A Look at Charlie Sheen and Denise Richards’ Explosive Relationship… From Disturbing Allegations to Online Insults and More

Charlie Sheen and Denise Richards connected 25 years ago, but the couple’s relationship has gone through dark days.

RadarOnline.com can reveal details about the Hollywood’s pair’s rollercoaster journey.

The two 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 that 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 writes. “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 adds: “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.”

Their first daughter, Sami, 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 Sheen, 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, Richards 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,” Richards 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, Sheen and Richards expanded their family when they welcomed their second child, Lola.

“We’re thrilled to finally meet our beautiful daughter,” they said in a statement.

Sheen also shares daughter Cassandra Jade Estevez with his high school girlfriend Paula Profit and twins, Bob and Max, 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 Richards 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 Richards “never wanted to get divorced” and “always hoped they could save their marriage.”

Sheen and Richards’ efforts to save their marriage appeared to have failed as they moved forward with their divorce.

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

“Denise and Charlie are working with the Courts to privately 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.

On Father’s Day in 2015, Sheen called out Richards 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–.”

Sheen then compared Richards to Mueller in a second tweet: “Brooke M is a sexy star whom I adore; D Richards a heretic washed-up piglet Shame pile. Happy Father’s Day.”

In 2016, Richards slapped Sheen with a $1.2million 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 $10million she has received from Charlie under her short marriage.”

For the first time since their divorce, Sheen and Richards 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.