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

Oscar-winning actorsMichael DouglasandCatherine Zeta-Jonesshare two children, a Sept. 25 birthday and they’ve been married for more than two decades.

TheFatal Attractionstar immediately knew Zeta-Jones was the one after watching her inThe Mask of Zorroin 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 2023, they celebrated 23 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 onThe 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.”

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

1998: Michael Douglas and Catherine Zeta-Jones meet

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

Douglas initially struck outwhen the pair met at the Deauville Film Festivalin 1998. Zeta-Jones was promoting her filmThe Mask of Zorroand Douglas was promotingA Perfect Murder. During a 2016 appearance onThe 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 filmEntrapmenton 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 duringa red carpet interview withAccessin 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.

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Michael Douglas & Catherine Zeta-Jones

Roughly two years after the pair met, Douglas and Zeta-Jones welcomed their first child together, sonDylan 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

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

The new parentstied the knotin an extravagant ceremony at the Plaza Hotel in New York City on Nov. 18, 2000. Plenty of celebrity guests attended the nuptials, includingTom Hanks,Whoopi Goldberg,Anthony Hopkins,Brad PittandGoldie 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.

Zeta-Jones discovered she waspregnant with her and Douglas' second childtoward the end of filmingIntolerable 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

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Cathetine Zeta-Jones and Michael Douglas

Douglas and Zeta-Jones attended the75th annual Academy Awardson March 23, 2003, while the actress was pregnant with their second child.

“I mean my hormones are just way too out of control for me to be dealing with this,” Zeta-Jonesjoked 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.”

The couple welcomed their second child together, daughterCarys 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 theWall Street: Money Never Sleepsstar’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 isnevertired,” 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

Jim Spellman / Getty

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.

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

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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

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

“I feel good, relieved,” Douglas toldMatt 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 coupleannounced their separationin August 2013. A source told PEOPLE that the stress —between Douglas' cancer battle and Zeta-Jones' struggles with herbipolar 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, Douglasreturned to the Deauville Film Festivalwhere 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”

Kevin Mazur/VF13/WireImage

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

Douglas attended the 65th PrimetimeEmmy Awardsin 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 inBehind 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 playThe Libraryat 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”

Fred Duval/FilmMagic

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

A year after they got back together, Douglas opened up about the couple’s split and reconciliation during an appearance onTheEllen DeGeneresShow.

“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

TheChicagostar 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.

“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

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

“16 years ago, this was the spot where my husband proposed,” shecaptioned the photoof 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-Jonesbecame grandparentswhen the actor’s son Cameron and his girlfriendViviane Thibeswelcomed 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

Tommaso Boddi/Getty

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

Douglasrevealed the secretto 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 inChicagoand 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 abouttheir 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.Cindy Ord/NBCUniversal/NBCU Photo Bank via Getty

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

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

TheBasic Instinctstar appeared on an episode ofTodayand 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 PrimetimeEmmy Awards, Zeta-Jones couldn’t contain her excitement over Douglas' Emmy nomination for his work inThe 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 aglimpse into her Thanksgivingwith Douglas and their two kids. “Happy Thanksgiving to all. So much to be thankful for,” she captioned a video of their meal.

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

The couple took afamily trip to the Dominican Republicin 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 ahuge 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 L.A. premiere ofWednesdayon 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 blessedto be able to have both in my life.”

November 18, 2022: Michael Douglas and Catherine Zeta-Jones celebrate their 22nd wedding anniversary

In honor of the couple’s 22nd anniversary, Douglas shared photos from theirNovember 2000 weddingon 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 ofher 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.

December 5, 2022: Catherine Zeta-Jones talks about her happy family life with Michael Douglas

Zeta-Jonesspoke about her familywhile at theNational Treasure: Edge of Historypremiere in Hollywood, which she attended with her son, Dylan.

“I enjoy every minute with this guy. Well, he’s a good son. It’s just the best,” the actress said of her son, adding, “I mean, each year gets better and better and with such good friends, I think, in our family, which is great.”

February 6, 2023: Catherine Zeta-Jones supports Michael Douglas atAnt-Man3premiere

Douglas and Zeta-Jones walked the red carpet at theworld premiere ofAnt-Man and the Wasp: Quantumaniain L.A. This is the thirdAnt-Manfilm that Douglas has starred in.

March 2, 2023: Michael Douglas says Catherine Zeta-Jones makes him “whip it out” when they golf together

In 2016, while appearing onThe Graham Norton Show, Zeta-Jones told the host that she makes her husband “take his pants off” if he doesn’t hit the golf ball far enough.

“The rules areI have to whip it out if I don’t hit it past the ladies' tees, which I manage most of the time,” theAnt-Man and the Wasp: Quantumaniastar toldThe Guardian. “But there have been times when we’re playing alone, and [I] have to give her a little show because we are competitive.”

May 16, 2023: Michael Douglas and Catherine Zeta-Jones attend the Cannes Film Festival

Neilson Barnard/Getty

CANNES, FRANCE - MAY 16: Catherine Zeta-Jones, Michael Douglas and Carys Zeta Douglas attend the “Jeanne du Barry” Screening & opening ceremony red carpet at the 76th annual Cannes film festival at Palais des Festivals on May 16, 2023 in Cannes, France. (Photo by Neilson Barnard/Getty Images)

Zeta-Jones, along with their daughter Carys, walked the red carpet with Douglas on opening night of the Cannes Film Festival. Later that evening, Douglas washonored with the Palm D’or award.

“Cannes! Cannes! What a soirée! To walk the iconic red carpet with my daughter @carys.douglas and my husband @michaelkirkdouglas as he receives his lifetime achievement Palm D’or, was a night I shall never forget, ever,” Zeta-Jones wrote onInstagram.

July 31, 2023: Michael Douglas and Catherine Zeta-Jones enjoy a vacation in Italy

The couple were spottedwalking hand-in-hand in Portofino, Italy. Zeta-Jones dazzled in a plunging, purple maxi dress, while Douglas wore a blue button-down shirt and white trousers.

November 18, 2023: Michael Douglas and Catherine Zeta-Jones celebrate 23 years of marriage

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Catherine Zeta-Jones Celebrates 23 Years of Marriage to Michael Douglas: ‘Darling Michael, Your Nobel Peace Prize Awaits’

In honor of their wedding anniversary, Douglas and Zeta-Jones penned sweet posts about each other on Instagram.

“Today we celebrate 23 years of marriage. Darling Michael, your Nobel Peace Prize awaits. I love you…from your darling wife, a gold star Medal of Honor recipient,” she jokingly captioned a series of throwback images, including two from the couple’s wedding day.

Douglas’ post read: “Happy 23 and Me, my darling @catherinezetajones!Can’t wait for 24!”

February 14, 2024: Michael Douglas and Catherine Zeta-Jones celebrate Valentine’s Day

Catherine Zeta-Jones/Instagram

Catherine Zeta-Jones Wishes ‘My Love’ Michael Douglas a Happy Valentine’s Day with Romantic Photos

In honor of Valentine’s Day, Zeta-Jones penned a sweet post about her husband on Instagram.

“Happy Valentines Dayto my love Michael,” she captioned a montage of photos with Douglas. “Sealed with a kiss.” TheBasic Instinctactor responded to his wife’s gesture in a separateInstagrampost, writing, “Happy Valentine’s Day to my darling Catherine! Love you always and forever.”

source: people.com