Warren Beatty and Annette Bening's Relationship Timeline: From Hollywood Costars to Proud Parents

Warren Beatty and Annette Bening have one of the longest marriages in Hollywood.

Though the iconic leading man was famous for his playboy persona before marrying Bening in 1992, Beatty knew he had found the right person for him when they crossed paths.

The actor and the actress connected before filming Bugsy, the 1991 crime drama, and have been inseparable ever since. What started as a business lunch to discuss the movie quickly turned into a relationship and then decades of marriage.

Beatty and Bening wed two months after welcoming their first child, Stephen, in 1992. The couple went on to have three more children: Ben in 1994, Isabel in 1997 and Ella in 2000.

Bening has opened up about how her relationship with Beatty has stayed exciting over the years. "I think in some ways we're very different, some ways we're alike," Bening said on the Today show in 2016. "But the differences, I think, help us and there's some fire there. We want the same things."

Beatty echoed this sentiment when talking to PEOPLE in 2016. “Every day she surprises me,” he said when asked about the secret to their lasting relationship.

From their Bugsy days to raising four children, here's everything to know about Warren Beatty and Annette Bening's relationship.

November 1990: Warren Beatty invites Annette Bening to lunch

When Beatty was casting Bugsy, he thought of Bening for the role of Virginia Hill, the girlfriend of the titular gangster. Beatty called the actress to chat about the part and asked her out to lunch. After the two dined and walked together, it dawned on Beatty that he had found the film's leading lady and his future wife.

When he returned to his office after lunch, he called director Barry Levinson and declared, "I love her, and I'm going to marry her."

Still, he was aware that he was making a big lifestyle change by settling down. He later recalled to the New York Post, "It took about 10 minutes [to fall in love with her]. Maybe five. I was so elated to meet her, and yet at the same time, I began to mourn the passing of a way of life."

January 8, 1992: Warren Beatty and Annette Bening welcome their first baby

Less than a month after the release of Bugsy, the couple became parents. Their first child, Stephen Ira Beatty, was born on Jan. 8, 1992.

Ahead of the birth, Warren faxed a message to PEOPLE that read, "As you might have guessed, I'm still avoiding talking to the press about personal things, but I can tell you I couldn't be happier about having a baby with Annette."

March 3, 1992: Warren Beatty and Annette Bening get married

When Beatty and Bening wed in a private ceremony, only their newborn experienced the special moment with them.

The Reds star revealed that while some were shocked that he settled down, he wasn't.

"It didn't really surprise me. ... I had no doubt when I met Annette that it was time to get married," he said on Today in 2016, adding that he "wasn’t trying to avoid marriage" but divorce.

March 30, 1992: Warren Beatty and Annette Bening make their red carpet debut as a married couple

The couple walked the red carpet at the 64th Academy Awards only weeks after marrying. Beatty was up for Best Actor and Best Picture for Bugsy, two of the film's 10 total nominations.

Bening stepped onstage to present the award for Best Art Direction, which Bugsy nabbed along with Best Costume Design.

August 23, 1994: Warren Beatty and Annette Bening welcome their second baby

The pair's second child, Benjamin Beatty, was born in August 1994. Benjamin has pursued an acting career of his own and was featured in the 2016 period comedy Hail, Caesar! and the 2018 science fiction film UFO.

October 1994: Warren Beatty says he knew Annette Bening was the one

While speaking to Robert Ebert in 1994, Beatty stated that marrying Bening was an easy choice.

"When you're older and you meet somebody, the decision-making process is a lot shorter. ... And that happened here and I listened to it," he said. "And by listening to it, it enabled me not to question it too much ... and I never did."

January 11, 1997: Warren Beatty and Annette Bening's third baby is born

In January 1997, the couple welcomed their third child, Isabel Beatty. She has performed in a number of short films, including Murder Tag (2018), Baggage (2019) and Admitted (2021).

January 8, 1999: Annette Bening says she and Warren Beatty don't have plans to work together again

In 1999, Bening addressed their joint project, the 1995 romantic drama Love Affair, in which she and Beatty starred opposite each other as the leads.

After it didn't take off at the box office, the actress admitted they didn't plan on working together again following the film's reception. She also acknowledged how their relationship may have affected public opinion.

"I think if you're the woman who happens to be married to Warren Beatty you're on a hiding to nothing in almost every situation," she told The Mirror. "There is a long, long queue of people waiting to get at you."

She continued, "I have had to put up with that for years and don't expect any change. If you work together it's like standing there with a sign saying, 'Come on and throw something.' "

April 8, 2000: Warren Beatty and Annette Bening's fourth baby is born

In April 2000, the couple welcomed their fourth and youngest child, Ella Beatty.

In 2022, Deadline announced that she would act in the second season of Ryan Murphy's anthology series, Feud: Capote vs. The Swans, set to premiere on Jan. 31, 2024.

December 31, 2011: Annette Bening says her age gap with Warren Beatty has never been an issue

Beatty and Bening have a 21-year age gap, but the actress revealed it was never a problem.

She told Express in 2011, "I had never been attracted to younger guys. I had, from my late teens, always liked men who were older than me."

May 2016: Warren Beatty details life before and after starting a family

After a 15-year hiatus from acting, Beatty returned to the big screen with Rules Don't Apply in 2016.

He told PEOPLE that his long absence was due to enjoying his family life. "I have four children and any one of them is more interesting than any 12 movies I've done," he said. "I had my life before them and my life since them."

November 2, 2016: Warren Beatty says "respect" is key to his long marriage with Annette Bening

As Beatty and Bening's marriage progressed, the public became increasingly interested in their secret to a long-lasting partnership. While speaking on the Today show in 2016, Beatty said that his marriage hinges on one word: "respect."

Bening had her own interview on the Today show a month later, where she was asked the same question and answered with her husband's response in mind.

She said, "I like 'respect' ... But also, we have four children and they're incredible human beings. Having that shared purpose also is part of it."

November 16, 2016: Warren Beatty says he is happy about the path he took to marriage

Beatty married Bening after decades of dating some of the most high-profile women in Hollywood — from Joan Collins to Diane Keaton and Madonna. While speaking to GQ in 2016, he addressed the earlier assumptions that he would never marry and said he was thankful he ignored outside opinions.

"Had I gone ahead earlier and gone through 143 divorces, I would have felt very guilty. I think I would have handled it badly," he said. "More importantly, it wouldn't have been these kids or this wife ... I'm so much more interested in my wife and kids than anything else."

November 22, 2016: Warren Beatty says his children with Annette Bening are his heroes

In a 2016 interview with PEOPLE, Beatty spoke about his relationship with his four children, sharing that they changed everything for him.

"That's the biggest thing that's ever happened to me," he said of becoming a father. "And their mother. That's bigger than fame, and it came not a moment too soon."

Beatty also praised his children in a 2016 interview with Vanity Fair. He called his older son Stephen a "revolutionary, a genius and my hero," and added, "as are all my children. They've always known I felt that way."

December 1, 2016: Warren Beatty says he and Annette Bening like to brag about their kids

While accepting the Kirk Douglas Award in 2016, Beatty and Bening gushed about their children. The actor began, "I became a devoted husband and father 25 years ago, and I have to say they have been the most enthralling years of my life, with our four fantastic kids."

Bening joined to say, "At the beginning, you think that you're there to teach them something, but then of course what you realize is it's all about you learning from them ... We're really proud of our children. So we brag about them when we can."

Before the ceremony, Beatty told PEOPLE, "We are married now for 25 years, and we have these four, what I like to call small eastern European countries that we negotiate with, and we send ambassadors, and we negotiate, and they're the best thing that's ever happened to me — they, and her."

September 13, 2018: Warren Beatty and Annette Bening attend the Life Itself premiere

Beatty and Bening stepped out together at the premiere of Life Itself in 2018. Their date night came after Bening affirmed that their age gap strengthened their relationship.

"He's 21 years older than I am and we've always been at different stages of life. He's got a lot of experience. But we're very different in many ways," she told the British newspaper The Times. "The crucial thing is that while we want many of the same things in life, we've thrived because we approach things very differently."

November 2019: Warren Beatty and Annette Bening adjust to an empty nest

By 2019, Beatty and Bening's four children were grown up and out of the home.

In an interview with AARP, Bening said that acclimating to the new stillness was tough for the pair. "I think we're both still adjusting to the quiet at home," she said.

Even before they were on their own again, Beatty told PEOPLE in 2018 while still having Isabel and Ella in their vicinity, "There’s something about the empty nest that makes you say, ‘Well, maybe I should go out and make a movie.' "

February 2, 2022: Annette Bening shares what she thought of Warren Beatty when they met

In 2022, Bening looked back on her first impression of Beatty. She told PEOPLE that the first thing she noticed was that "he was incredibly intelligent" and remarked, "Wow, this guy is so smart and so sharp and funny, but more — just articulate."

Bening added, "He was very talkative. He was very passionate about the movie that he was about to make. He had a lot to say — and he was charming, for sure."

February 11, 2022: Annette Bening shares her and Warren Beatty's Valentine's Day traditions

Bening shared about her Valentine's Day traditions with Beatty on The Kelly Clarkson Show in 2022.

She explained that the day is easy for the pair and said, "It's pretty no-pressure. Valentine's is pretty low-key. He will generally make me like a little Valentine with just a little red felt pen and make a little heart. He's very economical in his message."

As for Bening's gifts for Beatty, it turns out he's pretty hard to shop for. "There's nothing to buy for him. He's one of those men, you cannot find anything ... So, no, it's usually something small; it's a little note, it's a flower."

January 16, 2024: Annette Bening shares her first impression of Warren Beatty

On The Drew Barrymore Show in early 2024, Bening reflected on meeting Beatty for the first time over 30 years prior.

"I was going to meet him and he was incredibly intelligent. That was honestly ... the biggest aphrodisiac," she said. "Funny and super smart. Now, he is also very handsome. I thought, ‘Wow, this is quite a guy.’ "

Although she admired some of his traits, Bening said she wasn't intending to take their relationship further than friendship at first. "I really thought about it professionally when I first met him. I didn’t think that there would be, like, a thing between us," she said on the show.

Ultimately, Bening felt grateful they developed a deeper connection. "I think marriage is like the greatest thing and greatest challenge to really make it all work and to stay together, and that is the thing that I am so, so proud of with us," the actress added.