “Diane and Her Sisters.” They have all remained friends.

He writes of Keaton, who won the Oscar for his film, “Annie Hall”:

We parted company as friends and, as I’ve said, have
remained close down through the years. I still consult her
on casting sometimes or any creative problems I might be
struggling with. We never fought and would work together
many times in the future. In time I dated her beautiful sister,
Robin, and we had a brief romance. After that I dated her
other beautiful sister, Dory, and we had a little fling. The
three Keaton sisters were all beautiful, wonderful women.
Good genes in that family. Award-winning protoplasm.
Great-looking mother. Mandelbrot’s similarity hitting the
jackpot.

Woody also dispels the idea that he’s only been interested in younger women.

“Of the many women I have been
involved with over the decades, almost none were much
younger than I was. One of them, I wasn’t even involved
with. I merely invited her on a trip I was taking to Paris.
She turned me down, and that ended it.”

His classic movie, “Manhattan,” infamously chronicles a relationship with an 18 year old, played by Mariel Hemingway. Woody was 42 then. In 1979, when it was released, no one cared. Today, it’s the subject of much discussion. The character was based on a brief relationship he had with Stacey Nelkin, who went on to marry actor Barry Bostwick (15 years her senior, by the way).

“When I fell in love with Soon-Yi,
Manhattan was revived and I suddenly got a reputation as
someone obsessed with young women. I was obsessed with
gangsters, baseball players, jazz musicians, and Bob Hope
movies, but young women have been a tiny fraction of the
women I dated over the decades. I have used the May-
December ploy as a comic and romantic theme a few times,
just as I have used psychoanalysis or murder or Jewish
jokes, but only as good material for plots and laughs. Still,
it’s a juicier headline than “Man Dates Age-Appropriate
Woman.”

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Roger Friedman
Roger Friedman
Roger Friedman is the founder and editor-in-chief of Showbiz411. He wrote the FOX411 column on FoxNews.com from 1999 to 2009, where he covered Michael Jackson, and previously wrote the "Intelligencer" column at New York magazine in the mid-1990s, where he covered the O.J. Simpson trial. He also edited Fame magazine. His bylines have appeared in The New York Times, The Washington Post, the New York Daily News, the New York Post, Vogue, Details, and the Miami Herald. He is a voting member of the Critics Choice Awards (Film and Television branches), and his movie reviews are tracked by Rotten Tomatoes. With D.A. Pennebaker and Chris Hegedus, he co-produced the 2002 documentary "Only the Strong Survive," which screened at Directors' Fortnight at the Cannes Film Festival.

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