How Many Kids and Ex-Wives Does Charlie Sheen Have? Actor Says He's Ready for Love Again — But Not Marriage

Charlie Sheen says he is ready to fall in love again at 60 but marriage is off the table. The former Two and a Half Men star, now eight years sober, opened up as he prepares to release his memoir The Book of Sheen on 9 September 2025, alongside a two-part Netflix documentary aka Charlie Sheen debuting the following day. Marking his milestone birthday year, Sheen reflects on past marriages, fatherhood and family life while charting a new chapter.

The First Marriage: Donna Peele

Sheen's first marriage was to model Donna Peele in September 1995. The pair met during a commercial shoot earlier that year in New York. Their union was short-lived, and by 1996, the couple divorced.

The marriage produced no children and coincided with a turbulent period in Sheen's life as he faced legal troubles linked to the Heidi Fleiss trial.

Denise Richards: Marriage, Children and Divorce

Sheen met actress Denise Richards on the set of Good Advice in 2000, with their relationship developing when Richards guest-starred on Spin City in 2001. The couple married in June 2002 and went on to have two daughters, Sami, born in 2004, and Lola, born in 2005.

Richards filed for divorce in March 2005 while pregnant with their second child, citing irreconcilable differences, and the divorce was finalised in November 2006. Their split was followed by custody disputes, but in recent years the pair have displayed a more amicable co-parenting relationship.

Sheen has even appeared in support of Richards's Bravo television projects, signalling an improved dynamic between the former couple.

Brooke Mueller: Twins and Custody Battles

In 2006, Sheen began dating actress Brooke Mueller. The couple became engaged in 2007 and married in May 2008. They welcomed twin sons, Bob and Max, in March 2009. Their marriage quickly faced challenges, including Sheen's arrest on Christmas Day 2009 in Colorado on domestic violence charges.

Both Sheen and Mueller later entered rehabilitation programmes. Mueller filed for divorce in 2010, and in March 2011 police removed the twins from Sheen's home after a restraining order was issued.

Their divorce was finalised in May 2011. Custody disputes continued into the 2020s, though recent reports suggest co-parenting arrangements are more stable today.

High-School Sweetheart Paula Profit and Daughter Cassandra

Sheen's first child, Cassandra, was born in 1984 from his relationship with high-school girlfriend Paula Profit. Unlike his high-profile marriages, this relationship predated his Hollywood rise. Cassandra married Casey Huffman in 2010 and welcomed a daughter, Luna, in 2013, making Sheen a grandfather.

Other Relationships and Engagements

Beyond his marriages, Sheen's personal life included an engagement to actress Kelly Preston in 1990, which ended abruptly. He was later linked to models Bree Olson and Natalie Kenly during his 2011 'goddesses' era. In 2014, he became engaged to former adult film star Brett Rossi, also known as Scottine Ross, though the relationship ended before the year's close.

Family Life Today

Sheen is father to five children: Cassandra, Sami, Lola, Bob and Max. He is also a grandfather to Luna, now 12. His relationship with daughter Sami, now 21, has recently faced strain, though Sheen has expressed optimism about repairing their bond.

With his new memoir and Netflix documentary, Sheen is emphasising his family story alongside his Hollywood career. He has made it clear that while he is ready to embrace love again, marriage is firmly in his past, as reported by the New York Post.