Charlie Sheen's wives and girlfriends — a journey through his relationship history
My romantic life is as uneventful as it possibly could be. It’s been that way for a long time.
Charlie Sheen spoke about his love life in an interview with People. He is one of Hollywood’s most talked-about actors, known as much for his turbulent personal life as for his successful acting career. Sheen has been married three times, to Donna Peele, Denise Richards, and Brooke Mueller, and has also been romantically linked to several women, including Kelly Preston, Robin Wright, and Georgia Jones.
Source: Getty Images
TABLE OF CONTENTS
Key takeaways
- Besides Charlie Sheen's three marriages, the actor has had several other relationships with high-profile women in the entertainment industry, including Kelly Preston, Robin Wright, Georgia Jones, Brett Rossi, Heather Locklear, and Amanda Bruce.
- He is a father of five children born from relationships with three different women. His children are Cassandra Estevez, Sam, Lola, Bob, and Max.
- Currently, the actor is not married and is not dating anyone. However, he has expressed a willingness to be in a relationship, but is not ready for marriage.
Profile summary
Full name | Carlos Irwin Estévez |
Nickname | Charlie Sheen |
Gender | Male |
Date of birth | 3 September 1965 |
Age | 60 years old (as of January 2026) |
Zodiac sign | Virgo |
Place of birth | New York City, New York, United States |
Current residence | Los Angeles, California, United States |
Nationality | American |
Ethnicity | White |
Religion | Christianity |
Sexuality | Straight |
Height in feet | 5'10" |
Height in centimetres | 178 |
Weight in pounds | 185 |
Weight in kilograms | 84 |
Hair colour | Dark brown |
Eye colour | Brown |
Mother | Janet Templeton |
Father | Ramón Antonio Gerardo Estévez |
Siblings | 3 |
Relationship status | Single |
Children | 5 |
School | Santa Monica High School |
Profession | Actor, producer, author |
X (Twitter) |
Get to know Charlie Sheen’s wives: List of all his exes
Charlie Sheen has been married three times, with each relationship attracting significant public attention. His wives came from different professional backgrounds, including entertainment and fashion. The marriages unfolded at various stages of his Hollywood career, often under intense media scrutiny.
Donna Peele (1995–1996)
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Charlie Sheen’s first marriage was to Donna Peele, an American model he met during a cigarette commercial shoot. The couple married in September 1995, but their union lasted less than a year. They divorced in 1996, citing irreconcilable differences.
In an interview, Sheen revealed that before the divorce, a voice kept telling him that his marriage with the model would not work. The short-lived marriage marked the beginning of the actor’s highly scrutinised romantic life.
Denise Richards (2002–2006)
Source: UGC
Sheen married actress Denise Richards in June 2002 after meeting her on the set of Good Advice. Their relationship attracted massive media coverage, especially during Richards’ pregnancy with their second child. The couple shares two daughters, Sam and Lola.
Richards filed for divorce in 2005, and the process was finalised in 2006. Their split involved public allegations and custody disputes, making it one of Sheen’s most controversial relationships.
Brooke Mueller (2008–2011)
Source: UGC
In May 2008, Charlie Sheen married real estate investor Brooke Mueller. The couple welcomed twin sons, Bob and Max, in 2009. Legal troubles, substance abuse issues, and repeated separations plagued their marriage.
Mueller filed for divorce in 2010, and it was finalised in 2011. The custody of their twins later became a central issue, with Denise Richards temporarily gaining guardianship.
Charlie Sheen’s girlfriend history
Charlie Sheen has been romantically linked to several high-profile women over the years. Many of these relationships, which unfolded in the public eye during the height of his fame, did not culminate in marriage. While some were brief, others became headline-making stories. They highlight another side of his complex personal life.
Kelly Preston (1989–1990)
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Before his marriages, Sheen dated actress Kelly Preston, who later married John Travolta. The pair was engaged, but their relationship ended after a gun incident in which Preston was accidentally injured, a moment Sheen later described as deeply regrettable. Despite the breakup, both went on to have successful careers.
Robin Wright (1990–1991)
Charlie Sheen briefly dated actress Robin Wright in the early 1990s. At the time, Wright was emerging as a major Hollywood star. Their relationship remained relatively private compared to Sheen’s later romances.
Heather Locklear (1990–1991)
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Sheen was also romantically linked to Heather Locklear, his Spin City co-star. Their short relationship gained attention due to Locklear’s popularity on television during that era.
Natalie Kenly (2006–2007)
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Following his divorce from Denise Richards, Sheen dated Natalie Kenly, a former nanny to his children. The relationship drew criticism and media scrutiny due to its timing and circumstances, though Sheen defended his polyamorous relationship.
Amanda Bruce (2010)
Amanda Bruce is an American model and social media personality who reportedly dated Charlie Sheen in the mid-2010s. The relationship emerged after Sheen had begun stepping back from the highly publicised lifestyle that characterised his earlier years.
While their romance was relatively brief, Bruce was occasionally mentioned as one of the women Sheen dated during his post-television career phase. The relationship ended quietly, with both parties keeping details largely out of the public eye.
Brittany Ashland (2010)
Brittany Ashland is an American adult film actress who was briefly linked to Charlie Sheen in the early 2010s. Their relationship reportedly occurred during a period when Sheen’s personal life was under heavy media scrutiny following his exit from Two and a Half Men.
Unlike some of his other romances at the time, Ashland’s connection with Sheen remained relatively private and short-lived, but it received media attention after Ashland sued him for battery in 1997.
Bree Olson (2011)
Source: Getty Images
Bree Olson is one of Charlie Sheen’s most well-known former girlfriends. The adult film actress moved into Sheen’s Los Angeles home in 2011 and was publicly described by him as one of his “goddesses”, a term that became closely associated with that phase of his life.
Their relationship received widespread media attention due to its unconventional nature and Sheen’s outspoken interviews during that period. Olson later stated that the relationship ended within months, citing personal and emotional challenges, and she has since spoken openly about wanting distance from that chapter of her life.
Brett Rossi (2013–2014)
Brett Rossi, an American adult film actress, was one of Sheen’s most publicised girlfriends in the 2010s. The couple became engaged in 2014, but later called off the engagement. Their relationship ended amid legal disputes and accusations, which dominated entertainment headlines at the time.
Georgia Jones (2014)
Source: UGC
In 2014, Sheen dated adult film actress Georgia Jones, with whom he later admitted to unprotected intimacy during his HIV disclosure interview in 2015. This relationship became part of the broader conversation surrounding his health announcement.
FAQs
- How many wives has Charlie Sheen had? The actor has been married three times—to Donna Peele (1995–1996), Denise Richards (2002–2006), and Brooke Mueller (2008–2011).
- How many biological children does Charlie Sheen have? He has five biological children: one daughter, Cassandra Estevez, and four sons, Sam, Lola, Bob, and Max.
- Who is the love of Charlie Sheen's life? The actor has never publicly named one person as the definitive love of his life. In interviews, he has often suggested that his children hold that place above any romantic relationship.
- Who has custody of Charlie Sheen's twins now? The twins, Bob and Max, are under a shared custody arrangement, with their mother, Brooke Mueller, holding primary physical custody recently, while Charlie Sheen has visitation rights.
- Who was Charlie Sheen’s most famous wife? Denise Richards is widely regarded as his most renowned wife due to her successful acting career and their highly publicised marriage and divorce.
- Was Charlie Sheen engaged after his divorces? He was engaged to Kelly Preston in the early 1990s and later to Brett Rossi (Scottine Ross), though neither engagement resulted in marriage.
- Is Charlie Sheen currently married? He is not married. While he is open to love again, he maintains that he is not ready for marriage.
Charlie Sheen’s wives and girlfriends reflect a complex personal journey shaped by fame, success, and public scrutiny. From brief marriages to headline-making romances, his relationship history has remained a defining aspect of his public image. Today, Sheen appears focused on personal growth and his five children.
Legit.ng recently published Regina Hall’s partner history. The American actress has been on the acting scene, putting her life under scrutiny. Over the years, her romances have hit the headlines multiple times, as she has been linked to several men in the entertainment industry.
Some of the notable people in her relationship history include comedian Damon Wayans, actor Hill Harper, and rapper Common. While some of the relationships are confirmed, others remain a subject of speculation.
Proofreading by Kola Muhammed, copy editor at Legit.ng.
Source: Legit.ng
