Michael Douglas and Catherine Zeta-Jones' Relationship Timeline

Michael Douglas and Catherine Zeta-Jones attend the 73rd Primetime Emmy Awards at L.A. LIVE on September 19, 2021 in Los Angeles, California
Michael Douglas and Catherine Zeta-Jones attend the 73rd Primetime Emmy Awards at L.A. LIVE on September 19, 2021 in Los Angeles, California

Rich Fury/Getty

Oscar-winning actors Michael Douglas and Catherine Zeta-Jones share two children, a Sept. 25 birthday and over two decades of marriage.

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 2022, they celebrated 22 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," he added.

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

1998: Michael Douglas and Catherine Zeta-Jones meet

Catherine Zeta-Jones with her husband Michael Douglas; circa 1990; New York
Catherine Zeta-Jones with her husband Michael Douglas; circa 1990; New York

Art Zelin/Getty

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

Michael Douglas & Catherine Zeta-Jones
Michael Douglas & Catherine Zeta-Jones

SGranitz/WireImage

Roughly two years after the pair met, Douglas and Zeta-Jones welcomed their first child together, son Dylan Douglas, on Aug. 8, 2000, in Los Angeles. "They're ecstatic," Douglas' publicist said at the time.

November 18, 2000: Michael Douglas and Catherine Zeta-Jones get married at New York's Plaza Hotel

Michael Douglas and Catherine Zeta-Jones attend the 25th Anniversary of Saturday Night Live on September 26, 1999 in New York City.
Michael Douglas and Catherine Zeta-Jones attend the 25th Anniversary of Saturday Night Live on September 26, 1999 in New York City.

Kevin Mazur / Getty

The new parents tied the knot in an extravagant ceremony at the Plaza Hotel in New York City on Nov. 18, 2000. Plenty of celebrity guests attended the nuptials, including Tom Hanks, Whoopi Goldberg, Anthony Hopkins, Brad Pitt and Goldie Hawn.

Zeta-Jones wore a David Emanuel dress and Douglas' then-21-year-old son Cameron (from his previous marriage to Diandra Luker) served as the best man. The couple's then-3-month-old son Dylan was also in attendance.

September 2002: Michael Douglas and Catherine Zeta-Jones are expecting their second baby

Zeta-Jones discovered she was pregnant with her and Douglas' second child toward the end of filming Intolerable Cruelty. "I didn't want to know until I finished it," she told PEOPLE. "The day after, I went to my doctor. I came home and told Michael. He let out a whoop. I never wanted Dylan to be an only child. Because of my amazing relationship with my siblings, I couldn't see him being the Little Lord Dylan on his own."

March 23, 2003: Catherine Zeta-Jones thanks Michael Douglas in her Academy Award acceptance speech

Cathetine Zeta-Jones and Michael Douglas
Cathetine Zeta-Jones and Michael Douglas

Theo Wargo/WireImage

Douglas and Zeta-Jones attended the 75th annual Academy Awards on March 23, 2003, while the actress was pregnant with their second child.

Zeta-Jones performed "I Move On," from the Chicago soundtrack with costar and fellow nominee Queen Latifah, and then went on to snag the Oscar for Best Supporting Actress her role as Velma Kelly in the hit musical.

"I mean my hormones are just way too out of control for me to be dealing with this," Zeta-Jones joked in her speech, before thanking her family.  "And to my son Dylan who is going to be watching at home, and to my husband who I love, I share this award with you."

April 20, 2003: Michael Douglas and Catherine Zeta-Jones welcome a baby girl

The couple welcomed their second child together, daughter Carys Zeta Douglas, on Easter Sunday in 2003. The name Carys means love in Welsh (Zeta-Jones is from Wales). Carys was born in Ridgewood, New Jersey, near the family's Manhattan home.

September 1, 2010: Michael Douglas and Catherine-Zeta Jones open up about his throat cancer diagnosis

In September 2010, Douglas and Zeta-Jones spoke exclusively with PEOPLE following the Wall Street: Money Never Sleeps star's throat cancer diagnosis.

"It's a fight," Douglas said. "It really knocks you out." At the time, he was undergoing radiation and chemotherapy to treat a tumor at the base of his tongue.

Zeta-Jones added that watching her husband go through treatment was difficult. "The hardest part is seeing his fatigue, because Michael is never tired," she shared. "If there's anything Michael has, it's strength."

"I'll beat this," said Douglas.

September 30, 2010: Catherine Zeta-Jones says Michael Douglas is nearing the end of his cancer treatment

Michael Douglas (L) and Catherine Zeta-Jones attend the premiere of "Wall Street: Money Never Sleeps" at the Ziegfeld Theatre on September 20, 2010 in New York City.
Michael Douglas (L) and Catherine Zeta-Jones attend the premiere of "Wall Street: Money Never Sleeps" at the Ziegfeld Theatre on September 20, 2010 in New York City.

Jim Spellman / Getty

Later in September, Zeta-Jones said Douglas was "doing very well" since receiving his cancer diagnosis.

"He is holding up with strength and dignity," Zeta-Jones told PEOPLE at the Ryder Cup "Welcome to Wales" gala in her native country. "He is about to finish his treatment and the doctors could not be happier."

January 10, 2011: Michael Douglas is cancer-free

Michael Douglas (L) and wife actress Catherine Zeta-Jones attend Relativity Media and The Weinstein Company's 2011 Golden Globe Awards After Party presented by Marie Claire held at The Beverly Hilton hotel on January 16, 2011 in Beverly Hills, California
Michael Douglas (L) and wife actress Catherine Zeta-Jones attend Relativity Media and The Weinstein Company's 2011 Golden Globe Awards After Party presented by Marie Claire held at The Beverly Hilton hotel on January 16, 2011 in Beverly Hills, California

Frazer Harrison/Getty

In January 2011, Douglas revealed that he was cancer-free during an appearance on Today.

"I feel good, relieved," Douglas told Matt Lauer. "The tumor is gone. But, you know, I have to check out on a monthly basis now to maintain."

After his final cancer treatment, Douglas and Zeta-Jones took their children on a trip to Walt Disney World in Florida for Thanksgiving.

"All of a sudden the affection from my family, from my friends, and from my fans hit me at a much deeper level than I would have ever imagined before," the actor told Lauer. "And it gave me a really new appreciation of just how valuable, how precious good friends are, and family."

"There's a much deeper feeling," he continued. "And I've talked to other cancer survivors about this, that — that happens, that you just really, really appreciate what's important in life."

August 2013: Michael Douglas and Catherine Zeta-Jones split

After nearly 13 years of marriage, the couple announced their separation in August 2013. A source told PEOPLE that the stress —between Douglas' cancer battle and Zeta-Jones' struggles with her bipolar II disorder — had taken a toll on their marriage. "They're taking a break," the source added.

Douglas and Zeta-Jones had not been photographed together for four months prior to the announcement.

August 28, 2013: Michael Douglas returns to the place where he met Catherine Zeta-Jones

Shortly after their separation was announced, Douglas returned to the Deauville Film Festival where he and Zeta-Jones first met in 1998. Douglas' film, Behind the Candelabra, was scheduled to open the festival, and the star made the trek alone.

September 23, 2013: Michael Douglas says he and Catherine Zeta-Jones are "working things out"

Michael Douglas and Catherine Zeta-Jones attend the 2013 Vanity Fair Oscar Party hosted by Graydon Carter at Sunset Tower on February 24, 2013 in West Hollywood, California
Michael Douglas and Catherine Zeta-Jones attend the 2013 Vanity Fair Oscar Party hosted by Graydon Carter at Sunset Tower on February 24, 2013 in West Hollywood, California

Kevin Mazur/VF13/WireImage

Douglas attended the 65th Primetime Emmy Awards in 2013 solo. However, prior to the ceremony, he gave PEOPLE an update on his relationship status, saying, "We're working things out, talking, and we'll see how she goes."

Later in the evening, Douglas took home the award for outstanding lead actor in a miniseries or movie for his role as Liberace in Behind the Candelabra. In his speech, he made sure to mention Zeta-Jones, saying, "I want to thank my wife Catherine for her support."

April 21, 2014: Michael Douglas and Catherine Zeta-Jones attend the 14th annual Monte Cristo Awards together

By the end of April 2014, Douglas and Zeta-Jones had seemingly reconciled, and they walked the red carpet together at the 14th annual Monte Cristo Awards in N.Y.C. Just a week before, they made their first public appearance together since their split at the opening night of the play The Library at The Public Theater in N.Y.C.

While the couple's reps did not comment on if they were officially back together at the time, a close friend of the family told PEOPLE, "Things seem to be going really well for them. I knew they were going to work as hard as they could on their marriage, especially for the kids. It's a good thing."

April 16, 2015: Michael Douglas says he and Catherine Zeta-Jones are "stronger than ever"

Catherine Zeta Jones and Michael Douglas and their children Dylan and Carys attend the European Premiere of Marvel's "Ant-Man' at Odeon Leicester Square on July 8, 2015 in London, England
Catherine Zeta Jones and Michael Douglas and their children Dylan and Carys attend the European Premiere of Marvel's "Ant-Man' at Odeon Leicester Square on July 8, 2015 in London, England

Fred Duval/FilmMagic

A year after they got back together, Douglas opened up about the couple's split and reconciliation during an appearance on The Ellen DeGeneres Show.

"It can't be a one-way street," Douglas told 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."

He continued, "We're back stronger than ever."

November 18, 2015: Michael Douglas and Catherine Zeta-Jones celebrate 15 years of marriage

The Chicago star celebrated her 15th wedding anniversary with a loving tribute to Douglas on Instagram.

"Happy Anniversary dearest Michael! Loving our life together, here's to the next 15!" Zeta-Jones wrote alongside a photo of the two embracing as Douglas kissed her forehead.

Douglas honored their milestone anniversary a couple of weeks later at a luncheon at Le Bernardin in N.Y.C., where he accepted an AARP Movies for Grownups Career Achievement Award.

"I just wanted to thank my wife," Douglas joked during his acceptance speech. "I wanted to explain to Catherine that, sweetheart, this is a very exclusive club that maybe in a few years, if you play your cards right, you may be able to [join]."

As the audience laughed, Douglas added that he wanted, "to thank you as we celebrate our 15th wedding anniversary: Thank you for the love and all your support. Thank you so much."

March 16, 2016: Michael Douglas and Catherine Zeta-Jones return to the romantic spot where he proposed

Catherine Zeta-Jones (L) and Michael Douglas attend the 76th Annual Golden Globe Awards at The Beverly Hilton Hotel on January 6, 2019 in Beverly Hills, California
Catherine Zeta-Jones (L) and Michael Douglas attend the 76th Annual Golden Globe Awards at The Beverly Hilton Hotel on January 6, 2019 in Beverly Hills, California

Frazer Harrison/Getty

The long-time couple returned to the Rocky's where Douglas proposed to Zeta-Jones 16 years prior. The Entrapment star shared the moment on Instagram.

"16 years ago, this was the spot where my husband proposed," she captioned the photo of the two posing against a picturesque mountain backdrop.

December 18, 2017: Michael Douglas and Catherine Zeta-Jones become grandparents

In December 2017, Douglas and Zeta-Jones became grandparents when the actor's son Cameron and his girlfriend Viviane Thibes welcomed their first child together — a daughter named Lua Izzy.

Douglas couldn't contain his excitement when he told CBS, "I'm going to be a grandfather this month, before the end of the year. I'm very excited. It's about time."

January 6, 2019: Michael Douglas says his love for Catherine Zeta-Jones "continues to grow" after celebrating 18 years of marriage

Michael Douglas and Catherine Zeta-Jones attend the Netflix's 71st Emmy Awards After Party on September 22, 2019 in Hollywood, California
Michael Douglas and Catherine Zeta-Jones attend the Netflix's 71st Emmy Awards After Party on September 22, 2019 in Hollywood, California

Tommaso Boddi/Getty

Douglas revealed the secret to his long-lasting marriage with Zeta-Jones a few months after the pair rang in 18 years of marriage.

"We celebrated our 18th anniversary recently," Douglas told reporters at the 2019 Golden Globes, "and besides the genuine love that only continues to grow, I think the fact that we're in the same industry really helps us to understand what is going on."

"It was great for her to be here tonight and to share one of those nice things where your partner totally understands what's going on," he continued. "I flashed back to the time when she was pregnant with our daughter in Chicago and for all the award shows that were going on then."

He added, "The joy of my marriage with Catherine and having our children at a point in my life where my career had been developed, allowed me much more time to enjoy my family."

July 24, 2020: Catherine Zeta-Jones shares her 20th anniversary plans with Michael Douglas

Ahead of the couple's 20th wedding anniversary, Zeta-Jones spoke to PEOPLE about their plans for celebrating.

"We won't be doing any great big party," she said. "Not that I'm a big party fan anyway. It would be nice to get all our friends together in one space, but we're not doing that until we're completely out of the woods. So I will raise my mask and let my husband passionately kiss me, then I will put it firmly back on."

May 26, 2021: Michael Douglas and Catherine Zeta-Jones become empty nesters

Michael Douglas and Catherine Zeta-Jones attend the 78th Annual Golden Globe Awards held at The Rainbow Room and broadcast on February 28, 2021 in New York, New York
Michael Douglas and Catherine Zeta-Jones attend the 78th Annual Golden Globe Awards held at The Rainbow Room and broadcast on February 28, 2021 in New York, New York

Cindy Ord/NBCUniversal/NBCU Photo Bank via Getty Michael Douglas and Catherine Zeta-Jones

Douglas and Zeta-Jones celebrated their 18-year-old daughter Carys' graduation from high school and prepared for their next phase of parenting in May 2021.

The Basic Instinct star appeared on an episode of Today and opened up about becoming an empty nester with his wife.

"It's scary. It really is," Douglas said. "You look at each other and go, 'Well, it's just you and me babe.' "

He continued, "You forget how many conversations you sort of hide behind in terms of talking about your kids and what's going on next and this and that, and then one day you just look at each other ... We're 20 years now, so all those good years of paying attention to each other are paying off now."

September 19, 2021: Catherine Zeta-Jones celebrates Michael Douglas' Emmy nomination

While walking the carpet at the 73rd Primetime Emmy Awards, Zeta-Jones couldn't contain her excitement over Douglas' Emmy nomination for his work in The Kominsky Method.

"I always like to see my husband nominated on the red carpet, I've become a very proud wife," she told Karamo Brown.

November 21, 2021: Michael Douglas and Catherine Zeta-Jones celebrate Thanksgiving with their children

In November 2021, Zeta-Jones gave fans a glimpse into her Thanksgiving with Douglas and their two kids. "Happy Thanksgiving to all. So much to be thankful for," she captioned a video of their meal.

The family's Thanksgiving feast included the actress's "favorite" stuffed pears, prepared by Carys, as well as plenty of appetizers and festive table decorations.

February 2, 2022: Michael Douglas and Catherine Zeta-Jones vacation in the Dominican Republic

The couple took a family trip to the Dominican Republic in February 2022. Zeta-Jones shared a snap of Douglas, Dylan Michael and Carys posing in front of a waterfall.

September 25, 2022: Michael Douglas and Catherine Zeta-Jones celebrate their shared birthday

Both Douglas and Zeta-Jones were born on Sept. 25 and in 2022, the couple celebrated another trip around the sun with a huge birthday cake.

The tiered confection was covered in frosting, decorated with flowers and topped with two number candles making out "25."

"Thank you all for the kind birthday messages!" Douglas captioned a photo of the married pair blowing out birthday candles. "We love you all 🎂 ❤️."

November 16, 2022: Catherine Zeta-Jones opens up about her family life

Zeta-Jones attended the Los Angeles premiere of Wednesday on Nov. 16, 2022, and brought her son Dylan as her date.

"Well first of all, husband Michael is very happy that this is my date! A collaboration between the two of us, the gift that keeps on giving," Zeta-Jones told PEOPLE. "Both my daughter and Dylan have been so incredibly supportive to me, not just as an actor, but just me, you know."

She continued, "I've been extremely blessed to be able to have both in my life."

November 28, 2022: Michael Douglas and Catherine Zeta-Jones celebrate 22nd wedding anniversary

In honor of the couple's 22nd anniversary, Douglas shared photos from their November 2000 wedding on Instagram.

"Happy Anniversary to my darling Catherine! I love you so much," he captioned the throwback post.

In response, Zeta-Jones posted a recent photo of her and a shirtless Douglas kissing.

"22 years and 1 day! It's in the fine details..love you sweetheart. Happy Anniversary," she wrote on Instagram.