Amid Revelations From New Netflix Doc, Here's What We Know About Charlie Sheen's Past Relationships

Actor Charlie Sheen is best known for a few things: Two and a Half Men, Red Dawn, Ferris Bueller's Day Off, and getting into trouble. The comedic actor went through a rough period in time where he was making the kinds of headlines no one wants to make, but he seems to be on a much better path these days.

In September 2025, he released a Netflix documentary called aka Charlie Sheen.

In the documentary, Charlie shared some revelations about his relationship history, including some things that many people did not expect. Here's a look back at his relationships and what he had to say that surprised some.

Charlie has been married three times. According to Parade, his first marriage was to Donna Peele, and it lasted from September 1995 to 1996. He stayed single for a few years and then got with a pretty recognizable name in Hollywood for his next marriage: Denise Richards.

Denise has an acting career of her own, with some of her biggest roles including Starship Troopers, Wild Things, and the James Bond film The World Is Not Enough. She also later starred in Real Housewives of Beverly Hills. Parade notes Denise and Charlie were married from 2002 to 2005. Denise filed for divorce, and the divorce was finalized in 2006.

After Denise, Charlie dated actor and real estate investor Brooke Mueller, known for her roles in Witchouse, Strictly Sexual, and starring alongside her bestie Paris Hilton in Paris's The World According to Paris.

They married in 2008, and he filed for divorce in 2010. It was finalized a few months later.

Revelations in aka Charlie Sheen have unearthed some history that some fans were not aware of. According to the actor, he had some sexual relationships with men back in the day, including when he was addicted to crack, a period in his life that he referred to as both "chaotic" and "liberating."

When speaking in the documentary about sharing his same-sex experiences, Charlie mused (via People) that it was "Liberating. It’s f--king liberating... [to] just talk about stuff. It’s like a train didn’t come through the side of the restaurant. A f--king piano didn’t fall out of the sky. No one ran into the room and shot me."

Charlie also explained that because the experiences came while he was using crack, he struggled to come to terms with what they might mean for him. He explained, "That's what started it. That's where it was born, or sparked. And in whatever chunks of time that I was off the pipe, trying to navigate that, trying to come to terms with it — 'Where did that come from?... Why did that happen?' — and then just finally being like, 'So what?' So what? Some of it was weird. A lot of it was f---ing fun, and life goes on."

It was during this period of time where he contracted HIV, which he says he can be sure he "never passed on" to any other partners. The revelations in Charlie's documentary may come as a surprise to some, but they also show that he's at a point where he's looking back and beginning to process some of the more chaotic periods of his life. Which may be thanks to a memoir he released called The Book of Sheen, diving in to some of the same topics as aka Charlie Sheen.