Diane Keaton's Relationships: The Men She Never Married

From her creative bond with Woody Allen to her passionate romance with Al Pacino and her whirlwind affair with Warren Beatty, Diane Keaton's relationships were as captivating as the roles that made her a legend.

Diane Keaton may have never walked down the aisle, but her love life was anything but ordinary. The Oscar-winning actress shared deep connections with some of Hollywood's most celebrated men — each relationship shaping a different chapter of her storied life.

Al Pacino: The One Who Got Away

Keaton's attraction to Al Pacino began while they worked together on "The Godfather" in 1971. She noted that she "had a crush on him." She later developed strong feelings for him, drawn to his charm, humor, and constant stream of conversation.

To her, he had the air of a lost orphan — a brilliant, gorgeous, and yet unpredictable man who fascinated her as much as he frustrated her. She found him irresistibly handsome and grew deeply attached during their time together.

However, when Pacino refused to take the next step toward marriage, she gave him an ultimatum that ultimately ended their relationship. In hindsight, she admitted, "I worked hard on that one. I went about it in not a perfect way."

Keaton reflected further that Pacino was the one who truly slipped away. She hadn't been expecting a grand proposal; she simply hoped marriage would happen naturally between them. "But that never happened, and that is a blessing for both of us. It would have been a nightmare for him," she said.

Speaking about that chapter of her life, she grew visibly emotional, acknowledging that both of them were too unconventional to make it work. In Keaton's view, Pacino needed someone who could care for him, while she longed for a man who could do the same for her.

"It was just very important that we left each other alone, said goodbye. But it wasn’t my choice," she added.

Pacino has also shared warm memories of Keaton over the years. During the "AFI Life Achievement Award: A Tribute to Diane Keaton," he reflected on their enduring bond, saying he felt as though he had known her all his life and that they shared countless memories.

The two first crossed paths in East Harlem at a small restaurant called Patsy's, where the close-knit cast of "The Godfather" gathered, and it was there that Keaton also met Marlon Brando for the first time.

Al Pacino also recounted a moment when he was preparing for an interview — something that always made him uneasy. Keaton, ever the encourager, had offered him advice as he was heading out the door. As he left, she called after him, telling him he'd be fine, but whatever happened, he must not say he was an artist.

It was advice he remembered hilariously and fondly, noting it was good counsel. He concluded with a heartfelt message, "But I have to say now, dare I say it, forgive me. You are an artist, Diane. You are a great artist. I remember it and I love it and I love you forever."

Diane Keaton and Woody Allen's Unshakable Bond On and Off Screen

Keaton and Allen's professional and personal connection became one of Hollywood's most fascinating creative partnerships, producing some of the most memorable films of the 1970s. "Annie Hall," a film so intimate and authentic that audiences couldn't help but wonder how much of it reflected their own real-life romance.

The story follows a successful comedian who meets a quirky, awkward singer-actress on a Manhattan tennis court.

Her character is shy, prone to saying the wrong things, drives a Volkswagen through the city with little restraint, and relies on marijuana to enjoy intimacy. She also comes from an antisemitic family in Chippewa Falls, Wisconsin, and battles enormous spiders in her bathtub.

After parting ways with the comedian, she has an affair with a Hollywood musician played by Paul Simon. When asked about how much of the movie reflected her real life, Keaton clarified, "It's not true, but there are elements of truth in it."

She added that it drew inspiration from genuine parts of her and Allen's shared experiences. For instance, her real last name was indeed Hall, just like her character's, and she did own a Volkswagen. However, she described herself as a slow, cautious driver rather than a reckless one.

While she admitted to being easily flustered when meeting men, she said she didn't smoke marijuana, except during her time in "Hair." "But it makes me a little nervous, and I feel nervous enough without it. I like a glass of wine, which makes me more relaxed," she shared.

Keaton also noted that her parents were nothing like those depicted in the film. They were from Balboa Island, California, and were not at all similar in temperament to her character's fictional family.

She had also never encountered spiders in her bathtub — though she did recall finding roaches — and had certainly never had an affair with a rock musician.

Interestingly, she and Allen hadn't met on a tennis court as in the movie, but during her audition for his play "Play It Again, Sam," marking the beginning of both their professional collaboration and personal connection.

She admitted, "I had a huge crush on Woody right from the moment I saw him." Their height difference became a lighthearted detail during the casting process — with Allen standing at 5'7".

The two were asked to stand head-to-head to compare. Keaton remembered that she ultimately landed the role because she wasn't taller than him. She later shared that she found Allen "hilarious" during filming, a trait that sparked their personal rapport.

Looking back, Keaton reflected that she still couldn't quite pinpoint how their friendship began, noting that becoming close to Allen was rare, given how private he has always been.

Keaton spoke fondly of Allen, describing him as one of the strongest people she had ever known. "He's made of steel. And talk about a work ethic – he's one of the people that really did teach me that you have to work hard. But he wanted to. He's the most disciplined person I've known, with the exception of my dad," she gushed.

She observed that Allen's discipline never wavered, unlike her father's, which faded after retirement. Allen, she noted, would likely keep practicing his clarinet, touring with his band, and directing one film a year for as long as he could.

"Who in the history of movies has done that? He's 78, he makes a movie a year and he has total control. How is that possible?" she questioned.

Keaton also once recalled a day she shared with Woody Allen in New York City, riding together in a taxi along Madison Avenue. Their lighthearted exchange, prompted by traffic and a passing comment from the driver, was one of many moments that captured the humor and ease that defined their friendship.

"I've known Woody all my adult life, and clearly I love him. He's hilarious and brilliant. What can I say? There are few people you get to know that well in life," she said.

Keaton added, "That’s why I feel privileged to be in that rarified world of people who're old news. I've been around forever, I'm someone he's known forever. He can't get rid of me. I'll always be his friend, and that's never going to go away."

Professionally, she admired his focus, noting that no amount of public scrutiny could distract him from his work. She viewed his consistency as a strength shared by great filmmakers, citing how dedication often carries artists through life's challenges.

When Keaton returned to work with "Allen on Manhattan Murder Mystery" after a long hiatus, she was reminded of his extraordinary skill as a director. His approach, she observed, could be deceptively simple — often making actors feel as though they weren't being directed at all — yet the results spoke for themselves.

"People are excited to work with him because obviously he's one of the greatest filmmakers America's ever produced. Everybody wants to be in a quality product, and they trust him, so he's done very well with actors," Keaton acknowledged.

She also admitted that working with him wasn't always easy. The process demanded precision and could be nerve-racking, especially after years apart.

Still, once filming began, the familiar rhythm between them quickly returned. For Keaton, the experience was like revisiting family — challenging at times, but deeply comforting and impossible to replace.

Warren Beatty: From a Distant Admiration to a Complex Connection

When speaking about Warren Beatty, Keaton recalled being captivated by him long before they ever met. Watching him in "Splendor in the Grass" in 1961, she realized that she had a "teen crush" on him.

Keaton found him magnetic, strikingly handsome, effortlessly charming, and every bit the movie star. Later, his work in "Bonnie and Clyde" only reinforced her admiration, not just for his on-screen charisma but for his extraordinary talent behind the camera as a director and producer.

Eventually, Keaton met Beatty in the early 1970s, around the time her career was beginning to take off. She recalled being at the Beverly Wilshire Hotel, where she spotted him at the lobby from a bookstore window.

"I thought, My god, he's so beautiful. It was like there was a light. He looked at me for a second, and then [his eyes] passed me by. I thought, I’ll never know him. He’ll never be somebody in my life," she narrated.

Their relationship, which began a few years after the success of "Heaven Can Wait," was marked by passion and complexity. Those close to the couple described it as intense and often volatile.

According to Jeremy Pikser, whom Beatty hired as a research consultant, "Warren was always trying to please Diane. Which was not easy. Which is why he wanted to do it so much. It’s no fun for him if it’s easy. He really likes women who kick his [expletive]. He always moaned about it, but I think it’s what drew him to her. She was very difficult."

Pikser added, "He bought her a pair of handcuffs, as either a Christmas or a birthday gift. I took that as an ironic comment on her feeling that he wanted to constrain her. Or maybe they were just into that!"

Beatty later dismissed the suggestion that the handcuffs had any risqué meaning, explaining that the idea of using them in that way amused him. He also emphasized, "And there would be about as much chance of Diane Keaton being into that kind of stuff as there would be of her becoming interested in skydiving."

Keaton considered Beatty one of Hollywood's most multifaceted figures. She noted, "He is curious about everyone. He is so seductive in that regard. He makes you feel like you are the only one, the person that matters; that you are just absolutely fascinating, you know?” (Laughing). And it’s with everyone, across the board. He just has this presence."

Beatty also once reflected on how fame had allowed him to meet remarkable women — not just those known for their beauty, but for their intelligence, talent, and character. Among those he spoke most fondly of was Keaton, with whom he developed a close relationship while working together on the 1981 film "Reds."

"I love her. She’s a combination of integrity and humor and intelligence and fairness and, did I say beauty? A brilliant comedic sense," he enthused. Keaton also shared that starring in "Reds" was one of the most meaningful experiences of her career.

She expressed gratitude to Beatty for allowing her to explore a deep and transformative kind of love through her character, saying the experience elevated her life from ordinary to extraordinary.

For her, working alongside him — with Beatty directing and her performing — created moments she would never forget.

Each of these men Keaton dated brought out a different side of her — Pacino stirred her heart, Allen shaped her artistry, and Beatty awakened her sense of daring.