1981 - 1982
Charlie Sheen was rumored to be dating American film actress Robin Wright.
Sheen and his ex girlfriend Paula Profit had a daughter together, Cassandra Jade Estevez (December 12, 1984). Cassandra was born when he was twenty, but he and Paula did not tie the knot.
1985 - 1987
Charlie Sheen dated actress Dolly Fox. Andy Warhol also mentions their affair in his diary.
Charlie Sheen dated model Valerie Barnes .
1986
Charlie Sheen dated Winona Ryder for a short time in 1986, probably after appearing in teen-oriented comedy flick Lucas together.
Charlie Sheen was rumored to be dating English socialite Tamara Beckwith.
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Charlie Sheen was rumored to be dating director Sarah Bruce.
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Charlie Sheen and porn star Teri Starr have been hooking up.
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Charlie Sheen and porn star Chloe Jones have been hooking up.
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Charlie Sheen and porn star Dominique Simone have been hooking up.
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Charlie Sheen and porn star Cathy Barry have been hooking up.
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Charlie Sheen and porn star Stacy Fuson have been hooking up.
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Charlie Sheen and the founder of the. St. Martin's Animal Foundation Sky Valencia have been hooking up.
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Charlie Sheen and porn star Charlese LaMour have been hooking up.
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Charlie Sheen and porn star Tianna Taylor have been hooking up.
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Charlie Sheen dated sex therapist Natasha Terry.
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Charlie Sheen dated Ursula Auburn.
The short-lived relationship between Charlie Sheen and Kelly Preston, which saw the pair get engaged, was marked by a bizarre incident in which Preston was accidentally shot by a loaded gun Sheen left in the pocket of his pants on a bathroom floor. Shortly after their break up in March, Preston went on to wed John Travolta.
Charlie Sheen dated Heidi Fleiss back in 1988, long before she became popular as the "Hollywood Madam".
Charlie Sheen dated American model, actress and make-up artist Cathy St. George. Cathy said of Charlie: "Let's just say he can charm the pants right off you."
1989 - 1991
Charlie Sheen dated tv personality Tracy Richman.
Charlie Sheen dated American pornographic model and actress Ginger Lynn, whom he dated on-and-off for five years. "When Charlie's sober, he's sweet, kind, loving, generous," Lynn told PEOPLE. "When he's drinking and using, he's out of control."
Charlie Sheen dated fashion model Stephanie Seymour. The two carried on a brief romantic affair in 1992 while she was still dating Guns N' Roses singer Axl Rose. The relationship played a significant role in her split from Rose and the lawsuits that followed.
Charlie Sheen met former pornographic actress Heather Hunter at a party in 1994 and briefly dated. "He was a gentleman. I think with life, people see the good side and the bad side of certain people. I never saw the (bad side) of him. I guess it was a fortunate thing."
Charlie Sheen announced his intentions to wed model Donna Peele while on the stand during Fleiss's trial in July 1995, and made good on his word on his 30th birthday, September 3. "She's an angel sent from heaven to take me through the rest of my journey," Charlie was quoted as saying.
The tumultuous affair between Charlie Sheen and Brittany Ashland ended in a June 1997 courtroom when Sheen pleaded no contest to charges of battery, with Ashland accusing her ex of throwing her onto the kitchen floor of his San Fernando Valley home and splitting her lip during a December 1996 argument.
Charlie Sheen dated pornographic actress Tabitha Stevens.
1997
Charlie Sheen dated actress Tara Phillips. Tara was in the National Enquirer with Charlie Sheen one time. She claimed she didn't like his lifestyle and had to break it off with him after a while.
1999 - 2001
Charlie Sheen dated American fashion model and actress Summer Altice. Altice said of Charlie Sheen: "I adore Charlie. Charlie and I dated three years ago right when I was leaving school. He was three weeks sober. It was more of a platonic friendship relationship. He was a very giving and caring person, and he was getting his life back together."
Charlie Sheen and Denise Richards fell in love instantly when she guest-starred on "Spin City" in 2001. They were married in 2002, where they danced to Journey's "Open Arms" then broke out into a choreographed dance routine. In 2004 they had a daughter named Sam. While 6 months pregnant with their second child, Denise revealed the two were getting a divorce. They reconciled for a while in 2005, but went through with the divorce in January 2006. Later that year Richards filed a temporary restraining order against Sheen, claiming he was doing "unstable and irrational" things around their children.
2005
Charlie Sheen dated former call girl Ashley Dupré. Ashley's former pimp revealed that she hooked up with Sheen a few years ago. Ashley Dupre was just 19 when she reportedly did the naughty with Sheen, costing him up to $20,000 a session.
Charlie Sheen and Brooke Mueller started dating in 2006 and then tied the knot in May 2008, then had twin girls in March 2009. Their affair became rocky when they got in a big fight on Christmas Day 2009, and Charlie allegedly threatened his wife with a knife. They decided to divorce in November 2010.
2010
Charlie Sheen and Colombian pornographic actress Melanie Rios have been hooking up. Melanie Rios has been telling friends she was partying alongside Kacey Jordan when 911 was called.
Charlie Sheen and porn star Capri Anderson have been hooking up.
Charlie Sheen had a fling with adult film actress Kacey Jordan. According to reports, Charlie paid her nearly $30,000 to spend two days with him.
Charlie Sheen and adult actress Bree Olson have been hooking up, with Sheen referring to Olson as one of his "goddesses," along with Natalie Kenly.
Charlie Sheen and Natalie Kenly, a model for marijuana-themed magazines, have been hooking up, with Sheen referring to Kenly as one of his "goddesses," along with Bree Olson.
What do you think of Charlie Sheen's dating history?
Photo credit: WENN
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