Douglas waited nine months to win Catherine Zeta-Jones, he says

By 
, October 8, 2026 
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Michael Douglas says he courted Catherine Zeta-Jones for nine months before intimacy, then ended five other relationships the day they made it official.

The Oscar-winning actor lays out the slow chase in his memoir and in related remarks, describing a first meeting tied to 1998’s The Mask of Zorro, a drawn-out courtship, and a monogamy condition she set before they became a couple. The Daily Mail carried the account drawn from that material and from a Sunday Times exchange.

Douglas was still mid-divorce from first wife Diandra Luker when he met Zeta-Jones. He was struck fast. She preferred to take it slow. That gap, and what he did about his other girlfriends, is the core of the story he is telling now.

Deauville dinner, then the longest courtship of his life

Douglas connected the meeting to the Deauville film festival, where he joined Zeta-Jones along with her Zorro co-star Antonio Banderas and Melanie Griffith for dinner and drinks. He had already read an interview in which she said she preferred older men. The 25-year age gap worried him. He still leaned in.

He blurted a line that night that he has never walked back.

"I’m going to be the father of your children"

What followed, he says, was not his usual pattern. He had long slipped straight into physical intimacy. With her, he waited.

"I looked forward to seeing her whenever I could. It wasn't that often, but I drank up every moment. What started as the two of us getting to know each other slowly turned into the longest courtship I had ever undertaken!"

He says he was willing to take whatever time both of them needed. He did not want her to become another ex on a long list, and she did not want him to become one on hers. Offsetting the “reputation” she had mentioned on night one mattered to him, he wrote, because she mattered.

Mallorca, monogamy, and five goodbye calls

In June 1999 he invited her to his holiday home in Mallorca. She kept her own bedroom at first. Friends Pat Riley, then president of the Miami Heat, and Riley’s wife, Chris, stayed as well. Douglas wanted her to see a steady married couple. He says that part worked.

They slept together for the first time on that trip. They became official only after she insisted on monogamy. He was seeing five other women at the same time, women who, he says, knew he was separated and heading toward divorce. He had kept them in different cities. None had asked for a commitment.

"That day, I called each one to say I'd met somebody and would no longer be able to continue seeing them. They all took it well."

He told his parents. His father, Kirk Douglas, called him a lucky b*****d. Her parents were supportive. Six months after the couple went public as exclusive, she was pregnant with their son Dylan.

Aspen flu, Plaza vows, and a one-career-at-a-time pact

He proposed in Aspen on New Year’s Eve 1999. Both had the flu. They married at the Plaza Hotel in New York three months after Dylan’s birth, with Cameron Douglas, Michael’s son with Diandra, then 21, as best man. Guests included Tom Hanks, Whoopi Goldberg, Anthony Hopkins, and Bonnie Tyler. The honeymoon was back in Aspen.

They struck a practical deal: only one of them would work heavily at a time so the kids had a parent at home. When she landed Chicago, he stayed home. She won the Oscar. Their daughter Carys was born the following year. He says that he had already carved out his film career and had nothing left to prove, and that it was her time.

Earlier marriages, on-set affairs, and a hard reset

The memoir does not skip the years that built the reputation Zeta-Jones had heard about. Douglas describes a passionate affair with married co-star Lee Purcell on 1970’s Adam at 6 A.M. while he was single. He spent about six years with Brenda Vaccaro after Summertree, then left after he believed she had been involved with actor Don Stroud.

He met Diandra Luker at a pre-inaugural party tied to President Jimmy Carter, married her within eight weeks in 1977, and had Cameron the next year. Kirk paid for a garden ceremony; the reception was at the Beverly Wilshire. That marriage ran until 1995. Along the way Douglas recounts an affair with Romancing the Stone screenwriter Diane Thomas, an on-set relationship with Kathleen Turner that he had denied in public for years and says he disclosed in the book only after asking her permission, another involvement during War of the Roses, and an affair with Jeanne Tripplehorn during Basic Instinct, not Sharon Stone, contrary to what many assumed.

In 1992, after Diandra caught him being unfaithful, she gave him a blunt choice: rehab or divorce. He went to rehab. The marriage still ended three years later. He later saw other women, including New York Times columnist Maureen Dowd, whom he praised for wit and remained friends with.

Cancer, a public stumble, and a marriage that bent but held

In 2010 he was diagnosed with stage 4 tongue cancer and beat it. Around 2013 he publicly blamed the cancer on oral sex; a publicist retracted the remark, and he later said he regretted embarrassing his wife. Two months after that episode, in August 2013, Zeta-Jones confirmed they were “taking some time apart to evaluate and work on their marriage.”

They were back together within a year. He says that he never gave up hope from the first day of the split.

"From the second we separated, I never gave up hope that we would reconcile. I love Catherine in a way that I have never loved any other woman. She’s my wife, my best friend, and my life partner. I could never lose her."

Asked by the Sunday Times whether he “won her back,” he pushed back on the framing.

"What, I won her back? It was a mutual... You know, we had our problems but I love her dearly and, 25 years, you know. Marriage is a lot of work, you know. And so, you know, we’re good. We’re in good shape. It’s all I can say."

His memoir, One Helluva Ride, is out now. Their 26th wedding anniversary is next month.

A Hollywood marriage that demanded monogamy up front, survived cancer and a public separation, and still gets described as hard work is not a fairy tale, it is a reminder that vows mean more when someone finally chooses one person and means it.

About Charles McAdams

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