The night Michael Douglas first met Catherine Zeta-Jones back in 1998, he told her, "I'm going to be the father of your children" — and while the pick-up line didn't work on the actress at the time, it turned out he was ultimately right. 

Fast forward to the present day, and Douglas and Zeta-Jones have been married for years with two kids — a son, Dylan, and a daughter, Carys — despite a few bumps along the way. Their love has endured for decades, overcoming obstacles like a 25-year age difference, a cancer diagnosis, and a brief split in 2013, making them one of the most steady couples in Hollywood. “True love takes work,” Douglas famously once said.

Here, take a complete look back at Michael and Catherine's longtime romance. 

August 1998: Michael Douglas and Catherine Zeta-Jones meet for the first time

Douglas and Zeta-Jones first met at the 1996 Deauville Film Festival in France by mutual friends and former couple Antonio Banderas and Melanie Griffith.

During a 2016 appearance on The Jonathan Ross Show, Douglas revealed, however, that he almost blew his shot with Zeta-Jones entirely. "I met her in the bar and was a total gentleman," Douglas said, explaining that he asked her back to his place for a nightcap. Zeta-Jones agreed, and shortly into the conversation, Douglas told her, "You know, I'm going to be the father of your children."

The line didn't work, and Zeta-Jones 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." Putting himself out there for a second time, Douglas found out she was going to be shooting a filmin Scotland and had roses and a card waiting for her when she arrived.

December 1999: Michael Douglas and Catherine Zeta-Jones get engaged

Douglas proposed to Zeta-Jones on New Year's Eve at his home in Aspen, Colorado. She said 'yes.'

August 2000: Michael Douglas and Catherine Zeta-Jones welcome their first baby together

The couple welcomed their first child, a son Dylan Douglas, on August 8, 2000, in Los Angeles. 

November 2000: Michael Douglas and Catherine Zeta-Jones get married

Nearly one year after their engagement, Douglas and Zeta-Jones wed at the Plaza Hotel in New York City. It was the event of the year with celebrity attendees, including Goldie Hawn, Jack Nicholson, Barbara Walters, and Tom Hanks. The couple's three-month-old son also took part in the festivities.

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

Zeta-Jones found out she was pregnant again while filming Intolerable Cruelty. "I didn't want to know until I finished it," she previously 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."

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

Zeta-Jones and Douglas welcomed their second child together, daughter Carys Zeta Douglas, on Easter Sunday in 2003 in New Jersey, near the couple's Manhattan home.

August 2010: Michael Douglas is diagnosed with throat cancer

Douglas was diagnosed with stage IV squamous cell carcinoma oral cancer, also known as throat cancer.

In an interview with People, Zeta-Jones said that watching her husband undergo radiation and chemotherapy 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."

By January 2011, Douglas announced he was officially cancer-free. After his final cancer treatment, Douglas and Zeta-Jones took their two children on a trip to Disney World for Thanksgiving to celebrate.

April 2011: Catherine Zeta-Jones is diagnosed with bipolar disorder

Amid the stress from her husband's cancer battle, Zeta-Jones sought treatment for bipolar II disorder. “After dealing with the stress of the past year, Catherine made the decision to check in to a mental health facility for a brief stay to treat her Bipolar II disorder,” her rep said in a statement at the time. “She’s feeling great and looking forward to starting work this week on her two upcoming films.”

A year later, she spoke to InStyle about her diagnosis. “I’m not the kind of person who likes to shout out my personal issues from the rooftops. But with my bipolar becoming public, I hope fellow sufferers will know it’s completely controllable,” she told the magazine. “I hope I can help remove any stigma attached to it.”

August 2013: Michael Douglas and Catherine Zeta-Jones split

After nearly 13 years of marriage, Douglas and Zeta-Jones decided to "take a break" from their relationship. The news was announced after it was observed that the two hadn't been photographed together in over four months and were taking a solo vacation with their kids. According to a source at People, Douglas's cancer battle and Zeta-Jones's bipolar diagnosis had taken a toll on their marriage.

April 2014: Michael Douglas and Catherine Zeta-Jones make their first public appearance since seemingly reconciling

Douglas and Zeta-Jones appeared to be back together after attending their first red-carpet event together at the opening night of the play The Library at The Public Theater in New York City.

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

A year after they separated, Douglas confirmed that he and Zeta-Jones were back and better than ever during an appearance on The Ellen DeGeneres Show.

"It can't be a one-way street," Douglas explained. "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 added, "We're back stronger than ever."

Later that year, the two celebrated their 15-year wedding anniversary.

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

On December 18, 2017, Michael became a grandfather, and Zeta-Jones, a step-grandmother after the actor's son from his first marriage to Diandra Luker, Cameron Douglas, and his girlfriend Viviane Thibes welcomed a daughter named Lua Izzy.

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

Douglas and Zeta-Jones were both born on September 25th — so to celebrate her 53rd birthday and his 78th, the couple jointly blew out the candles on a massive chocolate cake together.

May 2023: Michael Douglas and Catherine Zeta-Jones make a rare red carpet appearance with their daughter, Carys

Douglas and Zeta-Jones — along with their 20-year-old daughter Carys — attended the opening night of the Cannes Film Festival, where the actor was being honored with the Palm D'or Award. Zeta-Jones wore a plunging crimson Elie Saab gown that matched the red carpet, while Carys mirrored her mom's style in a white lace dress with side cutouts. Douglas, for his part, kept it classic in a black tux.