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  2. Jul 30, 2023 · Updated Jul 30, 2023. Link copied to clipboard. Summary. Charlie's most compatible girlfriend on Two and a Half Men was Chelsea, who challenged him and didn't tolerate his nonsense. Lisa, Charlie's old flame played by Denise Richards, was also compatible with Charlie due to her fire, kindness, and maturity.

    • Entertainment Writer
    • Missy Pyle As Miss Pasternak. Charlie Sheen's character on Two and a Half Men, Charlie Harpere, falls for Jake's teacher, Dolores Pasternak (who is played by Pyle in all appearances, bar the last one where Alicia Witt plays her.)
    • Jodi Lyn O’Keefe As Satanist Isabella. Jodi Lyn O'Keefe had the recurring role of Isabella, Charlie's girlfriend, in seasons 3, 7, and 9. Isabella is a Satanist who tries to convince Charlie to join her covenant.
    • Emmanuelle Vaugier As Charlie's Fiance. The Canadian actress plays Mia, Charlie's ex-fiancee on Two and a Half Men. The dance teacher first meets Charlie in season 3, where he pretends Jake loves dancing.
    • Ming Na Wen As Judge Linda Harris. Ming Na Wen appears in both seasons 5 and 7, playing Charlie's ex Linda Harris. Her character first meets Charlie on a double date set up by Alan, but his behavior repulses her.
  3. Two and a Half Men: Created by Lee Aronsohn, Chuck Lorre. With Jon Cryer, Angus T. Jones, Conchata Ferrell, Charlie Sheen. A hedonistic jingle writer's free-wheeling life comes to an abrupt halt when his brother and 10-year-old nephew move into his beach-front house.

    • (281K)
    • 2003-09-22
    • Comedy, Romance
    • 22
  4. Watch Two and a Half Men Streaming Now on Peacock: https://pck.tv/3wEIS6u Charlie (Charlie Sheen) has his hands full when he’s unexpectedly tasked with entertaining his...

    • 5 min
    • 403.2K
    • Peacock
  5. In the season 3 finale, Alan marries a twenty-two-year-old dumbbell named Kandi, who is one of Charlie's former girlfriends. After Charlie cancels his wedding with Mia, Alan and Kandi get married instead. However, in the season 4 premiere, four months after the marriage, Kandi throws Alan out of her condo and divorces him.

  6. When they got to Charlie's house, Charlie introduced Michelle to Berta and told Michelle about his past girlfriends and other sordid details of his life. To Charlie's surprise, Michelle still wanted to be with him.

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