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Charlie Sheen’s Marriage and Relationship History

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Updated April 10, 2024561.4K views13 items

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For the complete “scoreboard” of Charlie Sheen’s girlfriends, here is the updated list. All of the famous women who have dated Charlie Sheen, listed alphabetically with photos of each woman. On November 17th, 2015, Sheen announced to the world that he was HIV positive, prompting everyone to wonder who Charlie Sheen has had sex with. If you’re wondering, “Who has Charlie Sheen dated?” then you’ve come to the right place. This list features Charlie Sheen’s ex-girlfriends along with additional information about them, such as when they were born and what their profession is. These women come in all shapes and sizes, but what they all have in common is that they’re all women that Charlie Sheen has either dated or “canoodled” with.

People that have dated Sheen include Denise Richards and Robin Wright. This list answers the questions, “What are the names of Charlie Sheen’s ex-girlfriends?” and “Who has Charlie Sheen hooked up with?”

It’s not certain whether the people on this list are women that Charlie Sheen has had sex with, but it’s safe to assume that when two adults are dating that some action will inevitably occur. Who has Charlie Sheen slept with? We can’t say for sure but it’s most likely all the women on this list.

Photo:
- Metaweb
- GNU Free Documentation License

Scottine Ross

Scottine Ross

Photo:
- George Pimentel
- Getty Images

Charlie Sheen began dating former adult film actress, Scottine Ross, also known by her screen name Brett Rossi, in November 2013. The duo reportedly became familiar at an annual gathering hosted by Sheen and soon fell for each other. Their whirlwind romance saw an engagement in February 2014, with Sheen referring to Scottine as his soulmate. Nonetheless, the relationship came to an end in October 2014, less than a month before their supposed wedding date, with Sheen attributing the decision to his intense desire to focus on his children.

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Capri Anderson

Photo:
- Ida Mae Astute
- Getty Images

Sheen’s short-lived relationship with adult film star, Capri Anderson, came to light in the public eye following a scandalous incident in a New York hotel in 2010. Their relationship was seemingly lead by high-intensity encounters and they were not publicly acknowledged as a couple per se. The duo reportedly met through a mutual acquaintance and Anderson was later hired as an escort for Sheen on the ill-fated night when he was found intoxicated and causing damage to his hotel room.

Age: 36
Birthplace: New York City, USA, New York
Brooke Mueller

Photo:
- Steve Granitz
- Getty Images

Charlie Sheen began dating real estate investor, Brooke Mueller, in 2006, shortly after his divorce with Denise Richards. The two were introduced through mutual friends and began a serious relationship. After two years of dating, they tied the knot in May 2008, with Mueller becoming Sheen’s third wife.

Together they had twin sons. But the marital bliss was short-lived, and Mueller filed for divorce in 2010, following a violent Christmas showdown in 2009. Their divorce was finalized in 2011, after struggling with custody disputes and battling Sheen’s public mishaps.

Age: 47
Birthplace: USA, Albany, New York
Denise Richards

Photo:
- Robert Mora
- Getty Images

Denise Richards and Charlie Sheen’s romance blossomed while filming for the movie Good Advice in 2000. They began dating shortly after, leading to their marriage in June 2002. From their union, they had two daughters.

However, their marriage was tumultuous and filled with allegations of abuse which led Richards to file for divorce in 2005 while pregnant with their second child. They finalized their divorce in November 2006, but have been on and off in their relationship, until finally ending up as friends for the sake of their children.

Age: 53
Birthplace: Downers Grove, Illinois, USA
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Brittany Ashland

Brittany Ashland

Photo:
- Axel Koester
- Getty Images

In 1990, Sheen began an affair with actress Brittany Ashland. The two met through industry connections and appeared to have a swift, heated fling. However, their relationship infamously ended in 1996 after Sheen was accused of assaulting Ashland during an argument. Despite a relatively short-lived and tumultuous relationship, the headline-making incident between the two made a lasting impact on public perception of Sheen’s personal life.

Donna Peele

Photo:
- Darlene Hammond
- Getty Images

Charlie Sheen’s first wife, Donna Peele, was a model he met during the filming of a cigarette commercial in 1995. Their whirlwind romance led to the couple getting married later that same year in September. However, their happily married life was short-lived when, barely six months after their wedding, Sheen filed for divorce. The divorce was officially granted in November 1996, just over a year from their wedding day, citing irreconcilable differences.

Tamara Beckwith
- Photo:
  - J. Vespa
  - Getty Images

Charlie Sheen dated Tamara Beckwith in 1995, an English television presenter. They met at one of Hollywood’s bash, where Sheen got smitten by her charismatic personality. Their relationship, however, was of ephemeral nature which lasted only for a few months. The couple didn’t publicly disclose the reasons for their split, thus it remains unspecified in the public domain.

Age: 54
Birthplace: England
Tracy Richman
- Photo:
  - Enter with Caution

In the late 1980s, Charlie Sheen started dating Tracy Richman, a television personality. Sheen and Richman met during a popular talk show filming where she was one of the guest. They hit it off immediately, but their relationship endured a hardly a year. The exact reasons for their break-up remains concealed but it is alleged that Sheen’s self-destructive patterns led to their separation.

Kelly Preston
- Photo:
  - Frank Trapper
  - Getty Images

Charlie Sheen got engaged to Kelly Preston, an American actress, in 1990. The couple met on the sets of an action comedy movie where they co-starred. Their engagement broke off within a year after a gun accidentally fired in their home which hit Preston in the arm. Sheen later admitted that he was responsible for the accident that subsequently caused the end of their relationship.

Age: Dec. at 57 (1962-2020)
Birthplace: Honolulu, Hawaii, USA
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Heidi Fleiss
- Photo:
  - Cindy Ord
  - Getty Images

In the mid-90s, Sheen was involved with Heidi Fleiss, an American former madam. Their relationship started off on a controversial note as Fleiss was known for running a high-profile prostitution ring. Fleiss’s legal troubles worsened during their relationship, which lasted about a year. Sheen ended their relationship once Fleiss’s illegal activities were made public.

Age: 59
Birthplace: Los Angeles, USA, Los Feliz, California
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