Diane Keaton Once Confessed She Is ‘Glad’ She Never Married – Her Dating History in 30 Pics

Diane Keaton’s love life was anything but typical, ranging from an emotional fallout with Al Pacino to a humorous spark with Keanu Reeves and even an embarrassing encounter with tech royalty Steve Jobs inside his mansion.

Famous for her skill and sense of style, as well as her fiercely independent outlook on life and love, beloved actress Diane Keaton was in the public eye for more than 50 years.

Keaton never got married in her 79 years of life. She frequently thought frankly on her personal relationships and talked honestly about why marriage never appealed to her.

The Reason Diane Keaton Didn’t Get Married
As Keaton put it frankly in a 2019 interview with People, “I don’t think it would have been a good idea for me to have married, and I’m really glad I didn’t, and I’m sure they’re happy about it, too.”

She never felt the need to become a wife and didn’t think of herself as inherently nurturing. She was happy to be alone and openly referred to herself as odd, even in her old years.

She admitted in a 2023 interview that she hadn’t dated in roughly 15 years, joking that perhaps her individuality was a contributing factor.

Despite having famous people in her romantic life, Keaton consistently maintained her single status. She frequently claimed that she was better off as a result, and she ultimately accepted living her life as she saw fit.

The One Who Got Away: Al Pacino
Keaton’s relationship with Al Pacino was her most intense and agonizing. Though their relationship didn’t become intimate until later, they first crossed paths while filming “The Godfather” in the early 1970s.

The 1980s were filled with its intermittent romance. Pacino’s charm, wit, and mystery captivated Keaton. He didn’t desire marriage, but she did.

She issued him an ultimatum in 1990. He declined. That was the end. “Then Again,” her 2011 book, states that “he never had any intention of marrying me.”

“Marry me,” she once begged him, “or at least commit to the possibility.” “I wanted more, lots more,” she admitted. A ton. As much as I wanted him, I wanted him to want me back.

The last rupture occurred soon after her father passed away, when Pacino told her he wanted to leave during a therapy session. Years later, Keaton claimed that she once became so upset that she puked after seeing him on TV out of the blue.

She became emotionally withdrawn when their relationship ended, even changing her wardrobe to feel more defensive. Time, however, provided her some perspective.

“Even a proposal wasn’t something I wanted. I simply believed that perhaps one day he would wed me,” she claimed. ‘Don’t even propose, let’s just do it,’ I thought. However, it never occurred, which is fortunate for us both. For him, that would have been a nightmare.

She went on to say, “We’re quite different; I needed a man who would look after me, and he wanted a woman who would look after him. Simply put, it was crucial that we say our goodbyes and leave each other alone. However, I had no say in the matter.

Woody Allen: Faithfulness in Real Life and Cinema
While filming “Play It Again, Sam” (1972), “Love and Death” (1975), and the Oscar-winning “Annie Hall” (1977), Keaton dated Woody Allen in the early 1970s, one of her first and most well-known relationships.

Keaton told The New York Times in 1977 that “Annie Hall” wasn’t based on their real-life romance, despite the fact that many people thought it was, even though there were “elements of truth in it.”

Their professional and personal relationship remained strong even after their romance chapter ended.

Keaton later served as one of Allen’s few public defenders when accusations of sexual abuse against his daughter Dylan Farrow, which had been made in 1992, came to light again.

“Woody Allen is my friend and I continue to believe him,” Keaton tweeted in 2018. She then urged viewers to view a “60 Minutes” interview from 1992 in which Allen refuted the accusations.

Warren Beatty: Intelligent and Dreamy
Working on “Reds” (1981), when she portrayed journalist Louise Bryant, both his character and, for a brief moment, his real-life love interest, Keaton and Warren Beatty fell in love.

They stayed close friends even though their romance ended in the 1980s. A “brilliant character” is what Keaton once described Beatty as in an interview with People.

She thought back on their relationship with Variety in 2016, remembering how amazed she was as a teenager to witness him in “Splendor in the Grass.”

She exclaimed, “Come on! I mean, he was absolutely amazing. A dream. ‘Bonnie and Clyde?’ I mean Hurry up. And in addition to his beauty, he was an amazing director and producer.

Even when the affair dissolved, she continued to admire Beatty.

Edward Ruscha: A Silent Friend
Keaton’s romance with artist Edward Ruscha was one of the most private periods of her life. For a while, they were romantically involved, although not many specifics were ever revealed to the public.

Despite dating one of Hollywood’s most well-known ladies, Ruscha, who is renowned for being quiet and media-averse, maintained a low profile.

Steve Jobs: An Odd High-Rise Meeting
Steve Jobs, a co-founder of Apple, unexpectedly invited Keaton to meet him after “Annie Hall” made her a household name. Keaton occupied the San Remo building in New York during the time. Jobs had recently purchased the upper levels.

She consented to come to his flat, but things didn’t work out. Keaton claims that Jobs talked about computers and technology the entire time he was there. They never saw one another again, never shared a kiss, and never went on a date.

Given that her memoir was eventually written on the exact kind of computer that Jobs had been fixated on that evening, she smiled about the experience years later.

Nicholson, Jack
In her thirties, Keaton first met Jack Nicholson, with whom she later costarred in “Something’s Gotta Give.” He never returned the long-standing crush she had on him.

“I had no intention of becoming his friend. I desired a kiss from him. “It never happened,” she once acknowledged.

In spite of this, the two grew close. He even received love letters from Keaton. In other instances, she said, “Looking at you for as long as I have has made it easy for me to come to the conclusion that your face is the best face I’ve ever seen.”

Although their on-screen chemistry generated a lot of fan speculation, they remained faithful and platonic in real life.

Keanu Reeves: vivacious and endearing

Keaton costarred with Keanu Reeves in the 2003 film “Something’s Gotta Give.” She portrayed Erica Barry, a playwright who develops feelings for the younger doctor played by Reeves.

Although neither of them ever acknowledged it, their on-screen chemistry generated rumors of a real-life romance.

“Keanu Reeves was in the same movie… and he also loved me,” Keaton quipped years later. It wasn’t a tiny bit; he loved me deeply. It grew. Over time, his affection deepened. I like him, then. I’ll take Keanu.

The two reconnected at the 92nd Academy Awards in 2020 and engaged in a playful, flirtatious conversation. They got along well, but there was no proof that they were more than friends.

Richard Gere: An Unsticky Crush
Richard Gere and Keaton had a relationship that began with their 1977 movie “Looking for Mr. Goodbar.” Years later, they collaborated once more, but romance never blossomed.

“I had a crush on him, but he didn’t cotton to me at all,” Keaton said, looking back on their early years. In the film, he was expected to care about me, but he didn’t want to. But he’s fantastic. He was excellent.