Michael Douglas (82) Was Juggling 5 Women When Catherine Zeta-Jones (57) Handed Him an Ultimatum, and He Had Just 1 Day to End It All

Every great Hollywood romance has an origin story, but few include a deadline. Michael Douglas has spent decades as one of the industry’s most recognizable leading men, and his reputation for a playboy lifestyle followed him for years. His new memoir, ‘One Helluva Ride’, now reveals the moment that reputation finally collided with Catherine Zeta-Jones.

The book, which arrived on Oct. 6, covers his childhood as Kirk Douglas’s son, his biggest films, his first marriage, infidelity, rehab and his cancer battle. Excerpts have been circulating all week, and some of them have already reopened old chapters of his personal life, including an admission about an affair with Kathleen Turner on the set of ‘Romancing the Stone’.

Among the most talked-about passages is the one describing the early days of his relationship with Zeta-Jones. According to the excerpts, she made her position crystal clear: she would only be monogamous, and she wasn’t interested in dating him if he was seeing other people. His choice, in other words, was to keep going with his other relationships or end them and be with her.

It was a stunning demand for a man who, by his own account, had been enjoying a very different lifestyle. Douglas writes that the timing was complicated, since he had recently separated from his first wife, Diandra, and was in the middle of a divorce. Reports say they separated in 1995, with the divorce finalized in 2000.

Douglas says he wasn’t dating one woman at the time. He describes seeing several women at once, each living in a different city, and says all of them knew about his separation and divorce. He also says none of them asked for a commitment, and he assumed they were seeing other people as well.

He has described the setup as a respectful way to be non-monogamous, a phrase that will likely raise eyebrows with some readers. Still, the arrangement ended the moment Zeta-Jones laid down her condition. According to the memoir, Douglas asked her to wait while he made some quick phone calls, and she reacted with disbelief when she learned how many calls there were.

Douglas says he went through his list that same day, telling each woman that he had met someone and could no longer see them. He writes that all of them took it well. The reaction speaks to how casual the arrangement apparently was, though it’s worth remembering that this is Douglas’s own account and none of the women have spoken publicly about it.

The LA Times has reported that Douglas described himself as a new man after meeting Zeta-Jones and starting a family. It’s a tidy redemption narrative, and it fits the way the couple has presented their story for more than 2 decades.

The couple’s timeline moved quickly. They met in 1998 at the Deauville American Film Festival in France, where Douglas has said he was already a fan after seeing her in ‘The Mask of Zorro’. By his own account, he told her early on that he would be the father of her children, a line he later insisted was the truth.

They became engaged in December 1999 and married on Nov. 18, 2000, at the Plaza Hotel in New York City. Their son, Dylan, arrived that year, followed by daughter Carys in 2003.

The story isn’t a fairy tale without bumps. The couple separated in 2013 but never filed for divorce, and they reconciled in 2014. Douglas has said the reunion was mutual and that they are in good shape today.

That resilience may be why this particular anecdote is landing so well. It offers a glimpse of the moment a famous bachelor chose commitment, and it also shows the strong-willed woman who asked him to prove it. Zeta-Jones, for her part, has joked that she has no plans to read the book herself.

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