Celebrity Exes
Charlie Sheen’s Dating History: His Girlfriends, Ex-Wives & More
Since the 1980s, Charlie Sheen‘s life has been in the spotlight, but it hasn’t always been for the best reasons. Now nearly eight years sober, Sheen is ready to tell his story in a memoir, The Book of Sheen, and a Netflix documentary, aka Charlie Sheen.
In addition to his own personal struggles, Sheen has also made headlines for his relationships over the years. After three marriages and five engagements, he’s been through it in the love department.
Amid his sobriety journey, Sheen said he’s also been celibate, and told People his love life is currently “uneventful.” While he’s single right now, though, he admitted to being “open” to falling in love again. “If somebody walked through the door and it was the right time and you can’t deny it … absolutely. Probably not marriage, though,” he shared.
Scroll down for a refresher on all of Sheen’s past public romances with Denise Richards and more.
aka Charlie Sheen, Wednesday, September 10, Netflix
Kelly Preston
Sheen started dating Kelly Preston in 1989, and they were even engaged. However, the relationship ended in early 1990 after she was accidentally hit with shrapnel from a loaded gun that he’d left on the bathroom floor.
Prior to his relationship with Preston, Sheen dated his high school girlfriend, Paula, with whom he shares his eldest daughter, Cassandra (born in 1984).
Stephanie Seymour
In 1992, Sheen allegedly dated supermodel Stephanie Seymour and claimed they were “madly in love,” despite her being in a relationship with Axl Rose at the time.
Ginger Lynn Allen
During the first half of the 1990s, Sheen was in an on-and-off relationship with adult film star Ginger Lynn Allen. He also dated adult film star Heather Hunter during this time.
Donna Peele
Sheen got married for the first time to Donna Peele in September 1995. However, it was short-lived, as they divorced the following year.
Amid his marriage to Peele, it was confirmed that Sheen had been one of the clients of Heidi Fleiss, who operated an escort agency. During her 1995 trial for tax evasion, he took the stand and said he spent more than $50,000 on 11 of her prostitutes.
Sheen was also briefly in a relationship with Brittany Ashland in 1996. The following year, she filed a lawsuit against him, and he was charged with misdemeanor battery with serious injury.
In June 1997, Sheen pleaded no contest to the charges and was given a one-year suspended prison sentence and two years’ probation.
Denise Richards
Sheen met Richards in 2000, but they didn’t start dating until the following year when she made an appearance on his show Spin City.
The two tied the knot in 2002 and welcomed daughters Sami and Lola together.
Richards filed for divorce from Sheen in 2005 while she was pregnant with Lola. Although they attempted to reconcile, they continued with the divorce in 2006 and were eventually involved in a messy custody battle.
Sheen and Richards have had many ups and downs over the years, including when she sued him in 2016 with claims that he didn’t provide financial support he promised for their daughters. However, today they are on amicable terms, and she was even at the premiere for his Netflix doc.
Brooke Mueller
Sheen started dating Brooke Mueller shortly following his divorce from Richards. They tied the knot in 2008, and their twin sons, Bob and Max, were born the following March.
That December, Sheen was arrested for domestic violence after Mueller accused him of holding a knife to her throat. However, he insisted that she was the aggressor, and a temporary protection order was put in place. They both checked into rehab, and Sheen eventually pled guilty to a lesser sentence, which allowed him to serve time in rehab, rather than jail.
Both Sheen and Mueller filed for divorce in November 2010, although they’d separated nearly a year earlier. They dealt with custody issues following the split, with Richards even stepping in to care for the twins in 2013 amid Sheen and Mueller’s respective troubles.
Like Sheen, Mueller is now sober (although she relapsed in 2023 after six years of sobriety).
“We share custody, we coparent without attorneys, which is great,” Mueller told People. “And I’m very grateful for that. The fact he gives me yet another chance shows his deep true heart underneath.”
Bree Olson
In 2011, Sheen had live-in women whom he called “goddesses,” including adult film star Bree Olson and graphic designer Natalie Kenly.
Olson ended her relationship with Sheen that April, and Kenly followed suit in June.
Brett Rossi
Sheen started dating another adult film star, Brett Rossi, whose real name is Scottine, in 2013. They got engaged in February 2014 but called off their planned wedding eight months later.
In 2015, Sheen went public with his HIV diagnosis, prompting Rossi to sue him for assault and battery, emotional distress, false imprisonment, and negligence, according to People. She accused Sheen of becoming “violent and abusive and uncontrollable” at times during their relationship.
Rossi also claimed that Sheen never disclosed his HIV diagnosis to her and said he forced her to have an abortion in 2014. The case was referred to arbitration and settled out of court.
