Michael Douglas’ Staggering Relationship History Is a Who’s Who of Hollywood Legends

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Michael Douglas is opening up about a complicated romantic history that includes two marriages, long-term relationships, affairs, and connections with some of Hollywood’s most recognizable actresses.

The 82-year-old actor shares new details about his personal life in his memoir, “One Helluva Ride,” including a relationship with a famous co-star that he says remained secret for 40 years.

Douglas’ romantic history stretches back decades. Before marrying Catherine Zeta-Jones in 2000, he had a nearly six-year relationship with actress Brenda Vaccaro and a 23-year marriage to Diandra Luker. He has also acknowledged relationships with women he met while working in Hollywood.

Some of the biggest revelations involve what happened behind the scenes of his movies. Douglas confirms that his chemistry with one leading lady went beyond acting, while another actress nearly landed a role that became one of the defining films of his career.

His relationship with Zeta-Jones eventually marked a turning point, but getting there required Douglas to make a major change to his personal life.

Brenda Vaccaro and Michael Douglas Were Together for Nearly 6 Years Before His First Marriage

One of Douglas’ earliest significant Hollywood relationships was with Brenda Vaccaro.

The actors began dating after working together on the 1971 movie “Summertree.” Their relationship lasted nearly six years before ending in 1977.

That same year, Douglas married Diandra Luker, the daughter of an Austrian diplomat. The couple welcomed their only child together, Cameron Douglas, in 1978.

Douglas and Luker remained married for more than two decades, although their relationship eventually became troubled.

Luker filed for divorce in 1995, and their divorce became final in 2000. The settlement was reportedly worth $45 million.

In “One Helluva Ride,” Douglas provides additional insight into the problems within their marriage, acknowledging that both he and Luker became involved with other people.

“Things at home were in a bad place,” Douglas writes. “Diandra and I were both having extramarital affairs, including my recent romance with Diane Thomas [‘Romancing the Stone’s’ screenwriter].”

One of Douglas’ other relationships during that period involved a woman who became one of his most famous co-stars.

The ‘Wall Street’ Star Confirms His Secret Kathleen Turner Affair

Douglas and Kathleen Turner became one of the most memorable movie pairings of the 1980s after starring together in 1984’s “Romancing the Stone.”

Their chemistry continued in “The Jewel of the Nile” and “The War of the Roses,” fueling speculation that their connection extended beyond the screen.

For decades, Douglas and Turner denied having an affair. Douglas now says that story was not true.

“Kathleen was smart, funny, and sexy with a deep, sultry voice that became her signature,” Douglas writes. “I instantly liked her, and we were immediately attracted to each other.”

Douglas said he traveled to Mexico to make “Romancing the Stone” while still technically married to Luker but separated.

“The chemistry I had with Kathleen Turner was so strong, audiences have been certain for years that we were in a relationship together while making the film,” he writes.

Douglas said the pair continued denying it even years later while promoting “The Kominsky Method.”

“That was a lie,” Douglas writes.

He said they kept the relationship secret because he wanted to protect Luker and Cameron.

“The truth is that during the production of ‘Romancing the Stone,’ Kathleen and I fell hard for each other and began a relationship,” Douglas writes. “It wasn’t a fly-by night affair; it grew naturally from how closely we were working together, how much pressure we were under, how much we respected and cared for one another, and how attracted we were to each other.”

Douglas has also acknowledged an affair with his “Basic Instinct” co-star Jeanne Tripplehorn.

Debra Winger Nearly Changed Michael Douglas’ ‘Romancing the Stone’ Story

Turner might never have become Douglas’ “Romancing the Stone” leading lady if his original casting plan had worked out.

Douglas recalls courting Debra Winger to play romance novelist Joan Wilder. After a margarita-fueled dinner, he initially became convinced she was right for the role.

His thinking changed after hearing stories from the production of “Terms of Endearment,” in which Winger starred opposite Shirley MacLaine.

“Stories had filtered back that Debra was delivering an incredible performance in ‘Terms of Endearment,’ but also that she was difficult during shooting and had huge, blow-out fights with Shirley MacLaine,” Douglas writes.

Douglas was concerned because “Romancing the Stone” required a demanding production schedule.

“We knew it would be a lot to ask of any actress, and we were going to need somebody incredibly cooperative,” he writes.

Douglas claims an encounter with Winger ultimately ended any possibility of casting her. When director Robert Zemeckis later asked about Winger, Douglas recalled explaining his decision.

“She bit me. Hard. Look at the teeth marks in my arm,” Douglas said. “I can’t. She’s a gifted actress, but I am hearing a lot of bad stories from the set of ‘Terms of Endearment.’ I don’t care if she wants to do it.”

Turner ultimately got the role, beginning a professional and personal relationship that remained part of Douglas’ life for years.

Catherine Zeta-Jones Gave Michael Douglas a Choice About Their Future

Douglas’ personal life entered a new chapter when he met Catherine Zeta-Jones at the Deauville American Film Festival in France in 1998 after Danny DeVito introduced them.

Douglas made his intentions known almost immediately.

“I’m going to be the father of your children,” he recalled telling Zeta-Jones over a drink.

The line did not initially impress her. According to Douglas, Zeta-Jones walked out.

Douglas writes that he was not trying to use a pickup line.

“It wasn’t a cheap pickup line,” he writes. “It was the truth.”

“Because even though I had only gotten to know her in one evening … there was something completely different about her,” Douglas explains. “Different from any other woman I had ever met.”

Douglas eventually sent Zeta-Jones flowers with an apology note, and their courtship continued.

But Zeta-Jones eventually made one thing clear: If Douglas wanted a serious relationship with her, it had to be monogamous.

“I’m not interested in dating you if you’re dating other people,” Zeta-Jones told him, according to Douglas.

That presented a complication.

Following his 1995 separation from Luker, Douglas said he had been maintaining non-monogamous relationships with five women who lived in different cities.

“Wait here I have to make five quick calls,” Douglas recalled telling Zeta-Jones.

“Five? You have to make five calls?!” she responded.

Douglas made them.

“That day, I called each one to say I’d met somebody and would no longer be able to continue seeing them,” he writes. “They all took it well.”

Douglas Says Catherine Zeta-Jones Was ‘The One’

Douglas’ decision to commit to Zeta-Jones led to a relationship that has lasted for more than 25 years.

The couple became engaged in December 1999 and married at the Plaza Hotel in New York City on November 18, 2000.

Douglas said his certainty about Zeta-Jones went beyond their physical attraction.

“She was magic, in a way that went beyond beauty,” Douglas writes. “I was certain, as much as I had ever been about anything, that she was the one.”

Douglas and Zeta-Jones welcomed their son, Dylan Douglas, in 2000 and their daughter, Carys Douglas, in 2003.

Their marriage has also endured a difficult period. The couple briefly separated in August 2013 before reconciling in 2014.