Michael Douglas…he had his publicist set up a date and although their first meeting didn’t quite go as planned, the pair eventually welcomed a child and tied the knot in 2000

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Catherine Zeta-Jones’ Relationship Timeline
Michael Douglas and Catherine Zeta-Jones have been married since 2000 and share two children

Michael Douglas and Catherine Zeta-Jones met in 1998 at the Deauville Film Festival
Douglas and Zeta-Jones got engaged in December 1999 and married the following November
Douglas and Zeta-Jones share two children: son Dylan and daughter Carys
They separated in August 2013 but reconciled in 2014
Oscar-winning actors Michael Douglas and Catherine Zeta-Jones share two children, a Sept. 25 birthday and they’ve been married for more than two decades.

The Fatal Attraction star immediately knew Zeta-Jones was the one after watching her in The Mask of Zorro in 1998. He had his publicist set up a date and although their first meeting didn’t quite go as planned, the pair eventually welcomed a child and tied the knot in 2000.

They went on to have another child, and in November 2023, they celebrated 23 years of marriage. However, the Hollywood power couple’s long-lasting relationship hasn’t been without its bumps in the road. In 2013, Douglas and Zeta-Jones briefly split before reconciling the following year.

Douglas opened up about the split and reconciliation during a 2015 appearance on The Ellen DeGeneres Show.

“It can’t be a one-way street,” Douglas told host Ellen DeGeneres. “But I’m crazy about her. And yeah, I think every couple has their difficult times. The only problem is, as you well know, we’re all in the public eye, and it tends to get a little more exposed than most. We’re back stronger than ever.”

Here’s a timeline of Michael Douglas and Catherine Zeta-Jones’ relationship through the years.

Douglas initially struck out when the pair met at the Deauville Film Festival in 1998. Zeta-Jones was promoting her film The Mask of Zorro and Douglas was promoting A Perfect Murder. During a 2016 appearance on The Jonathan Ross Show, Douglas revealed that he’d seen Zeta-Jones in her role as Elena Montero and asked his publicist to arrange a meeting.

“I met her in the bar and was a total gentleman,” Douglas said. He recalled asking her, “By chance do you want to come back and have a nightcap?” When Zeta-Jones met him later that night, he told her, “You know, I’m going to be the father of your children.”

According to Douglas, she responded, “You know I’ve heard a lot about you, and I’ve seen a lot about you, and I think it’s time that I say goodnight.” He thought he’d blown his shot with the actress, but he knew she was off to film Entrapment on a small island in Scotland, so he arranged to have roses waiting for her when she arrived.

“You know what the worst thing is?” Zeta-Jones joked during a red carpet interview with Access in 2019. “He was right.” Two decades later, Zeta-Jones still has the card that was attached to those roses.

December 1999: Michael Douglas and Catherine Zeta-Jones get engaged
While on a New Year’s Eve trip to Aspen, Colorado, Douglas proposed to the actress.

2000: Michael Douglas and Catherine Zeta-Jones are expecting their first baby together
After rumors circulated that the newly-engaged couple were expecting a baby, Douglas confirmed the pregnancy news to PEOPLE. “We obviously were hoping to hang onto this information a little longer than expected but, yep, Catherine’s expecting, and both of us couldn’t be happier,” said the actor.

August 8, 2000: Michael Douglas and Catherine Zeta-Jones welcome their first baby together.

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