Denise Richards and Charlie Sheen's Relationship Timeline

Mar. 15, 2025

Photo: Jon Kopaloff/FilmMagic

Denise RichardsandCharlie Sheen’s relationship and subsequent divorce was one of the most public in Hollywood history.

After meeting in 2000 and marrying in 2002, the couple welcomed their first child, daughterSam Sheen, in 2004. They announced theirsecond pregnancylater that year, but a few months before the birth, the actress filed for divorce. The exes continued to go through a series ofupsanddownsin the years that followed, especially when it came to theirfinancesandcustody agreement.

Both Richards and Sheen have sincereflected on their relationshipand how itimpacted their daughters. On an episode ofThe Real Housewives of Beverly Hills, Richardsshared, “I just feel like I f—ed up a lot with their dad. I don’t want them to look back at their childhood and remember [fights].”

From meeting on set to raising their children, here’s the complete timeline ofDenise Richardsand Charlie Sheen’s relationship.

2000: Denise Richards and Charlie Sheen meet on set

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The couple first met while filmingGood Advicein 2000, but it wasn’t until Richards guest-starred on Sheen’s seriesSpin Cityin 2001 that the two got serious.

October 4, 2001: Denise Richards and Charlie Sheen go on their first date

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For their first date, the pair hung out at Sheen’s condo to watch the San Francisco Giants game. “I made the first move kissing him,” the actress toldPEOPLE. “He was Mr. Polite, such a gentleman.”

December 26, 2001: Charlie Sheen proposes to Denise Richards

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Less than three months after their first date, Sheen popped the question while on vacation at a spa in Arizona.

Richards recalled toPEOPLE, “When he pulled a box out, I knew. I wanted to scream ‘Yes,’ but I wanted to hear all the words.”

“I just said, ‘Denise, will you marry me?’ " Sheen added. “Pretty straightforward.”

June 15, 2002: Denise Richards and Charlie Sheen tie the knot

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The couple said “I do” atSpin Citycreator Gary David Goldberg’s Brentwood, California estate in anoutdoor ceremonyon June 15, 2002. Attendees included Sheen’s fatherMartin Sheen,Angie Harmon,Heather Locklear,Richie SamboraandBrooke Shields.

September 2003: Charlie Sheen and Denise Richards are expecting their first child together

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The couple’spublicist announcedthat Sheen and Richards were pregnant with their first child in September 2003. The publicist also revealed that the actress was due early next spring.

March 9, 2004: Charlie Sheen and Denise Richards welcome their first child together

December 17, 2004: Denise Richards and Charlie Sheen announce their second pregnancy

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“They are incredibly thrilled and I couldn’t think of a better Christmas present for the both of them and for little Sam,” Richards' agent, Chuck James, toldPEOPLE.

March 2, 2005: Denise Richards files for divorce from Charlie Sheen

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While six months pregnant with their second child, Richardsfiled for divorcefrom her husband of nearly three years, citing “irreconcilable differences.”

June 1, 2005: Denise Richards and Charlie Sheen welcome their second daughter

Amid her divorce from Sheen, Richardsgave birthto daughter Lola Rose Sheen on June 1, 2005.

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

However, a friend of Richards told PEOPLE that the couple were not together. “He wanted to be there. And she agreed to it,” said the source. “But they’re not getting back together.”

August 22, 2005: Denise Richards and Charlie Sheen attempt reconciliation

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Weeks after welcoming their second child together, the parents were looking ata possible path to reconciliationdespite their impendingdivorce.

“Things are a whole lot better, and I think with that (comes) hope,” Sheen toldExtra. “We’re not ruling anything out.”

Richards also seemed open to reconciliation, according to a source who toldPEOPLE, “She never wanted to get divorced. She always hoped they could save their marriage.”

January 4, 2006: Charlie Sheen and Denise Richards move forward with their divorce

“I don’t think this relationship (between Richards and Sheen) is going to work,” a source close to the former couple also shared with PEOPLE.

May 12, 2006: Charlie Sheen and Denise Richards attempt to privately settle their divorce

In an attempt to be more amicable with each other, the former couple issueda joint statementregarding the status of their relationship after trying todivorcefor over a year.

“Denise and Charlie are working with the Courts to privately resolve their differences regarding their children,” the pair said. “They hope to resolve this matter outside of the public forum and will both continue to make every effort in this regard.”

November 30, 2006: Denise Richards and Charlie Sheen’s status as a married couple ends

Almost two years after the divorce paperwork was initiallyfiled, Sheen and Richards werelegally able to wed other peoplein November 2006. The divorce, however, was not formally complete as the final division of assets and custody agreement were still ongoing.

At the time, Richardswas datingguitaristRichie Zamboraand Sheen wasin a relationshipwithBrooke Mueller.

July 10, 2007: Charlie Sheen gets engaged to girlfriend Brooke Mueller

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PEOPLEconfirmed Sheen’s engagement to actress and real estate investor Mueller in July 2007. The couple were first linked in June 2006.

A few weeks prior to the engagement,PEOPLEreported that Richards and Mueller were spotted together. “Denise wants her to feel comfortable,” a friend of Richards told PEOPLE previously. “She put together a bag with toys for her and the girls (Lola and Sam) along with a card telling her she’s glad (Brooke) makes their father so happy.”

September 2007: Denise Richards accuses Charlie Sheen of “inappropriate behavior” in custody battle

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Richardslaunched accusationsagainst her ex-husband, asking the court to protect theirchildrenfrom Sheen and remove his overnightprivilegeswith them.

Sheen countered in a statement: “Clearly the mother of my children has no interest in responsible co-parenting when it comes to my relationship with our girls.”

May 30, 2008: Charlie Sheen marries Brooke Mueller

Sheen married Muelleron May 30, 2008, at a private estate in L.A. Richardsdid not attend the nuptials, but she did admit a month prior to the wedding that her daughters would be there.

In March 2009, the newlyweds gave birth to twin boys,Max and Bob. Sheen and Mueller, however, eventuallyfiled for divorcein November 2010.

May 3, 2013: Denise Richards steps in to care for Charlie Sheen’s sons

After Sheen and Mueller’s sons wereremovedfromMueller’s custodydue to her allegedly erratic behavior,Richards stepped into care for them temporarily.

June 21, 2015: Charlie Sheen attacks Denise Richards on Twitter

On Father’s Day,Sheen launcheda brutal Twitter attack against ex-wife Richards, calling her a “heretic washed-up piglet Shame pile” among other insults in a series of deleted tweets.

“Denise Richardsis a shake down piece of s— doosh phace & worse mom alive! A despicable charlatan who sux ISIs ass,” he wrote.

“I have paid that kaly-vinnik leaky diaper over 30 Mil and she calls me a DbD (dead beat dad),” he added a few hours later. “See u in court you evil terrorist sack of landfill rash.”

November 17, 2015: Charlie Sheen reveals his HIV-positive status and Denise Richards responds

During a bombshell interview, Sheen admitted on theTodayshow that he wasHIV-positive. While the news came as a surprise to many, Richards was already aware of his diagnosis before Sheen’sannouncement.

“She’s known Charlie was HIV-positive for a number of years,” a source toldPEOPLE.

“He was infected after they divorced, and they haven’t been intimate since,” the source added. “Neither she nor their daughters are HIV-positive.”

January 2016: Denise Richards sues Charlie Sheen for $1.2 million

Richards brought a$1.2 million lawsuitagainst her ex-husband for allegedly not providing promisedfinancial supportfor their two daughters.

“Denise Richardsis not satisfied that she has received $660,000 tax-free each year for almost 10 years,” Sheen’s attorney Martin Singer told PEOPLE in a statement. “It is not enough money for her, besides the approximate $10 million she has received from Charlie under her short marriage.”

The actress responded onTwitter, writing, “Marty Singer u being the trustee should support a mom fighting to keep it intact for the children. It’s their money, not mine or your client.”

December 2017: Denise Richards starts dating Aaron Phypers

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Richards began dating Aaron Phypers as early as December 2017, PEOPLE reported. Phypers was previously married toDesperate HousewivesstarNicollette Sheridan.

September 6, 2018: Denise Richards gets engaged to Aaron Phypers

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PEOPLE exclusivelyrevealed Richards and Phypers' engagement news in September 2018. A source told PEOPLE, “Aaron and Denise just got engaged and would love to be married sooner than later now that his divorce is finally in his past. The engagement has been a long time coming. He moved on from his past relationship a long time ago, and marrying Denise is a welcome new chapter for both of them in different but equally significant ways.”

September 8, 2018: Denise Richards invites Charlie Sheen to her wedding with Aaron Phypers

Denise Richards Instagram

Richards extended an invitation to her ex-husband when it came time to plan her September2018 weddingtoPhypers. Though Sheen did not end up attending the Malibu nuptials, Richardsexplained her reasoningduring a later episode ofTheReal Housewives of Beverly Hills, which featured footage of the special day.

“No matter what’s gone down with Charlie and I, I invite Charlie to anything having to do with the kids and I,” she said. “Even if he did bring a prostitute as his date, I wouldn’t care,” she joked. “It’s just, it is what it is.”

May 20, 2020: Denise Richards recalls filing for divorce from Charlie Sheen while pregnant

During an episode ofRHOBH, theWild Thingsactressrecalledwhat it was like filing for divorce from Sheen 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 during her 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,” she added.

September 2021: Denise Richards and Charlie Sheen’s daughter Sami alleges living in an “abusive household”

Charlie Sheen Instagram

Richards and Sheen’s eldest daughter Samimade allegationson TikTok about what it was like living with her mother, saying she had been “trapped in an abusive household” and was “insanely depressed” in 2020, but that things were looking up a year later after escaping the “hell house.”

Via his publicist Jeff Ballard,Sheensaid, “Sam is amazing. I love her and all my children unconditionally. We’re having a ball. GED here we come.”

In a February 2022appearanceon SiriusXM’sJeff LewisLive, Richards gave an update abouther relationshipwith Sami, who was stillliving with Sheenat the time.

“Honestly, I have a strained relationship with her,” she admitted. “It’s very difficult. I know we’ll get back to where we were eventually but right now, it is strained. Obviously, I would love for her to live with me. She lived with me all these years.”

“But I think it’s very difficult raising teenagers now and especially in Los Angeles when there’s access to everything. We didn’t grow up with Postmates and Uber where you have everything that you want,” she continued. “There are certain rules and I enforce them. And [at Sheen’s], there’s different rules at that house and that’s okay.”

June 2022: Denise Richards and Charlie Sheen battle over daughter Sami’s OnlyFans account

The former couple spoke out after Sami, whoturned 18in March 2022, created anOnlyFansaccount. Sheen toldE! Newsthat he does “not condone” his daughter’s decision. “But since I’m unable to prevent it, I urged her to keep it classy, creative and not sacrifice her integrity.”

He added, “She is 18 years old now and living with her mother. This did not occur under my roof.”

ButRichardsdidn’t agree entirely that it was because of their daughter’s location, tellingPEOPLEthe choice “wasn’t based on whose house she lives in.”

“All I can do as a parent is guide her and trust her judgment, but she makes her own choices,” she added.

Samialso spokeabout her decision in anInstagram Q&A, saying her mother is “extremely supportive” and that she will be using her platform to focus on body positivity. “Only thing that matters is making sure you’re comfortable with what you’re posting & remembering that all bodies are beautiful,” Sami shared.

August 2022: Denise Richards says she “covered” for Charlie Sheen with their daughters

Richardstalkedabout her life after her divorce from Sheen on the Dear Media podcast,Divorced Not Dead.

She admitted she struggled with the decision to file for divorce because she felt guilty about breaking up her family and how it would impact her daughters.

“I never wanted the girls to — and I don’t know, maybe I did them a disservice, there’s no handbook for this, especially when you’re in the public too, and you have to deal with all this crap — but I never wanted them to sense any discord between us because I didn’t want them to feel unsettled,” Richards said.

Richards also admitted she “covered” for Sheen with the kids in regards to hispublic drama.

“I did shelter them a lot, and then they started to get to an age where ‘so and so said this,’ and I lied my ass off and covered for him,” she revealed, later adding, “Now as they’re starting to get older, they’re more aware of more things. That’s why I say I don’t know if I did them a disservice when they were younger.”

June 15, 2023: Source says Sami Sheen’s OnlyFans account is “causing drama” between Denise Richards and Charlie Sheen

Frazer Harrison/Getty Images for Race to Erase MS; Sami Sheen/Instagram

Since creating an OnlyFans account, Sami has started publicly calling herself a “sex worker.” According to a source, this is “causing a lot of drama” in the family.

“[Richards] knows her daughter is not a sex worker. She’s just saying outrageous things,” the insider told PEOPLE. “She doesn’t even show any skin on OnlyFans. Sami has 4,000 followers. So, she’s making $80,000 a month doing almost nothing and barely showing anything. She’s just teasing the audience.”

While Richards is supportive of her daughter, Charlie is completely against Sami’s decision to be on the platform.

“This may be something that Sami is doing to bother her father,” the source added.

November 7, 2023: Denise Richards says she was “incredibly naive” to Charlie Sheen’s addiction struggles

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When Richards first met Sheen, he’d been sober for four years. The actress didn’t “reform the bad boy,” instead, she remembers being “incredibly naive” to Sheen’s struggle with addiction, and was convinced he wouldn’t relapse.

“I didn’t judge him for his past because I figured, well, his past made him who he is today,” Richards said onBethenny Frankel’sJust Bpodcast. “And the person that I met was very different from the person that spiraled. I wouldn’t have dated him if I met him when he was deep in addiction.”

February 19, 2025: Denise Richards says Charlie Sheen has been “supportive from day one”

While talking to PEOPLE in February 2025, Richards said that Sheen has been “supportive” of her from day one, and even sent her a “wonderful sweet positive text” after the trailer for her new reality series,Denise Richards & Her Wild Things, premiered.

“Charlie is always invited to holiday dinners,” she said. “There’s always an open door and that goes for Brooke and the boys as well. I’m always, the more the merrier. I want everyone to get along and everyone to be peaceful.”

source: people.com