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After meeting in 2000 and marrying in 2002, the couple welcomed their first child, daughter Sam Sheen, in 2004. They announced their second pregnancy later that year, but a few months before the birth, the actress filed for divorce. The exes continued to go through a series of ups and downs in the years that followed, especially when it came to their finances and custody agreement.
Both Richards and Sheen have since reflected on their relationship and how it impacted their daughters. On an episode of The Real Housewives of Beverly Hills, Richards shared, "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 of Denise Richards and Charlie Sheen's relationship.
2000: Denise Richards and Charlie Sheen meet on set
October 4, 2001: Denise Richards and Charlie Sheen go on their first date
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 told PEOPLE. "He was Mr. Polite, such a gentleman."
By their second date, Richards knew that he was "the one." She recalled, "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."
December 26, 2001: Charlie Sheen proposes to Denise Richards
Less than three months after their first date, Sheen popped the question while on vacation at a spa in Arizona.
Richards recalled to PEOPLE, "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
The couple said "I do" at Spin City creator Gary David Goldberg's Brentwood, California estate in an outdoor ceremony on June 15, 2002. Attendees included Sheen's father Martin Sheen, Angie Harmon, Heather Locklear, Richie Sambora and Brooke Shields.
September 2003: Charlie Sheen and Denise Richards are expecting their first child together
The couple's publicist announced that 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
Just a few months after welcoming their first child together, the couple announced that baby number two was on the way.
"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, told PEOPLE.
March 2, 2005: Denise Richards files for divorce from Charlie Sheen
"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," Sheen's rep told PEOPLE in a statement.
June 1, 2005: Denise Richards and Charlie Sheen welcome their second daughter
Amid her divorce from Sheen, Richards gave birth to 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
"Things are a whole lot better, and I think with that (comes) hope," Sheen told Extra. "We're not ruling anything out."
Richards also seemed open to reconciliation, according to a source who told PEOPLE, "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
"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 initially filed, Sheen and Richards were legally able to wed other people in November 2006. The divorce, however, was not formally complete as the final division of assets and custody agreement were still ongoing.
July 10, 2007: Charlie Sheen gets engaged to girlfriend Brooke Mueller
PEOPLE confirmed 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, PEOPLE reported 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
In legal documents obtained by Access Hollywood, Richards claimed the Two and a Half Men star exhibited "inappropriate behavior ... and conduct," including "his attraction to underage women and his sexual explicitness on the internet, including revealing his private parts."
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
May 3, 2013: Denise Richards steps in to care for Charlie Sheen's sons
June 21, 2015: Charlie Sheen attacks Denise Richards on Twitter
On Father's Day, Sheen launched a 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 Richards is 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 the Today show that he was HIV-positive. While the news came as a surprise to many, Richards was already aware of his diagnosis before Sheen's announcement.
"She's known Charlie was HIV-positive for a number of years," a source told PEOPLE.
"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
According to legal documents filed by the actress, Sheen allegedly evicted Richards and their children from a house he owned that was adjacent to his home in Beverly Hills. The filed documents also alleged that Sheen did not provide money for Richards and their daughters to purchase a new home as he had promised.
"Denise Richards is 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 on Twitter, 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
Richards began dating Aaron Phypers as early as December 2017, PEOPLE reported. Phypers was previously married to Desperate Housewives star Nicollette Sheridan.
September 6, 2018: Denise Richards gets engaged to Aaron Phypers
PEOPLE exclusively revealed 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
Richards extended an invitation to her ex-husband when it came time to plan her September 2018 wedding to Phypers. Though Sheen did not end up attending the Malibu nuptials, Richards explained her reasoning during a later episode of The Real 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
"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"
Richards and Sheen's eldest daughter Sami made allegations on 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."
"Charlie didn't support implementing Denise's rules. He has a different way of parenting and Sami decided to live with her dad," a source told PEOPLE. "Denise loves her daughter very much and she's saddened by the situation."
Via his publicist Jeff Ballard, Sheen said, "Sam is amazing. I love her and all my children unconditionally. We're having a ball. GED here we come."
"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, who turned 18 in March 2022, created an OnlyFans account. Sheen told E! News that 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."
"All I can do as a parent is guide her and trust her judgment, but she makes her own choices," she added.
Sami also spoke about her decision in an Instagram 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.
Following the controversy, Richards made her own OnlyFans account and issued a lengthy statement, writing, "I have to say, I wish I had the confidence my 18 yr old daughter has. And I also can't be judgmental of her choices."
August 2022: Denise Richards says she "covered" for Charlie Sheen with their daughters
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 his public 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
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
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 on Bethenny Frankel's Just B podcast. "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."
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