Diane Keaton Once Confessed She Is 'Glad' She Never Married — Her Dating History in 30 Pics

From an emotional fallout with Al Pacino to a cheeky spark with Keanu Reeves and even an awkward brush with tech royalty Steve Jobs inside his penthouse, Diane Keaton's love life was anything but ordinary.

Beloved actress Diane Keaton spent more than five decades in the spotlight, known not only for her talent and style but also for her fiercely independent approach to life and love.

In all 79 years of her life, Keaton never married. She often spoke candidly about why marriage never appealed to her and reflected openly on her romantic relationships.

Why Diane Keaton Never Married

In a 2019 interview with People, Keaton stated bluntly, "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 didn't consider herself naturally nurturing and never felt the urge to become a wife. Even in her later years, she proudly called herself eccentric and content on her own.

In a 2023 interview, she revealed she hadn't dated in about 15 years, quipping that maybe her uniqueness had something to do with it.

Though her love life included major names, Keaton always stood by her decision to remain single. She often said she was better off for it — and in the end, she fully embraced a life lived on her own terms.

1. Al Pacino: The One Who Got Away

Keaton's most powerful and painful romance was with Al Pacino. They first met filming "The Godfather" in the early 1970s, though their relationship didn't turn romantic until later.

Their on-again, off-again love story stretched through the 1980s. Keaton was enamored with Pacino's charm, wit, and mystery. But she wanted marriage; he didn't.

In 1990, she gave him an ultimatum. He refused. It ended for good. In her 2011 memoir "Then Again," she wrote, "He never had any intention of marrying me."

She once pleaded with him, "Marry me, or at least commit to the possibility." She confessed, "I wanted more, lots more. Tons. I wanted him to want me as much as I wanted him."

The final break came shortly after her father's death, when, during a therapy session, Pacino told her he wanted out. Years later, Keaton said seeing him on TV unexpectedly once left her so distressed she vomited.

The end of their relationship led her to close herself off emotionally, even altering how she dressed to feel more guarded. Still, time gave her perspective.

"I didn't even want him to propose. I just thought maybe he would marry me, eventually," she recalled. "I thought, 'don't even propose — let's just do it.' But that never happened, and that is a blessing for both of us. It would have been a nightmare for him."

She added, "We're very eccentric; he needed a woman that was going to take care of him, I needed a man who would take care of me … It was just very important that we left each other alone, said goodbye. But it wasn't my choice."

2. Woody Allen: Loyalty in Life and Film

One of Keaton's earliest and most public relationships was with Woody Allen, whom she dated in the early 1970s while filming "Play It Again, Sam" (1972), "Love and Death" (1975), and the Oscar-winning "Annie Hall" (1977).

Though many believed "Annie Hall" was based on their real-life romance, Keaton told The New York Times in 1977 that it wasn't — though there were "elements of truth in it."

Their romantic chapter ended, but their professional and personal bond never broke.

In later years, Keaton was one of Allen's few public defenders during the resurfacing of sexual abuse allegations involving his daughter, Dylan Farrow — allegations first raised in 1992.

In 2018, Keaton tweeted, "Woody Allen is my friend and I continue to believe him." She then encouraged people to watch a 1992 "60 Minutes" interview in which Allen denied the allegations.

3. Warren Beatty: Dreamy and Brilliant

Keaton and Warren Beatty fell for each other while working on "Reds" (1981), where she played journalist Louise Bryant — both his character's and, briefly, his real-life love.

Their relationship didn't last past the 1980s, but they remained close friends. Keaton once called Beatty a "brilliant character" in an interview with People.

In 2016, she reflected on their history with Variety, recalling her teenage awe at seeing him in "Splendor in the Grass."

She gushed, "I mean, come on! He was, I mean, to die for. A Dream. I mean, ‘Bonnie and Clyde?’ Come on. And not only was he beautiful... but he was also an unbelievable producer and director."

Her admiration for Beatty never wavered, even after romance faded.

4. Edward Ruscha: The Quiet Companion

One of the most private chapters of Keaton's love life was her relationship with artist Edward Ruscha. They were linked romantically for a time, though few details were ever made public.

Ruscha — famously low-key and media-averse — kept a low profile, even while dating one of Hollywood's most recognized women.

5. Steve Jobs: A Strange High-Rise Encounter

After "Annie Hall" catapulted her to superstardom, Keaton received a surprising invitation: Apple co-founder Steve Jobs wanted to meet her. At the time, Keaton lived in the San Remo building in New York. Jobs had just bought the top floors.

She agreed to visit his apartment — but the meeting didn't go as expected. According to Keaton, Jobs spent the entire visit discussing technology and computers. They never kissed, never went on a date, never saw each other again.

Years later, she laughed about the encounter — especially since her memoir was eventually written on the very type of computer Jobs had been obsessing over that night.

6. Jack Nicholson

Keaton met Jack Nicholson in her 30s and later starred opposite him in "Something's Gotta Give." She harbored a long-standing crush — one he never returned.

"I didn't want to be his friend. I wanted him to kiss me. It didn't happen," she once admitted.

Despite that, the two became deep friends. Keaton even wrote him love letters. In one, she confessed, "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."

Their on-screen chemistry sparked endless fan speculation, but in real life, they stayed platonic — and loyal.

7. Keanu Reeves: Flirty and Forever Charming

In 2003, Keaton starred opposite Keanu Reeves in "Something's Gotta Give." She played Erica Barry, a playwright who falls for Reeves' much younger doctor character.

Their on-screen chemistry led to buzz about a real-life romance — though neither ever confirmed it.

Years later, Keaton joked, "Keanu Reeves was in the same movie… and he also loved me. He loved me a lot — not just a little tiny bit. It expanded. His love grew with time. So I like him. I'll take Keanu."

In 2020, the pair reunited at the 92nd Academy Awards, sharing a lighthearted, flirty exchange. Despite their rapport, there was no confirmation of anything beyond friendship.

8. Richard Gere: A Crush That Didn't Stick

Keaton's connection with Richard Gere dated back to their 1977 film "Looking for Mr. Goodbar." They worked together again years later — but romance never sparked.

Reflecting on their early years, Keaton admitted, "I had a crush on him, but he didn't cotton to me at all. He was supposed to care about me in the movie, but he didn't want it… He's great, though. He was great."

Like many of her relationships, it was one-sided but warm, and she recounted it with her usual self-deprecating charm.