Top Women Charlie Sheen Has Dated

Charlie Sheen’s love life has spanned decades and included high profile romances, quick marriages, public breakups, and a few reconciliations. From early relationships before his breakout roles to the headline making chapters that followed, his dating history reflects different eras of his career and personal life. Many of these relationships involved engagements, weddings, children, or significant turning points that shaped where his story went next.

This list gathers the major women Sheen has dated or married, focusing on when they were together and what defined each relationship. You will find key timelines, family details, and pivotal events that marked beginnings and endings, along with context that explains how these connections fit into the bigger picture of his life.

Kelly Preston

Sheen and Kelly Preston were engaged around the start of the 1990s after meeting as their careers were gaining momentum. The relationship ended soon after an accidental firearm incident at his home that resulted in a minor injury to Preston. Authorities documented the episode, and the engagement was called off in the aftermath.

Following the breakup, both moved on to other relationships. Preston later married John Travolta and built a family, while Sheen continued to work steadily and entered other high profile romances that kept his personal life in the public eye.

Ginger Lynn

Adult film star Ginger Lynn dated Sheen in the late 1980s and early 1990s during a period when his star was rising in Hollywood. They were frequently linked in entertainment coverage at the time, and both acknowledged the relationship in later interviews that revisited that era.

Their on and off dynamic extended across several years, and they remained publicly cordial when discussing the past. The relationship is often cited as one of Sheen’s first widely reported romances following his early film successes.

Denise Richards

Sheen married actress Denise Richards after they met while working in the same industry and crossed paths on sets and events. They welcomed two daughters during their marriage and appeared together at public functions that highlighted their family life. Richards filed for divorce and the proceedings included custody arrangements and later modifications as their children grew.

In the years that followed, Richards and Sheen navigated co parenting while each pursued their own careers. Richards continued acting and television work and Sheen remained active on screen in projects like ‘Two and a Half Men’ and ‘Anger Management’, with both parents publicly noting efforts to keep family matters focused on their daughters.

Brooke Mueller

Real estate investor and television personality Brooke Mueller married Sheen in 2008. They welcomed twin sons the next year, and the family briefly appeared together at events that showcased their new chapter. A domestic incident in Aspen brought legal consequences for Sheen and required court monitored steps while the couple attempted reconciliation.

The marriage ultimately ended in divorce with custody and support arrangements for their twins. Both parents later worked with family courts and counselors to manage care plans as Mueller sought treatment and Sheen addressed his own health and personal challenges.

Bree Olson

Adult film performer Bree Olson dated Sheen during the highly publicized period when he referred to his household as a group of goddesses. Olson lived with him for part of 2011 and accompanied him on appearances connected with his live shows and media tour. Their relationship ended that same year as the tour wound down.

Olson later gave interviews describing day to day life in the household and the circumstances surrounding their split. She returned to her own career and public speaking while Sheen shifted his focus back to scripted television work and other projects.

Georgia Jones

Adult film actress Georgia Jones was linked to Sheen in the early 2010s. They were photographed together at events and on trips that placed them in celebrity news coverage. Reports noted their shared appearances and social media posts that hinted at a steady romance during that period.

The relationship ran its course and both moved on without a public dispute. Jones continued her modeling and media work while Sheen prepared for new television commitments and addressed personal matters that unfolded in the years that followed.

Scottine Ross

Former adult film performer Scottine Ross, also known as Brett Rossi, began dating Sheen in 2013. The couple announced an engagement on a holiday weekend the next year and discussed wedding plans that would bring together their families and friends. They called off the engagement months later and issued statements confirming the breakup.

Ross later filed a lawsuit that was resolved through a settlement after court filings and negotiations. The case coincided with Sheen’s public disclosure of his HIV status, which he discussed in interviews along with details about medical treatment and health management.

Share the relationships you think should be added to this list in the comments.