Bree Olson & Charlie Sheen: What You Should Know About Their Relationship


Bree Olson has been speaking out about her relationship with Charlie Sheen ever since the Anger Management star revealed on Tuesday morning’s Today show that he’s HIV-positive.

Here’s what you should know about Bree Olson and Charlie Sheen’s infamous relationship. The former adult film star was one of Sheen’s many “goddesses” at his Sherman Oaks mansion with his other “goddess” Natalie Kenly. During that turbulent time in Sheen’s life, he coined the phrases “winning” and “tiger blood.” Both Olson and Kenly joined him on his 2011 comedy tour, which was quickly cancelled after his downward spiral.

Bree Olson
(Photo by Ethan Miller/Getty Images)

Although their threesome looked wild and sexy in front of the cameras, it was anything but. Back in July 2011, Bree admitted to ABC News that life behind the cameras wasn’t as fun as it seemed because of Natalie’s close relationship to the actor.

“It was like you could cut the air with a knife sometimes. I felt like I couldn’t show Charlie the affection I wanted to show him, because of how she would react.”

During her latest interview with Inside Edition, Olson, whose real name is Rachel Oberlin, says that she took note of his HIV symptoms when she lived with him. It was reported via the Inquisitr that Charlie Sheen’s rep slammed Olson’s previous interview with Inside Edition, claiming that the comedian had several HIV tests taking during their relationship, all of which came back with negative results. Now Olson is firing back at Sheen’s reps during her second interview with Inside Edition.

“He and his managers want to treat me like I was just another ‘unsavory woman,'” she said to Inside Edition‘s Megan Alexander.

Bree says she believes that Charlie was diagnosed with HIV at the time of their controversial relationship. Charlie told Matt Lauer on the Today show that he did not find out about his HIV diagnosis until well after their relationship ended. But with good reason, Bree doesn’t believe the actor.

“It would give me peace of mind for Charlie to say a date [he found out]. That interview was so wishy-washy.”

Then Alexander asked Olson if she noticed any of Sheen’s symptoms at the time. The former Two and a Half Men star stated that he suffered from cluster headaches and night sweats. Olson responded, “Yes! Sweating all the time. He would keep the house in ridiculously cold temperatures.”

Bree Olson first appeared on the Howard Stern Show on Tuesday morning, around the same time that Charlie Sheen revealed on national TV that he is HIV-positive. Bree told the shock jock that Charlie never disclosed his medical status.

“He never said anything to me. I was his girlfriend, I lived with him. We were together. We had sex almost every day for a year with lambskin condoms, which do not protect…There were times we didn’t even use condoms, because it was only to prevent pregnancy. We were sleeping together every single night. He never said anything ever. ‘I’m clean,’ he said. I hesitated, and I made the same mistake that a lot of people do. I trusted him.”

Olson then decided to get another HIV test, which she found out was negative. She brought the test with her, which the host read on air that “no HIV antibodies were detected.” Olson even told Stern that she remembered the HIV symptoms that Sheen described in his Today show interview, but she shrugged them off.

While she’s obviously upset over the news of Charlie Sheen’s HIV diagnosis, his other ex-goddess, Natalie Kenly, is defending him in her latest interview with People magazine.

“He is not a monster. He’s a good man and I feel very fortunate to have spent time with him that I did. I’m so sad to hear of his health troubles.”

Olson revealed to Inside Edition that she’s surprised to hear of Kenly’s reaction. She believes that all of Sheen’s former lovers and ex-girlfriends need to stick together in this troubling situation. Before being linked to Olson and Kenly, Sheen was previously married to Brooke Mueller and Denise Richards. Both Mueller and Richards have tested negative for the virus, along with their children.

Bree Olson
(Photo by Ethan Miller/Getty Images)

Bree Olson grew up in Fort Wayne, Indiana. By the age of 19, she was a pre-med student. But by 24, she decided to become an adult film star. Olson went on to star in over 280 movies, some of which caught Sheen’s eye. She also made her mark as a former Penthouse Pet and Playboy model.

(Photos by Ethan Miller/Getty Images and Frederick M. Brown/Getty Images)

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