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'Two and a Half Men': This Is Charlie Sheen's Dating History

CHARLIE SHEEN AND KELLY PRESTON in 1989.
May 1, 2020 - 15:35 / Anna Valenzuela Rosas

Hollywood's perpetual bad boy, Charlie Sheen has had quite a roller coaster love life. He loves to show off his gorgeous arm candy and unfortunately for him we have seen countless of them fall apart right before our eyes. This is Charlie Sheen's dating history...

Charlie Sheen's Love Life

Try to keep up. The youngest son of actor Martin Sheen, Hollywood star Charlie Sheen has had a very public life filled with erratic behavior and self-destruction. Here are some of the highlights of his dating history!

Charlie Sheen 

Paula Speert 1984-1986

While he was very young he and his high school girlfriend Paula Profit had a daughter Cassandra. Paula and Charlie only lasted 3 years but continued to raise Cassandra together. Paula has managed to stay relatively quiet in the media and live a somewhat private life.

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Charlotte Lewis 1986-1988

For a short couple years Charlie dated star of Roman Polanski's Pirates, Charlotte Lewis. The pair seemed happy together but Charlie could not hide his alcoholism long.

Charlie Sheen als "Charlie Harper"

Kelly Preston 1987-1990

Before Kelly Preston was married to Pulp Fiction's John Travolta she was shortly engaged to Charlie! The two were a powerhouse Hollywood couple who took over the world but unfortunately they also did not last. Kelly really dodged a bullet, huh?

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Speaking of bullets, there was a rumor that Charlie shot her in the arm! Both parties have spoken about the incident and explain it was an accident when the gun dropped and Kelly was merely grazed by the bullet and shrapnel. Either way, bullet(s) dodged!

CHARLIE SHEEN AND KELLY PRESTON in 1989.

Brittany Ashland 1991-1993

Charlie had begun his history of dating adult film actresses with Brittany Ashland. The two of them had a very tumultuous relationship that ended with Charlie's arrest for battery when he grabbed her by the hair and knocked her unconscious on the marble floor. Poor girl ended up needing 7 stitches!

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Ginger Lynn and Heather Hunter

After Brittany, Charlie continued dating adult film actresses, like the famous Ginger Lynn and Heather Hunter! He dates many more later. Heather famously defended Charlie during his trouble with the law when she said "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."

Donna Peele 1994-1996

Charlie married his first wife supermodel Donna Peele in 1995, but unfortunately only lasted less than a year together after it came out that Charlie had spent over 50,000 dollars on sex workers. Yikes!

Charlie Sheen and Denise Richards in 'GOOD ADVICE' 2001.

Denise Richards 2001-2006

Charlie and stone-cold fox Denise Richards met while filming together on the set of Good Advice. The Apocalypse Now actor and Super Troopers star married on June 15th, 2002. The pair ended up having two beautiful children together. 

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Again, in a similar pattern, their marriage ended intensely with Denise filing for full custody and a restraining order after Charlie made terrorizing threats.

Denise Richards and Charlie Sheen 'THE BIG BOUNCE' WORLD PREMIERE in, WESTWOOD, CALIFORNIA.

Brooke Mueller 2008-2010

Charlie and Strictly Sexual's Brooke Mueller really hit it off and married in 2008 and had twin boys together! Again, Charlie became violent and was arrested for second-degree assault, menacing, and criminal mischief. 

In this handout photo provided by the Aspen Police Department, Charlie Sheen is pictured after being arrested on December 25, 2009 in Aspen, Colorado.

Sadly, she had her boys removed from her home in 2013 during her struggle with drugs, and Denise Richards actually became their guardian until she earned custody of them again in 2014 after countless rehab stays.

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This was all only in his love life! Remember the crazy stuff he was doing in public? This was also around the time Charlie was coining the phrase "Winning" which he actually said when he was asked about him fighting for custody of his boys.

Bree Olson, Natalie Kenly, Georgia Jones, and Brett Rossi 2011-2015

This was about the time that Charlie began living and loving multiple women publicly simultaneously. He and adult film actresses Bree Olson and Natalie Kenly were in a relationship to which he referred to the two as his "goddesses". 

Charlie Sheen setzte bei der Oscar-Party von Elton John ein Statement

When he shortly thereafter announced he had been diagnosed with HIV 4 years prior, Bree took Charlie to court for not revealing to her the diagnosis. "That was when I was living with him. We were sleeping together every single night and he never said a word. Now he has to pay for what he did."

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After both left him he continued on with the Penthouse "Pet of the Month" adult film star Georgia Jones. That relationship was also short-lived as he moved on to become engaged to adult film star Brett Rossi. A month before their November 2014 wedding the pair announced they had "mutually decided" to separate. 

Charlie even shockingly said, "I've decided that my children deserve my focus more than a relationship does right now."

Julia Stambler 2017-Present

Charlie began dating the former nanny of his twin sons Julia Stambler in 2017. The two have been by each other sides since. She has openly spoken in his defense of him and her choice to date him against her friend's warnings because of his HIV diagnosis. The two have taken precautions and are continuing to go to public events and media meetings together. 

Julia Stambler and Charlie Sheen attend Project Angel Food's 23rd Annual Angel Art ART = LOVE Benefit Auction on June 23, 2018, in Los Angeles, California.