Inside Charlie Sheen and Denise Richards' Relationship: From Their First Meeting to Their Reunion

Charlie Sheen and Denise Richards connected 25 years ago.

They met on the set of Good Advice in 2000, though they only struck up a romance when Richards guest-starred on Sheen's series Spin City the following year.

In an interview with People, The Real Housewives of Beverly Hills alum recalled watching the San Francisco Giants game at his condo for their first date.

"I made the first move kissing him," she confessed. "He was Mr. Polite, such a gentleman."

It was during the second date when Richards knew he was "The One."

"I knew that this is the one, but I wouldn't tell him that. I didn't want to scare him away by saying, 'You're my future husband!' and have him run for the hills," she continued.

The Two and a Half Men actor also opened up about their first date in his debut memoir, The Book of Sheen.

"I carefully explained to D that if we were at a restaurant unable to watch, the main thing on my mind would be the game. (The main thing I could say out loud.)," he wrote. "She completely understood and loved the idea of joining me to celebrate my passion for baseball. We ate our Zone meals from plastic bowls and hung on every pitch when Bonds was at the plate."

Sheen added, "As we were saying good night at the elevator, D grabbed my face and pulled me into a long passionate kiss. The Baseball Gods had sprinkled some magic on our night. I was no longer thinking about the game."

Less than three months after their first date, Sheen got down on one knee during a spa vacation in Arizona.

"I have one more Christmas gift for you," Richards recalled Sheen telling her, adding, "When he pulled a box out, I knew. I wanted to scream 'Yes,' but I wanted to hear all the words."

On June 15, 2002, Sheen and Richards officially became husband and wife after exchanging vows during an outdoor ceremony at Spin City creator Gary David Goldberg's Brentwood, Calif., estate.

Their first daughter, Sami Sheen, was born on March 9, 2004, over a year after their marriage.

A few months after they announced their second pregnancy, the Drop Dead Gorgeous actress filed for divorce from Charlie, citing irreconcilable differences.

"We are deeply saddened by the recent events and out of our love and concern for our daughter Sam, our unborn child and each other, we ask that you respect our privacy during this difficult time," a representative for the Red Dawn actor said.

In an episode of RHOBH years later, Denise shared what it felt like when she decided to end their marriage while she was pregnant with their second child.

"When I got pregnant with Lola, things started to change rapidly. It was a very dark time and very toxic," Denise said in a confessional. "And I filed for divorce when I was six months pregnant with her. I always did whatever I could to hide Charlie's behavior."

On June 1, 2005, Charlie and Denise expanded their family when they welcomed their second child, Lola Sheen.

"We're thrilled to finally meet our beautiful daughter," they said in a statement.

Charlie also shares daughter Cassandra Jade Estevez with his high school girlfriend Paula Profit and twins, Bob and Max Sheen, with his third wife, Brooke Mueller.

In an interview with Extra, the Eight Men Out actor confirmed they were looking at a potential reconciliation after Denise gave birth to Lola.

"Things are a whole lot better, and I think with that (comes) hope," he said. "We're not ruling anything out."

A source also claimed Denise "never wanted to get divorced" and "always hoped they could save their marriage."

Charlie and Denise's efforts to save their marriage appeared to have failed as they moved forward with their divorce.

After hiring a private arbiter in January 2006, Charlie and Denise gave fans an update regarding their relationship status.

"Denise and Charlie are working with the Courts to privately resolve their differences regarding their children," their representative shared in a statement. "They hope to resolve this matter outside of the public forum and will both continue to make every effort in this regard."

On November 30, 2006, they became legally free to marry other people. The divorce was not completely finalized at the time due to unresolved division of assets and custody agreement.

Amid the custody battle, Denise filed legal documents in which she accused her ex-husband of "inappropriate" behavior and conduct, like "his attraction to underage women and his sexual explicitness on the internet, including revealing his private parts."

With that, she asked the court to protect Sami and Lola as well as revoke his parental privileges.

On the other hand, Charlie hit back in a statement, saying, "Clearly the mother of my children has no interest in responsible co-parenting when it comes to my relationship with our girls."

On Father's Day in 2015, Charlie called out Denise after she allegedly called him a "deadbeat dad."

"Open letter to the media," he wrote on X, then-Twitter. "Denise Richards is a shake down piece of s--- doosh phace & worse mom alive! A despicable charlatan who sux ISIs a--."

Charlie then compared Denise to Brooke in a second tweet: "Brooke M is a s--- star whom I adore; D Richards a heretic washed-up piglet Shame pile. Happy Father's Day."

In 2016, Denise slapped Charlie with a $1.2 million lawsuit for allegedly evicting her and her children from a Beverly Hills estate and failing to provide promised financial support.

In response to the filing, Charlie's lawyer Martin Singer branded the lawsuit as "nothing more than money, money, money."

"Denise Richards is not satisfied that she has received $660,000 tax free each year for almost 10 years," the representative said in a statement. "It is not enough money for her, besides the approximate $10 million she has received from Charlie under her short marriage."

For the first time since their divorce, Charlie and Denise hit the red carpet together when they attended the Los Angeles premiere of the former's Netflix documentary, aka Charlie Sheen, on September 4.

Photos from the red carpet event showed the ex-couple posing for photos and sharing a hug at one point.