We may receive a commission on purchases made from links.

During her golden heyday, Diane Keaton had her pick of Hollywood’s hottest and hunkiest Hollywood bachelors — oh, and Woody Allen. She made the most of it, racking up a dating list that reads like a who’s who in Hollywood. Still, the actor never settled on a Mr. Right, preferring instead to work her way through a long list of Mr. Right Nows.

Despite enjoying rumored steamy trysts with such gorgeousness as Keanu Reeves, Keaton never got married. She explained in a 2021 Interview magazine Q&A that she chose the single life because she never wanted to compromise her freedom, citing her mom’s shattered hopes as motivation. “I feel like my mother chose family over her dreams,” Keaton said. “She was the best mother, but I think she’s the reason why I didn’t get married. I didn’t want to give up my independence.” Besides, she quipped, nobody ever bothered to ask her.

One leading man who wasn’t one of Keaton’s A-list liaisons is Liam Neeson. However, that didn’t stop her from flirting with (or more likely teasing) him when he asked in the Interview Q&A if he was her best on-screen lover. “Yes, of course. That goes without saying,” Keaton replied. “And you’re easy on the eyes. I don’t think I’ve seen you in 30 years, but yes, you’re the best on-screen lover ever. No hesitation on that.” Well, Neeson didn’t make the cut, but plenty of other fortunate fellows did — we’re checking out some of them.

Diane Keaton’s first high-profile partner was Woody Allen. The couple collaborated on eight movies, including “Annie Hall,” which won Keaton a Best Actress Oscar in 1978. Keaton and Allen dated for three years during the ’70s, but first met in the late sixties when Keaton was an up-and-coming actor fresh off the Broadway show “Hair.” Allen was an established director and actor looking for a female lead to play his love interest in the stage version of “Play it Again, Sam.” She landed the role and went on to revive it in the film version.

Keaton admitted to the New Yorker in December 1996 that she immediately fell hard for Allen, who, by all accounts, was quite the ladies’ man. “He could always get the girls, you know,” Keaton said. “Girls have always liked him and had crushes on him because he’s so funny and talented.” In a May 2013 interview with The Telegraph, Keaton hinted that Allen dumped her after struggling with her rollercoaster emotions.

Still, they remained close, and Keaton was one of the few who defended Allen when his daughter, Dylan Farrow, accused him of molesting her as a child. Meanwhile, Allen claimed to be heartbroken over Keaton’s death, all while managing to make it about him. “He is extremely distraught and surprised and upset,” a source told People on October 11. “It makes him think of his own mortality.”

Diane Keaton met Al Pacino on the “The Godfather” set in 1971. It was love at first sight for Keaton. “I was mad for him. Charming, hilarious, a nonstop talker,” she admitted to People in 2017. “There was an aspect of him that was like a lost orphan, like this kind of crazy idiot savant. And oh, gorgeous!”

However, Pacino was a slow burn. He wasn’t willing to dive right in, and they didn’t start dating until long after the cameras stopped rolling. But when they did start hooking up, they didn’t stop for 15 years — albeit with plenty of breakup respites along the way. Keaton was so crazy about her co-star that she was even willing to break her sacred no-marriage vow, tearing up the rule book and throwing it out the window.

However, Keaton and Pacino couldn’t make it work, and everything came to a screeching halt after she issued him an ultimatum: Put a ring on it or go on, go, walk out the door. Pacino chose the latter, and just like that, they were done. They remained close friends and retained a strong bond, though. “That has a special meaning,” Keaton said on “The Ellen DeGeneres Show” when a photo of Pacino popped up during a “Who would you rather?” segment in December 2017. “He once enjoyed being around me. But only on occasion. Not often. But he once, you know.”

If you were a woman in Hollywood during the ’70s and ’80 with your own teeth and a pulse, there’s a very good chance you might have hooked up with the OG Lusty Lothario, Warren Beatty. Diane Keaton did, and the couple put their relationship out there — well, kind of — for all to see. They also shared the screen together in the 1981 movie “Reds,” which Beatty wrote, produced, directed, and acted in. It was a work of fiction, but at times it felt unnervingly factual for Keaton. “There’s a scene where we’re fighting that felt really real,” she once told People.

Beatty was a notorious womanizer who cycled through girlfriends like underwear. However, Keaton wasn’t just another notch on Beatty’s bedpost. Far from it, in fact. The two actors became a “thing” — and a very passionate one by all accounts — for five years.

Keaton and Beatty ultimately didn’t work out. But she remained his biggest champion and cheerleader after things ended. “He was, I mean, to die for. A Dream. … Not only was he beautiful, gorgeous and sexy and captivating and mysterious, and a great movie star, but he was also an unbelievable producer and director,” Keaton told Variety in November 2016. Beatty was equally generous with the praise. “I love her,” he told People that same month. “She’s a combination of integrity and humor and intelligence and fairness and, did I say beauty? A brilliant comedic sense.”

There’s no disputing the sizzling hot chemistry between Diane Keaton and Keanu Reeves in the 2003 Nora Ephron romcom “Something’s Gotta Give” — even if she did make the inexplicable decision to dump Reeves in favor of Jack Nicholson. Things were so steamy between the two that it was rumored the passion spilled over into real life, too, resulting in Keaton and Reeves embarking on a secret relationship. Adding yet further to the intrigue, there was also gossip that he dumped his girlfriend, Lynn Collins, to be with Keaton.

They’ve both stayed schtum on the subject aside from the occasional quip by Keaton. “We were [in a movie] and he also loved me,” she said on “The Ellen DeGeneres Show” in December 2017. “He loved me a lot. Not just a little tiny bit … it expanded. His love grew with time.”

Meanwhile, their chemistry was out there for all to see again in February 2020 when they reunited to announce the Oscar nominees for best original screenplay. “Hello, Diane,” Reeves said. “Hello there, Keanu,” she replied. “It’s been a long time since you and I made that movie, that movie ‘Something’s gotta give.’ Remember me in it?” Reeves certainly did, commenting on how “amazing” she was to work with. “We had some really … Well, let’s be frank, it was really good times,” Keaton said.