Inside Charlie Sheen's Personal Life: His Wives and Kids

Tue Jun 27 2023
By   tashi

Charlie Sheen has been married three times: Inside the actor's troubled personal life!  

Known for his roles in Wall Street, Spin City, Two and a Half Men, Anger Management, and more, Charlie Sheen boasts quite a stellar career. Previously ranked one of the highest-paid actors on television, Sheen has been an active member of the industry since the 1980s.  

Born on September 3, 1965, in New York City, to actor Martin Sheen, and artist Janet Templeton, Charlie has two older brothers, and one younger sister, all in the acting business. Despite achieving a formidable name in the industry, Sheen has garnered a stigmatized reputation. Throughout his life in the spotlight, Sheen has been a part of many scandals. 

Inside Charlie Sheen's Dating History!   

A Lover but not a very good one. Sheen's disgraceful moments or stints over the years also include the actor's relationships with a slew of women. Among the legion of women that he dated, three of them ended up being his wife, and later ex-wife. The Two and a Half Men actor's dating career goes back to his high school days.   

Charlie Sheen is best known for his roles in Spin City and Two and Half Men.
Sheen has been married three times. Photo Source: Instagram

Sheen shares his oldest daughter with his high school sweetheart, Paula Profit. Charlie's first public relationship, after his gradual rise to fame, was with actress Kelly Preston. The pair were engaged at one point but a gruesome event changed the course of their relationship.  

Kelly, who died of cancer in 2020, allegedly broke off her engagement with Sheen after he shot her in the arm. The Spin City actor would go on to get casually involved with several pornstars after his failed engagement, including with Ginger Lynn, and Heather Hunter.    

Charlie sheen has been married three times.
Sheen was accused of shooting his ex-fiance, Kelly Preston, in the arm. Photo Source: Instagram

Sheen married his first wife, Donna Peele, an upcoming model back then, in September 1995, after just six weeks of knowing her. It was no surprise when the duo's whirlwind romance and marriage ended with the actor filing for divorce in November 1996.  

Sheen was taken into custody the same year in an alleged assault of a former girlfriend, Brittany Ashland. Know that the actor's relationship scandals were recurring headlines alongside his on-and-off rehab stint. Sheen's most notable and notorious relationship was with actress Denise Richards.  

Charlie and Richards met on the sets of Good Advice in 2000 and started dating shortly after. The couple walked down the aisle in June 2002 and welcomed two daughters before calling it quits in 2005. But the pair's split was a far cry from amicable.   

Charlie Sheen reportedly shot an ex-fiance.
Sheen and Denise Richards were married from 2002 to 2005. Photo Source: Instagram

The estranged pair has had some nasty public spats over the years. Richards once even sued the actor for $1.2 million for not providing child support. The duo continues to rake in negative publicity amid their daughter, Sami's OnlyFans endorsement and tarnishing comments about her family. 

The Two and a Half Men actor married his third wife, actress Brooke Mueller in May 2008, and welcomed twin sons, with her. And like most of his previous relationships, this one, too, was a short, and disgraceful trip. A year after their nuptial, Sheen was arrested on suspicion of domestic abuse. The pair's marriage ended with Mueller obtaining a restraining order against the actor.   

Who is Charlie Sheen Dating?  

Sheen's bitter experience in love continued after his divorce from Mueller. In an infamous turn of events, the Spin City actor even had a polyamorous relationship with pornstar Bree Olsen, and designer Natalie Kenly, in 2011. Sheen was even engaged to adult movie star, Brett Rossi, in 2014.   

Charlie Sheen is battling HIV.
Sheen was last reported to be dating model Julia Stambler. Photo Source: Instagram

The Two and a Half Men actor is believed to be in a long-term relationship with a young model named Julia Stambler, with whom he was first linked in 2017. The television actor has, however, more serious things to be worried about than his love life. Charlie revealed his HIV-positive diagnosis in 2015.  

The disclosure prompted many women to accuse the actor of putting them at risk, including Sheen's ex-fiance, Rossi, who sued him following the revelation. But Charlie's latest flame, Stambler, is allegedly not scared of his disease.    

Sheen revealed his HIV-positive diagnosis in 2015! 

Although we haven't heard of the pair in a long time, a source previously reported that Sheen and his girlfriend are taking every measure to keep it safe. The actor recently gave fans an insight into his battle with the disease. "I'm so grateful for what was available when it happened and even more grateful for what's available right now," the actor explained.  

Who are Charlie Sheen's Five Kids?  

Sheen delved into fatherhood pretty early on. Considering that he had his first child at the age of 19, Sheen's parenting experience is as old as his career. The Two and a Half Men actor, across his controversies, and scandals, may not come off as the best father though.   

Charlie Sheen is a father to five.
Sheen has five kids across three relationships. Photo Source: Instagram

Sheen's oldest child, Cassandra Estevez, was born to him and his high school sweetheart, Paula when he was 19. Cassandra made Sheen a first-time grandpa when she and her hubby welcomed a baby, in 2013. "It's impossibly a most wondrous day," the actor said upon becoming a grandpa.  

Charlie shares his next two kids, Sami, and Lola, with Richards. The duo's daughter, Sami, has been the catalyst of many family dramas since joining the adult subscription platform, OnlyFans, in 2022. Sheen initially reproached Sami's decision before getting on board with Richards to show his lukewarm approval.  

Lola Sheen, 18, on the other hand, is the complete opposite of her OnlyFans model sister. Despite her parents' ruckus-filled period in the past and her sister's ongoing drama in recent times, Lola has successfully remained out of the spotlight. The teenager is reportedly living with her mother after moving out of her dad's house earlier this year.  

Charlie's two youngest kids, Bob, and Max, were born to him and his third ex-wife, Brooke. The Spin City actor had a lengthy custody battle with Brooke over his twin kids. The duo later settled the case in private and confident. The actor was recently spotted enjoying a sunny day with his twins, who many alleged were spitting image of the actor. 

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