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
    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: 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

    more ABOUT
    • Age: age 44
    • Birthplace: USA, Downers Grove, Illinois
    • Profession: Television producer, Model, Actor
    • Credits: Starship Troopers, Love Actually, Scary Movie 3, The World Is Not Enough, Wild Things, + more
  3. 3

    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: age 53
    • Birthplace: Honolulu, Hawaii, USA
    • Profession: Model, Actor
    • Credits: Jerry Maguire, From Dusk till Dawn, Battlefield Earth, Sky High, Christine, + more
  4. 4

    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

    more ABOUT
    • Age: age 49
    • Birthplace: Texas, USA, Dallas
    • Profession: Spokesperson, Businessperson, Film Producer, Model, Actor, + more
    • Credits: Forrest Gump, The Princess Bride, House of Cards, Unbreakable, The Girl with the Dragon Tattoo, + more
  5. 5

    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
    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

    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

    more ABOUT
    • Age: 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

    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

    more ABOUT
    • Age: age 44
    • Birthplace: USA, Minnesota
    • Profession: Actor, Voice acting
    • Credits: Star Trek, Edward Scissorhands, Beetlejuice, Bram Stoker's Dracula, Being John Malkovich, + more
  9. 9

    Sheen and Lewis dated from 1986 to 1988. Lewis, a British actress who had just starred in Roman Polanski's Pirates when she met Sheen, was only 19 when the two got together. She later appeared in Playboy in 1993.

    Lewis said Sheen “was like a child when he made love, sweet and sensitive and very anxious to please. But after a while he began arriving home late. His brother had told me Charlie was an alcoholic, but I didn’t believe it."

    Charlotte Lewis is an English actress.more

    more ABOUT
    • Age: age 48
    • Birthplace: Kensington, London, United Kingdom
    • Profession: Actor
    • Credits: The Golden Child, Embrace of the Vampire, Pirates, Storyville, Excessive Force, + more
  10. 10

    Scottine Ross

    Sheen and former adult actress Scottine Ross got engaged in February of 2014, but broke up a few weeks before their wedding. Ross won a $5 million lawsuit against Sheen in 2015. Leaked home movies showed Ross sobbing as she claimed that Sheen abused her, made her get rid of a baby, and exposed her to HIV.

  11. 11
    Cathy St. George
    Photo: Freebase/CC-BY

    Sheen dated "adult" star and August 1982 Playmate of the Month Cathy St. George from 1988 to 1989.

    Cathy St. George is an actress.more

    more ABOUT
    • Age: age 61
    • Birthplace: Virginia, United States of America
    • Profession: Nude Glamour Model, Actor, Makeup Artist
    • Credits: The Man Who Loved Women, Grave Danger
  12. 12

    Domonique Simon was one of the most popular African American porn actresses of the 1990s.

    Domonique Simone is an African-American adult actress. At the age of 17, Simone won a scholarship to the Fashion Institute of Design and Merchandising. At the age of 18, in 1989, she answered an ad for figure modeling and soon found herself shooting for pornographic magazines like Hustler and ...more

    more ABOUT
    • Age: age 44
    • Birthplace: Georgia, USA, Valdosta
    • Profession: Pornographic actor
    • Credits: Edward Penishands
  13. 13

    Sheen dated porn actress Ginger Lynn on and off between 1990 and 1996. They ultimately split up because she claimed that his drinking was out of control.

    Ginger Lynn is an American pornographic model who came to prominence in 1980s videos. She also had minor roles in various B-movies. AVN has ranked her at #7 in a list of the 50 greatest porn stars of all time. After ending her adult-entertainment career she began using her full name of Ginger Lynn Allen ...more

    more ABOUT
    • Age: age 53
    • Birthplace: USA, Rockford, Illinois
    • Profession: Pornographic actor, Film Producer, Screenwriter, Actor, Film Director
    • Credits: The Devil's Rejects, American Pie Presents: Band Camp, Evil Breed: The Legend of Samhain, Vice Academy 3, Vice Academy, + more
  14. 14

    Sheen dated adult film star Heather Hunter briefly in 1994. She was inducted into the AVN Hall of Fame in 2003.

    Heather Keisha Hunter is an American former pornographic actress, who is now a rap artist, painter, and author.more

    more ABOUT
    • Age: age 46
    • Birthplace: New York City, USA, New York
    • Profession: Pornographic actor, Painter, Rapper, Author
    • Credits: He Got Game, Frankenhooker, Heather Hunter on Fire, Heat, The Black Ninja, + more
  15. 15

    Charlie Sheen dated Summer Altice from 1999-2000. She was named Playmate of the Month for August 2000.

    Summer Danielle Altice is an American fashion model and actress. She was named after Miss USA 1975, Summer Bartholomew.more

    more ABOUT
    • Age: age 36
    • Birthplace: USA, California, Fountain Valley
    • Profession: Nude Glamour Model, Model, Actor
    • Credits: Wedding Crashers, The Scorpion King, Grind, You, Me and Dupree, + more
  16. 16

    Charlie Sheen briefly dated British socialite Tamara Beckwith before she went on to date Sharon Stone's brother.

    Tamara Beckwith is an English celebrity, TV star, and gallerist.more

    more ABOUT
    • Age: age 45
    • Birthplace: England
    • Profession: Socialite, Actor, Presenter
    • Credits: Watchdog, Four Rooms, Casting Couch, I'm Famous and Frightened!, CelebAir
  17. 17

    Sheen dated adult film star Tabitha Stevens in 1990s.

    Tabitha Stevens is the stage name for an American pornographic actress. In 2007 she was inducted into the AVN Hall of Fame.more

    more ABOUT
    • Age: age 45
    • Birthplace: Long Island, New York, United States of America
    • Profession: Pornographic actor, Film Producer
    • Credits: Shade, Howard Stern on Demand, X-treme Tabitha, The Big Rock, Trashy, + more
  18. 18

    Socialite Tracy Richman dated Charlie Sheen in the late '80s and early '90s.

    TV personality, she has dated Charlie Sheen and Frank Stallone. She is a dedicated activist in raising awareness on health, politics, and news. Tracy has a 6 year old daughter with John Morrissey named Chloe.more

  19. 19

    Sheen dated both Olson and Kenly at the same time in 2011, referring to the adult film stars as his "goddesses." After Sheen's announcement of HIV positive status, Olson told news outlets that Sheen had not disclosed his status to her, and that the two had had unprotected sex.

    Rachel Marie Oberlin, best known by her stage name Bree Olson, is an American pornographic actress and Penthouse Pet. She performed in over 280 adult films from 2006 to 2011.more

    more ABOUT
    • Age: age 29
    • Birthplace: Texas, USA, Houston
    • Profession: Pornographic actor, Nude Glamour Model, Actor
    • Credits: The Human Centipede 3 (Final Sequence), Teenage Wasteland, Jesse Jane: Lust, Young as They Cum 21, Chicks Gone Wild 3, + more
  20. 20

    In 2010, Sheen made news for drunkenly trashing a hotel room while a woman was locked inside the bathroom. That woman was adult firm star Capri Anderson.

    Capri Anderson is a pornographic actress.more

    more ABOUT
    • Age: age 27
    • Birthplace: New York City, USA, New York
    • Profession: Pornographic actor
    • Credits: Accolades received by Spider-Man XXX: A Porn Parody, Criminal Desires
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