Charlie Sheen's Marriage and Relationship History

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Back in 1986, Sheen shared a short-lived relationship with Winona Ryder, an American actress. The duo met while auditioning for a film that they later starred in. Despite the enticing chemistry, their relationship didn't last longer than a few months. Rumors persist that their breakup was mutual, as both decided to concentrate on their burgeoning careers.

Charlie Sheen had a brief, yet significant relationship with esteemed actress Robin Wright. They dated in 1981 after meeting at a celebrity party. Despite the strong initial attraction, they decided to part ways after a year of dating due to personal differences. The reasons for their breakup remained personal and was not aired in public.