Charlie Sheen and Denise Richards have shared two children and two decades of a relationship rockier than Sylvester Stallone’s entire career. But their children had ensured that the couple “tries” their best to stay sane together to raise their kids. Let’s take a look at their tremulous relationship timeline.
Charlie Sheen and Denise Richards are the epitome of a quintessential Hollywood “frenemy” couple. They met in the early 2000s, fell in love, did some successful projects together, divorced a few years later. And since then, there have been countless ups and downs in their relationship. However, while they still manage to co-parent their kids, there has been a very interesting timeline that their relationship has shared. So let’s get right into it.
Highlights —
- Charlie Sheen and Denise Richards married
- Charlie Sheen and Denise Richards still friends?
Believe it or not, Charlie Sheen was once the ultimate Hollywood heartthrob. With his bad-boy image, he was known as a quintessential ladies’ man. In 2000, his eyes fell upon a pretty lady going by the name of Denise Richards, who was starring alongside him in the show ‘Good Advice’. While the romance did not begin immediately, there was an initial spark between the two.
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Charlie Sheen and Denise Richards’ relationship timeline
Fast forward to a year and Denise was starring in the television series titled ‘Spin City’, wherein she was playing a supporting role. Charlie, meanwhile, was signed to play a guest role for a single episode. And when they both met again, it was when they couldn’t resist getting attracted to each other and began dating. Their fairytale romance seemed too good to be true because it took them about a year to decide that they wanted to spend their lives with each other. They married in June 2002 with the hopes of having found each others’ soulmates. A year later, Denise announced that she was pregnant, during the premiere of the film ‘Scary Movie 3’, in which they starred together. All good and cheerful!

But hold your horses. Only if love stories were this perfect in real life! Shortly after they starred together in ‘Two and a Half-Men’, Charlie’s biggest claim to fame, their marriage, began showing red flags. In 2005, Denise filed for divorce, when she was pregnant with their second child. It was a major blow for the couple’s fans who weren’t ready to take a blow this hard. A ray of hope emerged between the two when their daughter was born in 2006 as the couple seemed to have reconciled. But it wasn’t for long and soon after the news of reconciliation erupted, it was followed by the heartbreaking news that the celebrity power couple was going ahead with the divorce.
“But what was the reason?” the fans asked. Well, it seemed that the bad boy image Charlie had, loomed like an ominous shadow over his head. Denise accused him of medication abuse, violent mood swings, and gambling and porn addiction. Needless to say, it seemed like there was no way they could be together again and rightly so, the divorce was made official in April 2006. They decided to co-parent both their kids and for a few years after that, there was silence from both ends as they both got busy with their respective work and romantic involvements.
However, in 2012, the reports of Charlie and Denise going on a holiday together with their kids made headlines. While they discarded the rumours of being back together again, they did mention that they had reconciled and had become very good friends. It seemed that they had buried the hatchet for the good of their children. But the story did not end here. In fact, it was far from meeting an ending, especially a happy one!
Out of the blues, one fine day in 2015, Charlie took on Twitter and began ranting about how bad Denise was as a mother and much more! This received no response from Denise. Later that year, Charlie revealed his HIV status to the world and in the next year, Denise sued Charlie for sending obscene texts about Denise to their daughter. In the next few years, from Charlie not attending Denise’s marriage, to fighting a custody battle with her, their relationship saw a lot of drama.
Denise Richards and Charlie Sheen are finally friends?
Finally, in 2020, Denise said in an interview that everything was good between her and Charlie, hinting towards a platonic friendship.
Well, that’s way more turns and twists than a trashy 80s Hollywood spy thriller. We hope that all will be good between them. As we age, we mature! You listening, Charlie?
Tell us in the comments which celebrity couple has the most interesting relationship timeline other than Charlie and Denise? Also tell us if there is a little part of you that wants to see them together, again.
