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Michael Douglas didn’t just choose Catherine Zeta-Jones — he called five other women in one day to make sure she was the only one.
The two-time Oscar winner pulls back the curtain on his extraordinary life in his new memoir, “One Helluva Ride,” revealing his struggle to escape his father Kirk Douglas’ towering shadow, his past affairs and drug use, his terrifying battle with stage IV cancer — and the highs and lows of his decades-long love story with the actress.
Douglas first fell head over heels for Zeta-Jones when she caught his eye in the 1998 movie “The Mask of Zorro.” Douglas, who is 25 years older than Zeta-Jones, later came across an interview in which she said she liked older men. He thought he had a chance.
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Catherine Zeta-Jones and Michael Douglas attend the launch of the new Aston Martin DB12 at the Hotel du Cap-Eden-Roc in Antibes on May 24, 2023, in Cannes, France. In his memoir, “One Helluva Ride,” Douglas revealed that he broke up with five women before embarking on a romance with Zeta-Jones. (David M. Benett)
Douglas went on to meet Zeta-Jones at the Deauville Film Festival in France. As the evening came to an end, Douglas blurted out, “I’m going to be the father of your children.”
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“One Helluva Ride” by Michael Douglas is available now. (Grand Central Publishing)
Zeta-Jones wasn’t exactly swept off her feet. She knew about Douglas’ reputation as a Hollywood womanizer and remained wary of his intentions. Douglas, however, was determined to convince her that this time he was serious.
Eventually, Zeta-Jones was willing to give Douglas a chance, but under one condition: he needed to be monogamous.
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“I’m not interested in dating you if you’re dating other people,” she told him. “You can either continue with them or end it and be with me.”
That day, Douglas wrote, he made five phone calls to five women he was seeing who lived in different cities.
Catherine Zeta-Jones attends a photocall for Martin Campbell’s movie “The Legend of Zorro” on Oct. 3, 2005, in Paris. “The Mask of Zorro” was released in 1998. (Getty Images)
“Just after my marriage, I had been seeing five other women,” he wrote. “They knew I was recently separated and in the process of getting a divorce. I made sure they all lived in different cities, which felt like a respectful way to be nonmonogamous. None of them asked for a commitment or even asked what else I was up to. I am sure they were seeing other people, too.”
Michael Douglas and Catherine Zeta-Jones during the F1 Grand Prix of Las Vegas at Las Vegas Strip Circuit on Nov. 21, 2025, in Las Vegas, Nevada. (Arnold Jerocki/Getty Images)
He told each woman he had met someone and could no longer see her. According to Douglas, “they all took it well.”
The couple married in 2000. They welcomed their son, Dylan, that year, followed by their daughter, Carys, in 2003. Today, the couple split their time between New York, Mallorca and Santa Barbara.
Michael Douglas and Catherine Zeta Jones visit Children’s Hospital for Wales in Cardiff, Wales, on June 20, 2006. (WireImage)
But their Hollywood love story hasn’t always been picture-perfect.
Carys Zeta Douglas, Michael Douglas and Catherine Zeta-Jones attend the “Jeanne du Barry” screening and opening ceremony red carpet at the 76th annual Cannes Film Festival at Palais des Festivals in Cannes, France, on May 16, 2023. (WireImage)
In the book, Douglas wrote that in 2013, the couple went on vacation and, upon returning, “had a heart-to-heart” about their relationship.
Catherine Zeta-Jones and Michael Douglas attend the 2019 Netflix Primetime Emmy Awards after-party at Milk Studios in Los Angeles, on Sept. 22, 2019. (Getty Images for Netflix)
“We had been married for more than a decade,” Douglas recalled. “We had just gone through a period where a number of challenges came at us all at once. We decided to take some time apart. We still loved each other immensely, but we needed to make sure that being married was the right thing for all of us.”
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Michael Douglas and Diandra Luker finalized their divorce in 2000, after which he married Catherine Zeta-Jones. (Arnold Jerocki/Getty Images)
“The entire ordeal was incredibly difficult,” Douglas wrote. “Catherine and I have a very intense, deep love for each other. And we love our kids dearly. We worked hard to make sure they understood that this wasn’t their fault. It wasn’t anyone’s fault. I had learned the hard way that staying together for the children isn’t always the right course of action. Sometimes you need to take a step back and make sure you’re doing what’s best for your whole family.”
Douglas and Zeta-Jones had weathered an extraordinarily difficult stretch for their family.
Michael Douglas is seen here sitting down for his first exclusive television interview since his cancer treatments. Douglas announced his stage IV cancer diagnosis on Aug. 16, 2010, and he has been in remission and cancer-free since January 2011. (NBC Newswire/NBCUniversal via Getty Images)
In 2010, Douglas was diagnosed with cancer. That same year, his eldest son, Cameron Douglas, was battling addiction and was sentenced to five years in prison after pleading guilty to drug charges. At the same time, Douglas was embroiled in a legal dispute with his ex-wife, Diandra Luker, over proceeds from “Wall Street: Money Never Sleeps.”
Michael Douglas and Diandra Luker were married for 23 years, from 1977 until their divorce was finalized in 2000. (Sygma via Getty Images)
In his memoir, Douglas acknowledged that the mounting pressure took a toll on his wife, writing that “all of that stress” was “heaped onto” Zeta-Jones.
Zeta-Jones and the couple’s two children, Dylan and Carys, stayed in the family’s home in Bedford, New York. Douglas rented another place nearby so he could still see the children. He and Zeta-Jones “spoke regularly, but not every day.”
From left: Catherine Zeta-Jones, Michael Douglas and Carys Zeta Douglas attend the “Jeanne du Barry” screening and opening ceremony red carpet at the 76th annual Cannes Film Festival at Palais des Festivals on May 16, 2023, in Cannes, France. (Stephane Cardinale – Corbis/Corbis via Getty Images)
“Part of taking a break is actually taking a break, something Diandra and I had struggled to do productively,” he wrote of his past marriage.
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From left: Dylan Michael Douglas, Michael Douglas and Cameron Douglas attend the Princess Grace Awards at The Pierre Hotel in New York City on Oct. 23, 2024. (Patrick McMullan via Getty Images)
“It was hard on the kids, and they were so strong during the entire ordeal,” Douglas wrote. “They knew that we both loved them more than anything, and their trust in us never wavered.”
As Douglas navigated the separation, he wrote that he never gave up hope that he and Zeta-Jones would reconcile.
Catherine Zeta-Jones and Michael Douglas attend the 17th Annual Night of Stars on Oct. 24, 2000, in New York City. The couple married Nov. 18, 2000, at New York’s Plaza Hotel. (Getty Images)
“I love Catherine in a way that I have never loved any other woman,” he wrote. “She’s my wife, my best friend, and my life partner. I could never lose her.”
Best supporting actress winner Catherine Zeta-Jones in the press room at the 75th Annual Academy Awards. She was pregnant with her daughter, Carys. (Joe Llano/WireImage)
“As Catherine and I were seeing each other more surrounding the kids — school functions, drop-offs, extracurricular activities — we realized we both missed each other enormously,” he wrote. “Taking time away helped reignite the spark that had brought us together.”
The couple reconciled in 2014.
Catherine Zeta-Jones and Michael Douglas attend the “Entrapment” premiere at the Odeon cinema in Edinburgh, Scotland, on June 30, 1999. (Mirrorpix via Getty Images)
“Thank God we found our way back to each other,” Douglas wrote. “Our marriage deserved a second chance. Today, our marriage is stronger than ever, and we recently celebrated our 25th wedding anniversary. We still love spending time together. We can play 18 holes or walk on the beach, or we can just sit on the couch all day long talking. After all these years, wherever we are in the world, Catherine Zeta-Jones is still an incredible date.”
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Catherine Zeta Jones and Michael Douglas stand on the second hole of The Old Course before the Alfred Dunhill Links Championship 2025 in St. Andrews, Scotland, on Sept. 30, 2025. (Getty Images)
After decades together, Douglas told Fox News Digital he has learned a major lesson about making a marriage last in Hollywood.
“Making that person, that partner, as special as 25 years later,” he said. “Make her feel as special 25 years later as the first day you started wooing her. What happens sometimes, after a while, is compatibility, and we end up making more of an effort with strangers than the person closest to you. So, I think it really calls for mutual respect and a good sense of humor.”
Michael Douglas attends the Women In Cinema event during the Red Sea International Film Festival 2024 in Jeddah, Saudi Arabia, on Dec. 6, 2024. (Getty Images)
When asked what Zeta-Jones, 57, does that still makes him feel like the luckiest guy in the world, he didn’t miss a beat.
Catherine Zeta-Jones and Michael Douglas attend the “Ant-Man and the Wasp: Quantumania” UK gala screening at BFI IMAX Waterloo in London, England, on Feb. 16, 2023. (Samir Hussein/WireImage)
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“Walk into a room,” he said with a smile.