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 film in Scotland and had roses and a card waiting for her when she arrived.
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.”
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.
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.
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.