Real-Life Celebrity Breakup: Denise Richards and Charlie Sheen

Denise Richards and Charlie Sheen — despite a sweet, almost storybook beginning, this celebrity pairing crashed and burned something fierce. Over a decade later, the proverbial flames are still being stoked.

How Did Denise Richards and Charlie Sheen Meet?

Despite making each other’s acquaintance and cultivating a friendship during the production of the feature film Good Advice, Richards and Sheen didn’t foresee romantic possibilities until their paths crossed again a year later.

By that time, Richards had accepted the opportunity to appear in five episodes of political sitcom Spin City, a program on which Sheen starred. For their first date, the pair decamped to Sheen’s condo where they watched an October 4, 2000, World Series game.

“We had an awkward little moment by the door,” recalled Richards in her 2011 memoir Real Girl Next Door. “I thought, is he going to kiss me? Do I make a move first? Do we not kiss at all? When he hesitated, I thought, screw it. I’ll be bold and make the first move – and so I planted one on him. It was spectacular. Definitely butterflies.”

At the conclusion of date number two, Richards said, “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.”

For his part, Sheen was just as smitten. However, with one divorce already behind him, he looked to two slightly peculiar sources for approval of his budding relationship and his desire to take it to the next level — his Spin City co-star, Heather Locklear and his therapist of many years.

Luckily, both parties offered their blessing. In fact, according to Sheen, the latter, “totally co-signed it. He believes in love at first sight and the reality of knowing when you know.”

Wedding Bells
In December of 2001, a mere two months into their courtship, Sheen began collaborating with jewelry designer Barry Kagasoff on an engagement ring for Richards. The resulting bauble was a 4.3-carat solitaire diamond set atop three rows of 100 tinier diamonds. Locklear was the first outside of Sheen to gaze at its countenance.

On the day after Christmas, Sheen proposed to Richards. According to the future Two and Half Men actor, “I just said, ‘Denise will you marry me?’ Pretty straightforward.”

Subsequently, the traditional Roman Catholic service was held on June 15, 2002, inside a stately home owned by Spin City creator Gary David Goldberg. A six-person gospel choir serenaded the newly deemed Mr. and Mrs. with Take Me Out to the Ball Game and Oh, Happy Day, while the couple took to the dance floor and performed a routine choreographed by Fame alum Debbie Allen.

Happier Days and Bitter Parting 
During the next few years, all seemed well. Richards and Sheen played husband and wife in the horror film spoof Scary Movie 3, former lovers in Two and a Half Men, and welcomed a daughter, Sam J, on March 9, 2004.

However, come 2005, the end was nigh. In March of that year, while six months pregnant with her second daughter (Lola Rose), Richards filed a petition for divorce with Los Angeles Superior Court citing “irreconcilable differences” and requesting legal and physical custody of her children.

A reconciliation halted the proceedings, but only momentarily. By January of 2006, they filed legal papers that requested a private arbitrator to handle the divorce. The decree absolute was delivered on November 30.

No doubt a welcomed resolution to an ordeal that had seen Richards’s request (and be granted) a restraining order against Sheen. She claimed her ex had threatened to murder her and her family — and other allegations including mental instability on Sheen’s part with an addiction to gambling, alcohol, and “disturbing porn” contributing to it.

Denise Richards and Charlie Sheen – Post Divorce

Over the next 14 years, Richards and Sheen’s relationship oscillated between bitter recrimination and joyful co-parenting, dirty tricks, and friendly banter.

They worked together in both a Tyler Perry film and episodes of Sheen’s FX comedy series Anger Management but later argued over Sheen evicting Richards and their two daughters from a house that he had supposedly purchased for their use.

In 2015, Sheen took to Twitter and termed Richards, among other things, a “terrorist” and “worst mom alive.” A year later, Richards launched a lawsuit against him alleging that he had pilfered money from a trust fund set up for their children.

Speaking to People magazine in February of 2019, Richards said that she wouldn’t call her relationship with Sheen “a failure. It’s a journey. It went a different way than we anticipated, but that’s okay. And I will always be a good friend to him.” Seven months later, she filed a complaint alleging Sheen owed her $450,000 in unpaid child support.