• Fri. Jun 13th, 2025

The beauties who have been with Charlie Sheen

The actor – who is causing a stir with the news of being infected with HIV – has a “romantic record” that spans Hollywood beauties, pornographic actresses and even prostitutes for “madam” Heidi Fleiss.

Kelly Preston – wife of actor John Travolta – dated Charlie Sheen for a short time in 1990. The two got engaged but then broke up.

After breaking up with the beauty Kelly Preston, Charlie entered a relationship with pornographic actress – Ginger Lynn Allen. During their 5-year relationship (from 1990 to 1995), the two broke up and got back together many times. Ginger Lynn Allen said about her lover in People magazine: “When sober, Charlie is sweet, kind and generous. When he drinks and uses drugs, he can’t control his behavior”.

Model Stephanie Seymour (who starred in the Guns N’ Roses music video “November Rain”) and Charlie Sheen began courting in 1992, when their relationships with their respective lovers were in trouble. In June 1992, Charlie Sheen confided: “We were madly in love and very happy together.”

From 1991 to 1993, Charlie Sheen was a regular customer in the prostitution ring of “madam” Heidi Fleiss. In 1993, when Heidi Fleiss was arrested, the Hollywood actor testified at the trial and admitted to spending up to $53,000 on 11 prostitutes for “madam.”

In July 1995, Charlie Sheen announced his marriage to model Donna Peele. In September of that year, the couple got married. The actor praised his wife as “an angel sent from heaven.” However, a year later, the famous playboy decided to divorce. He said of the divorce: “When you buy a bad car, it will break down.”

After separating from his first wife, Charlie Sheen started dating porn actress Brittany Ashland. Their year-long relationship ended in court in June 1997. Brittany accused Charlie of throwing her on the kitchen floor and splitting her lip during an argument. She told the judge through her lawyer: “For his own good and the good of others, he has to change his behavior.”

Charlie Sheen and actress Denise Richards married in 2002. The couple’s wedding took place in front of friends and relatives. However, when Denise Richards became pregnant with her second daughter in 2005, she suddenly filed for divorce and asked for a restraining order against her husband and her two daughters. The actress accused her husband of bringing prostitutes home to play, being addicted to online porn sites and having an unstable temperament.

Charlie Sheen’s marriage to real estate investor Brooke Mueller didn’t last long. They married in 2008 and welcomed twins a year later. However, on Christmas 2009, the “Two and a Half Men” actress was arrested for domestic violence and was later sent to rehab. Charlie Sheen and Brooke Mueller filed for divorce in November 2010, after months of separation.

Bree Olson, a former porn star, lived with Charlie Sheen in 2011. The 50-year-old actor once praised his lover as a “goddess” but quickly broke up with her.

In 2013, Charlie Sheen and adult film star Brett Rossi were spotted kissing in Cabo San Lucas, Mexico. The two got engaged in February 2014 and split later that year.

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