Their whirlwind romance in the noughties ended in a sour divorce, but they are now back on civilised terms seemingly for the sake of their daughters.

And so cordial is Charlie Sheen and Denise Richards’ relationship these days, that the Two and a Half Men star even agreed to film for his ex-wife’s Bravo reality show, Denise Richards & Her Wild Things, which premiered in March.

Of her decision to get Charlie on board, actress Denise said, ‘He’s very much a part of our lives, and [the show] is about our life. And I said, “Let’s support our daughters. You support your daughters. Please film with us.” And he did, and I’m glad that he did that.’

But as Charlie relishes the newfound amicability after years of strain, sources say he has also been confronting reignited feelings for his ex, who is married to businessman Aaron Phypers.

Following a report that Charlie – who has also been married to Donna Peele and Brooke Mueller – considers Denise ‘the one that got away’, a source close to the Hollywood leading man says, ‘Charlie has always carried a torch for Denise. Even when things were at their worst between them, he’d be the first to admit that she’s the most naturally beautiful woman he’s ever been with. And now that they’re getting along so well, all those old feelings are creeping back in. He thinks she looks better than ever and always raves that she’s ageing phenomenally well.’

The source adds, ‘For what it’s worth, he always considered her to be his true love and the one who understood him the best. He would love another chance with her, but for now, it’s only a dream.’

Charlie and Denise’s roller-coaster journey began in 2000 when they met on the set of Good Advice. But it wasn’t until a year later that they went on their first date, and by the second, Denise knew Charlie was ‘the one’.

The pair had been dating just shy of three months when they got engaged in December 2001, and they wasted no time tying the knot as they held their nuptials in June the following year. The whirlwind nature of their romance continued when they started a family – after welcoming daughter Sami in March 2004, they announced their second pregnancy in December the same year. But the fairytale came crashing down when Denise, 54, filed for divorce from Charlie, 59, when she was six months pregnant, citing ‘irreconcilable differences’. The couple were reported to have given things another go after becoming parents to daughter Lola, in June 2005, but they ended up pushing forward with divorce proceedings, which were finalised in 2006.

Meanwhile, after a highly publicised battle with alcohol and substance abuse which resulted in several rehab stints, Charlie is believed to be seven years sober.

The dad of four – who has a daughter Cassandra, 40, with ex-girlfriend Paula Profit, as well as 16-year-old twins Bob and Max with third wife Brooke – told People in December 2023 that he has a ‘very consistent lifestyle now’ since curbing alcohol and drugs.

According to divorce court documents, Denise accused the actor – whose hedonistic lifestyle was also said to have seen him splash ‘$300-$400,000 a year’ on prostitutes in the 90’s – of ‘abusive and threatening behaviour’. The reality star allegedly felt she had to ‘stop the cycle of abuse towards me and our children and [Charlie’s] continued threats of violence and statements that he is going to kill me’. She also claimed that issues in their marriage first arose on their honeymoon, when Charlie, who at the time was in recovery and attending Alcoholics Anonymous, started gambling and taking Xanax – something he asked her to keep a secret, per the court documents.

More bad blood ensued, as the TV personality later claimed her ex-husband – who has
also had brushes with the law and revealed in 2015 that he was HIV-positive – displayed ‘inappropriate behaviour… and conduct’ including his ‘attraction to underage women and his sexual explicitness on the internet, including revealing his private parts’.

Charlie responded 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.’

But the pair eventually managed to overcome their custodial and financial battles (in 2016, Denise brought a $1.2 million lawsuit against Charlie for allegedly not providing promised support for Sami and Lola) to reach a place of civility. And while Denise – who also adopted a daughter Eloise as a single parent in 2011 – has been happily married to Aaron for six years, insiders say that her first husband would still drop everything for her.

The source reveals, ‘Denise and Charlie went through a lot of nasty stuff in earlier years, but they’re good friends now and are co-parenting peacefully. Denise is very loyal to Aaron, but she does seem to enjoy the constant attention from Charlie. Anytime she’s got a problem she needs help with, he is just a phone call away. He acknowledges that she’s married, and he won’t cross any lines, but it’s no secret that if the door ever cracked open, he’d be the first to walk through it.’

In 2023, Charlie reinforced not only the good terms that he and Denise are on, but that their daughters were of utmost priority.

He said, ‘We went through so much s**t together that I don’t think either one of us has any energy left to be divisive. The only thing that matters is the kids.’

The insider now adds, ‘At the moment, Charlie is playing it cool and claims he’s helping with Denise Richards & Her Wild Things because his daughters want to do it, and he’d do anything for them. But no one doubts that his crush on Denise is a big part of it – it gives him an excuse to spend time with her. You just have to see the way he looks at Denise to know that he’s still in love with her.’