Inside Charlie Sheen's Love Life, 4 Yrs Marriage With Denise Richards To Most High-Profile Romances

Charlie Sheen, born Carlos Irwin Estévez, is a well-known American actor whose career spans decades in both film and television. He first rose to fame in the 1980s with roles in hit films like Platoon (1986), Wall Street (1987), and Major League (1989). Charlie later became a household name for his comedic roles, most notably as 'Charlie Harper' in the long-running CBS sitcom Two and a Half Men and later in Anger Management.

While Charlie's acting talent earned him awards and acclaim, his personal life has often overshadowed his career. Known for his 'bad boy' persona, Charlie has been making headlines in tabloids for everything from addiction struggles and legal issues to a long list of relationships with actresses, models, and adult film stars. Let's have a closer look at his illustrious dating life.

Charlie Sheen had a daughter with his high school girlfriend

Way before Charlie became a Hollywood superstar, he was a boy in high school dating a girl who has been identified as Paula Profit. Little is known about this relationship to the world; some even claim her name to be Paula Speert. The two were high school sweethearts, and while their relationship did not last, they share a daughter, Cassandra Estevez. From his daughter, Charlie has one granddaughter, named Luna.

Charlie Sheen's early relationships in Hollywood

Before either was a household name, Charlie briefly dated actress, Robin Wright. They met at a celebrity event and dated for about a year. Their split was due to personal differences and career focus. At this time, he was linked with many other celebrities and high-profile women. Charlie also had a brief romance with Winona Ryder. Though they had strong chemistry, they parted ways amicably to focus on their individual acting paths.

British actress, Charlotte Lewis dated Charlie during the late '80s when she was just starting her film career. She later described him as sweet but immature in intimate relationships. The romance fizzled after a couple of months. TV personality, Tracy Richman had a brief relationship with Charlie in the late '80s. Though little is known about their split, it is rumoured that Sheen's self-destructive behaviour was a contributing factor.

Charlie Sheen was engaged to Kelly Preston 

In January 1990, Charlie Sheen was engaged to actress, Kelly Preston. However, their engagement ended abruptly after a firearm accidentally discharged in their home, sending shrapnel that injured Kelly. The incident, which drew significant media attention, led Kelly to call off their engagement shortly afterwards. Charlie later admitted he was responsible for the accident.

Following the breakup, Charlie entered a period marked by high-profile and controversial relationships, notably dating several adult film stars throughout the 1990s, including Ginger Lynn and Heather Hunter. This era further solidified Charlie's reputation for living life on the edge, both professionally and personally.

By the mid-1990s, Sheen's relationship with Heidi Fleiss, a notorious Hollywood madam, added more fuel to his already controversial image. Once Heidi's legal issues came to light, Sheen distanced himself from the relationship. English television presenter, Tamara Beckwith dated Charlie briefly in 1995. Their fling lasted only a few months and ended quietly, with neither party revealing much about the split.

Charlie Sheen's first marriage to Donna Peele 

Charlie Sheen's first marriage was to model, Donna Peele, whom he met during a commercial shoot. Their whirlwind romance led to a September 1995 wedding, but their marriage lasted less than a year. That same year, Charlie was named as one of the clients of an escort agency operated by Heidi Fleiss; speculations believed this to be the reason for the couple's divorce. However, Charlie cited irreconcilable differences, and the union quickly ended amid his growing personal controversies. 

Charlie Sheen's short-lived romance with Brittany Ashland 

Actress Brittany Ashland had a short but dramatic relationship with Charlie in 1996-1997. The relationship ended in controversy when she accused him of assault, leading to Charlie pleading no contest to battery charges. The incident once again reinforced his troubled public persona.

Charlie Sheen's marriage to Denise Richards 

Charlie Sheen met actress, Denise Richards on the set of Good Advice in 2000, and their connection quickly deepened. They began dating in October 2001 after Richards guest-starred on Spin City, and were engaged by December of that year. The couple married on June 15, 2002, at the estate of Spin City creator Gary David Goldberg. Together, they welcomed two daughters, Sami (born 2004) and Lola (born 2005). However, their marriage unravelled dramatically. 

In March 2005, while pregnant with their second child, Denise filed for divorce, alleging drug and alcohol abuse, threats of violence, and deeply disturbing behaviour, including claims about Charlie's alleged interest in inappropriate content. Charlie denied the accusations and stated that the FBI had investigated and cleared him of any wrongdoing. 

Charlie and Denise's divorce was finalised in November 2006, followed by a bitter custody battle. Despite years of conflict, the two have made efforts in recent years to improve their co-parenting relationship for the sake of their daughters. The two have been spotted in public together recently at a red carpet event for the Netflix documentary, Charlie Sheen.

Charlie Sheen's marriage to Brooke Mueller 

Real estate investor, Brooke Mueller, became Sheen's third wife in 2008. They welcomed twin sons, Bob and Max, in 2009. Their relationship unravelled after Charlie was arrested for domestic violence in 2009. Brooke filed for divorce in 2010, which was finalised in 2011. Since then, they've shared a tumultuous co-parenting journey, with Denise Richards temporarily taking care of their twins during Brook's rehab stints.

Charlie Sheen and his relationships after his third divorce

Adult film actress, Capri Anderson and Charlie Sheen made headlines after a chaotic night in a New York hotel in 2010. She was reportedly hired as an escort, and the night ended with police intervention. Capri later filed legal claims against Charlie.

In March 2011, Charlie started living with 24-year-old adult film actress, Bree Olson and 24-year-old model and graphic designer, Natalie Kenly, whom he collectively nicknamed his 'goddesses'. Bree left Charlie in April 2011, and shortly after, Natalie went in June 2011. In a January 2013 interview on Piers Morgan Tonight, Charlie stated that he was in a relationship with adult film actress and 2011 Penthouse magazine Pet of the Month, Georgia Jones.

Charlie Sheen's engagement to Scottine Ross a.k.a Brett Rossi 

Former adult film actress Scottine Ross, known as Brett Rossi, was engaged to Charlie in 2014. The engagement ended months before their planned wedding. Scottine later filed a lawsuit against Charlie, citing emotional distress and allegations involving his undisclosed HIV status.

Where is Charlie Sheen today

Today, Charlie Sheen is a father of five and a grandfather. He maintains joint custody of his twins, Bob and Max, with Brooke Mueller, and has rekindled his relationship with his daughter, Sami, despite early conflicts over her OnlyFans career. His HIV-positive announcement in 2015 added a layer of public interest and reflection to his past, but Charlie claims he is now living a healthier, more grounded life.

While Charlie has stepped back from the Hollywood spotlight in recent years, his romantic history remains a subject of fascination, reflecting a life lived at full throttle, both on and off the screen.

Also Read: WWE Star, AJ Lee's Linkups With Popular Wrestlers, Affair With John Cena To Marriage With CM Punk

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