Diane Keaton is among Hollywood’s most universally loved actresses, so why hasn’t she been on a date in more than 30 years?

Veteran Hollywood actress Diane Keaton is ostensibly a woman who walks to the beat of her own drum. In fact, the 73-year-old style connoisseur has largely navigated her life solo. And although she’s dated high-profile actors over the years, she apparently hasn’t been on a date in more than 30 years.

Keaton, who entered the world as Diane Hall on January 5, 1946, is known and loved by many – and it’s easy to see why. But although she’s celebrated as an actress who has won Oscars, Golden Globes and BAFTAs, she wears many other hats, too. Yes, not only is she a director and a producer, but she also dabbles in photography and real estate as well as writing and singing.

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That said, Keaton’s first love growing up was acting. Her career choice came instinctively, apparently, after she was inspired by the flamboyance of a homemakers’ pageant that her mother, Dorothy, had won. And Keaton also developed a love of photography through her mom’s pastime. In fact, in 1980 the actress published a book, Reservations, that showcases images of hotel interiors she’d collected during her travels.

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Meanwhile, Keaton’s father, John Hall – commonly referred to as Jack – was a real estate agent who no doubt inspired another of her hobbies: flipping houses. But the young aspiring actress always seemed drawn to strong, empowered women. Katherine Hepburn, who was well known for portraying such savvy characters, was a particularly big influence on Keaton.

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Keaton would go on to attend Santa Ana High School in California, where she indulged her love of performing through various societies. And when the school put on a production of the Tennessee Williams play A Streetcar Named Desire, Keaton scored the lead role of Blanche DuBois. She graduated from the school in 1964.

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After graduation, Keaton enrolled at first at Santa Ana College before briefly switching to Orange Coast College to concentrate on acting. However, she felt a pull toward the stage and quit after a year to move to New York. She then joined the Actors’ Equity Association and, after learning of another aspiring star called Diane Hall, changed her name to Keaton – which had been her mom’s name before marriage.

As an aside, Keaton sang in clubs – an vocation notably shared by her character in 1977’s Annie Hall. During the day, however, the future star studied at New York’s famous Neighborhood Playhouse, learning an acting method called the Meisner technique. Her first gig was a nine-month run on Broadway in 1968 with a minor part in Hair.

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Then, when Keaton’s time in Hair came to an end, she tried out for Woody Allen’s take on Play It Again, Sam. Interestingly, she nearly didn’t get the part as she was noticeably taller than Allen. And yet not only was her audition successful, but she also received a Tony Award nod for her performance.

What’s more, while starring together on Broadway, Keaton and Allen became close and started dating. But although the pair’s romance lasted only a year, their friendship and working relationship continued. In fact, Keaton would go on to star in no fewer than eight Allen movies, including the screen adaptation of Play It Again, Sam, Annie Hall, Sleeper and Manhattan.

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Keaton’s big-screen debut came in the 1970 comedy Lovers and Other Strangers. It was among the highest-grossing movies of the year and received three Oscar nods, winning the gong for Best Original Song. Plus, the success of the film thrust Keaton into the limelight, and her Hollywood career took off.

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Then in 1972 Keaton starred as Kay Adams, the girlfriend-turned-wife of Al Pacino’s Michael Corleone in The Godfather. And she fed off her behind-the-scenes experience of making the movie to portray the character. You see, the actress described her involvement as being “the woman in a world of men” – much like Kay’s place within a male-dominated crime family.

Apparently, director Francis Ford Coppola had selected Keaton for the role of Kay in The Godfather after seeing her in Lovers and Other Strangers. At this point, the young actress had already earned a reputation for being somewhat eccentric, and she herself had claimed that she was dubbed “the kooky actress” of the movie world. But it was a trait that Coppola wanted conveyed in her role.

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The Godfather is, of course, among the most famous and critically acclaimed movies in history. But although Keaton reprised her role as Kay in The Godfather II in 1974, one of her most prominent movie appearances followed later that decade. Yes, she teamed up once again with her former flame Woody Allen for 1977’s Annie Hall.

It’s fair to say, too, that Annie Hall was a pivotal moment in Keaton’s career. In fact, it’s a movie that she credits with setting her up for all the success and accolades that followed. In July 2019 she explained to InStyle, “Obviously, I owe it all to Annie Hall. That was the beginning.” After all, Keaton was Annie Hall.

You see, it’s often been suggested that the character of Annie Hall was developed around Keaton. Her real second name is Hall, for one thing, while friends call her Annie. Plus, of course, there’s the fact that she and Allen were once romantically involved. And, apparently, Keaton has described the part as an “affable version” of her real-life persona.

In fact, Annie Hall and Keaton are perhaps more alike than many fans may know. In November 2011 the Daily Mail described the character as “semi-articulate, dreamed of being a singer and suffered from insecurity.” Keaton reportedly recognized these qualities in herself, too, so it wasn’t a huge challenge to play her – and that’s perhaps why she was surprised to win a Academy Award for her performance.

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On Oscars night, Keaton turned up to the ceremony showcasing her unique style. Unselfconsciously, she’d thrown together a layered outfit of slacks, two skirts, a white shirt, a blazer and a scarf finished with a pink boutonnière and her hair in an unkempt updo. And the actress’ individuality stood out far enough from the glitzy crowd to gain someone’s attention.

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Yes, Keaton caught the eye of famous womanizer Warren Beatty. When the silver-screen legend called her the day before Christmas 1977, it was as though her childhood dreams had come true. After all, Keaton had reportedly been smitten with the heartthrob since her teenage years when she’d watched him in Splendor in the Grass.

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Keaton and Beatty dated from 1978, with their relationship lasting through the production of the 1981 Russian Civil War epic Reds. In the movie, Keaton stars opposite Beatty as a feminist journalist – a challenging role for which she again received widespread acclaim. The actress bagged an Oscar nomination, for one thing, and extended herself beyond the parts that she’d played for Woody Allen.

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In Keaton’s 2011 memoir, she wrote of her romance with Beatty, “I fell, and I kept falling for a long time.” Ultimately, however, the kooky actress reportedly felt uncomfortable among the actor’s high-class friends, such as Anjelica Huston and Jackie Kennedy. She even found him to be somehow unattainable, and eventually their affair fizzled out.

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Then, through the ’80s, Keaton’s acting career wavered. While she shone in 1982 drama Shoot the Moon, her role in thriller The Little Drummer Girl two years later was ill-suited to her, according to critics. And although 1984’s Mrs. Soffel and 1986’s Crimes of the Heart were better matches with higher acclaim, none achieved the success of her earlier movies.

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In her memoir, Keaton noted, “Without a great man writing and directing for me, I realized I was a mediocre movie star at best.” Given the substantial critical acclaim she had previously received, though, the star was selling herself short. But, nevertheless, a “great man” returned to her life in 1987 after a chance encounter with her former co-star Al Pacino.

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When they had first met on the set of The Godfather, Keaton and Pacino had both been in relationships. Even so, Keaton had allegedly harbored a crush on him for the 15 years since. And in 1987 they began an on-again, off-again affair that lasted through the filming of The Godfather III until a nasty breakup in 1990.

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Keaton was convinced that Pacino was the man she wanted to marry. In fact, she apparently insisted to him that they should and so issued an ultimatum.Yet Pacino seemingly didn’t return the sentiment and instead stated that the idea was one that he’d never entertained. Then, two months after Keaton’s dad passed away, Pacino walked out. She was broken.

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From a young age, Keaton had longed to marry one day. In a May 2013 interview with The Daily Telegraph, she recalled, “I remember watching [actress] Myrna Loy being interviewed, and somebody said, ‘It’s too bad you’re not married anymore.’ And she said, ‘I don’t want to be married anymore – not at all.’”

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And Loy’s attitude had shocked Keaton. She continued, “I remember thinking, ‘How sad. How could anybody come to that? I was in the prime of my life. You’re biologically driven in some way; you can’t help it, you’re an animal. So I looked at her and thought, ‘That will never happen to me.’” Only it did.

Clearly, Keaton’s high-profile romances go hand in hand with her illustrious acting career. But while the star’s work on screen continued through the ’90s, ’00s and ’10s, the same can’t be said of her love life. In fact, in July 2019 she made a very surprising admission.

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Keaton told InStyle magazine, “I haven’t been on a date in, I would say, 35 years. No dates.” Basic arithmetic, then, would suggest that the actress’ departure from dating came around the time of her relationship with Al Pacino. There is, however, a very simple reason that the Hollywood veteran hasn’t been in the dating game for so long.

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You see, Keaton confessed to InStyle that she never gets asked out. She joked, “Never. All right?” And it seems as though this is the very reason that the veteran actress never married, either. Yes, while she once dated some of Hollywood’s leading men, they have been notable by their absence from her recent private life.

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Plus, back in April 2013 Keaton had confessed to Ellen DeGeneres, “I’d like to get married. What happened was nobody ever asked me.” But forget any ideas of a lonely spinster. Keaton has kept herself far too busy with work, hobbies and family in her later years to subscribe to such an uncouth cliché.

“I’m an old maid!” she declared to The Daily Telegraph, tongue firmly in cheek and roaring with laughter. “That concept is such nonsense – the idea that if you never marry you’re destroyed. I can’t imagine marrying now; that’s not happening.” Keaton is, of course, nothing if not unconventional, describing herself as an “oddball.”

Keaton admitted to People in May 2019, “I think I’m strange. I’m 73, and I think I’m the only one in my generation – and maybe before – who has been a single woman all her life.” She even wonders if she lacks a certain “nurturing” characteristic that would make a marriage successful.

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Indeed, Keaton talks at length in her memoir, Then Again, about the insecurities and five-year battle with bulimia that blighted her relationship with Allen. Beatty, on the other hand, was able to take what therapists called “anxiety neurosis” and use it to her advantage. Keaton said, “Under his gaze, I suddenly became the most captivating person in the world.”

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Apparently, Beatty’s belief was that Keaton could achieve anything that she set her mind to. It was an assessment of her character that she ran with to expand her repertoire. As well as a revered actress, Keaton is now a director, a producer, a writer, a photographer, a fashion icon and a singer. And in 1996 she took on arguably her most challenging role yet.

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You see, while Keaton may never have married, motherhood was something that she was determined to not miss out on. So, at 50 years old, the actress adopted daughter Dexter, with son Duke following in 2001. But although Keaton harbors mixed feelings over the lack of a father figure in her kids’ lives, she has no regrets about not wedding.

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“I don’t think it would have been a good idea for me to have married, and I’m really glad I didn’t,” Keaton told People. “I’m sure they’re happy about it too.” Indeed, by all appearances, the actress is refreshingly unconventional with a personality that’s at odds with more typically aloof Hollywood legends. And nowhere is that more evident than on Instagram.

Yes, Keaton’s Instagram page is a window into her quirky soul. In May 2019 she posted a video in which she’s wearing a tweed blazer with a wide belt that’s cinching her waist, black slacks and heavy boots. In the clip, she asks her viewers, “Which hat do you think I should wear?” Referring to the half dozen balanced on her head, she adds, “Should I wear them all?”

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Impressively, Keaton has starred in 58 movies to date. In 2017 the American Film Institute honored her with their 45th Life Achievement Award. And all three of her most famous ex-lovers, including Pacino – whose path Keaton has apparently rarely crossed since their 1990 breakup – attended the ceremony. The Godfather star declared from the stage, “You’re a great artist. I love you forever.”

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However, one ex has remained in Keaton’s life for around 50 years. She wrote in her memoir, “I miss Woody. He’d cringe if he knew how much I care about him, but I’m smart enough not to broach the subject.” And she added, “What am I supposed to do? I still love him.”

Perhaps Keaton’s humorous Instagram post could stand as a metaphor for her single life. She does, after all, get to wear all of the hats all the time. But nevertheless, Allen speaks of his old flame fondly. At her AFI Life Achievement ceremony, the director said, “Diane is the most unique person I’ve ever known. That could be interpreted as weirdness, but she’s truly one of a kind.”