Women Who Charlie Sheen Has Dated

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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.
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  1. 1
    Brooke Mueller is listed (or ranked) 1 on the list Women Who Charlie Sheen Has Dated
    Photo: Freebase/Public domain
    Sheen and real estate agent Brooke Mueller married in 2008 and welcomed twin sons a year later. But in December 2009, Sheen was arrested for domestic violence before both he and Mueller entered rehab for substance abuse. They tried to make it work for a few more months, before ultimately divorcing in late 2010.

    Brooke Jaye Mueller is an American actress. more

    more ABOUT
    • Age: 38
    • Birthplace: Albany, New York, United States of America
    • Profession: Real Estate Broker, Actor
    • Credits: A Love Song for Bobby Long, Witchouse, Strictly Sexual, The Possessed
  2. 2
    Sheen's tumultuous relationship with his second wife was tabloid fodder for years. The two married in 2002, and welcomed their daughter Sam in 2004. But when Richards was six months pregnant with their second daughter, Lola, in 2006, she filed for divorce and asked for a restraining order. Richards claimed that Sheen brought prostitutes to their home, gambled illegally, and created an unstable environment for their children.

    Denise Lee Richards is an American actress and former fashion model. She has appeared in films, including Starship Troopers, Wild Things, Drop Dead Gorgeous, The World Is Not Enough as a Bond girl, and in Valentine. She played Monica and Ross Geller's cousin on Friends. From 2008 to 2009, she starred on ...more

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    • Age: 44
    • Birthplace: Downers Grove, Illinois, United States of America
    • Profession: Television producer, Model, Actor
    • Credits: Starship Troopers, The World Is Not Enough, Wild Things, Valentine
  3. 3
    Kelly Preston is listed (or ranked) 3 on the list Women Who Charlie Sheen Has Dated
    Photo: Tinseltown/Shutterstock
    Before she went on to marry John Travolta, Kelly Preston was engaged to Charlie Sheen. The two got together after divorce from Kevin Gage in 1987. They stayed together until 1990, when Sheen accidentally shot (!) Preston in the arm with a loaded shot gun he had in his pocket.

    Kelly Preston is an American actress and former model. She has appeared in more than 60 television and film productions, most notably including Mischief, Twins and Jerry Maguire. She is married to John Travolta. more

    more ABOUT
    • Age: 53
    • Birthplace: Honolulu, Hawaii, USA
    • Profession: Model, Actor
    • Credits: Jerry Maguire, Twins, Death Sentence, For Love of the Game
  4. 4
    Robin Wright is listed (or ranked) 4 on the list Women Who Charlie Sheen Has Dated
    Photo: Freebase/CC-BY-SA
    Robin Wright was one of Charlie Sheen's first girlfriends. The two dated as teenagers from 1981 t0 1982, when they were both breaking into the business.

    Robin Gayle Wright is an American actress and television director. She was previously credited as Robin Wright Penn. Wright first gained attention when starring in the NBC soap opera Santa Barbara as Kelly Capwell from 1984 to 1988, for which she received three Daytime Emmy nominations. She made the ...more

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    • Age: 49
    • Birthplace: Texas, USA, Dallas
    • Profession: Spokesperson, Businessperson, Film Producer, Model, Actor, + more
    • Credits: The Princess Bride, Forrest Gump, House of Cards, Santa Barbara
  5. 5
    Brittany Ashland is listed (or ranked) 5 on the list Women Who Charlie Sheen Has Dated
    Photo: user uploaded image
    Sheen dated actress Brittany Ashland in the late '90s, but the couple's relationship ended violently in 1997. Sheen pleaded no contest to misdemeanor battery charges after grabbing Ashland by the hair and slamming her head into their marble floor during an argument at home. Ashland was hurt so badly that her split lip required seven stitches. Sheen was sentenced to a a one-year suspended prison term and two years probation.
  6. 6
    Donna Peele is listed (or ranked) 6 on the list Women Who Charlie Sheen Has Dated
    Photo: Freebase/Fair use
    Charlie Sheen's first marriage was to former model Donna Peele in 1995. He announced their engagement during ex-girlfriend Heidi Fleiss's trial. Peele and Sheen divorced a year later.

    Donna Peele is a model. more

    more ABOUT
    • Profession: Model
  7. 7
    Heidi Fleiss is listed (or ranked) 7 on the list Women Who Charlie Sheen Has Dated
    Photo: user uploaded image
    Sheen may have briefly dated the most famous madam in Hollywood history in 1988. He famously testified against her at her 1995 trial for tax evasion and pandering. He admitted to spending more than $50,000 on her prostitutes.

    Heidi Lynne Fleiss is an American former madam, and also a columnist and television personality regularly featured in the 1990s in American media. She ran a prostitution ring based in Los Angeles, California, and is often referred to as the "Hollywood Madam". more

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    • Age: 50
    • Birthplace: Los Feliz, Los Angeles, California, United States of America
    • Profession: Pimp, Journalist, Author, Actor, TV Personality
    • Credits: The Doom Generation, Celebrity Rehab with Dr. Drew, Celebrity Rehab Presents Sober House, Celebrity Big Brother, Porndogs: The Adventures of Sadie, + more
  8. 8
    Winona Ryder is listed (or ranked) 8 on the list Women Who Charlie Sheen Has Dated
    Photo: Andrea Raffin/Shutterstock
    Sheen and Ryder dated in the late '80s after starring together in the 1986 movie Lucas. Soon afterward, Ryder hit the big time with 1988's Heathers.

    Winona Ryder is an American actress. She made her film debut in the 1986 film Lucas. As Lydia Deetz, a goth teenager in Tim Burton's Beetlejuice, she won critical and popular recognition. After various appearances in film and on television, Ryder continued her acting career with the cult film Heathers, ...more

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    • Age: 44
    • Birthplace: Minnesota, United States of America
    • Profession: Actor, Voice acting
    • Credits: Edward Scissorhands, Black Swan, Girl, Interrupted, Dracula
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