Two And A Half Men: Charlie's Girlfriends, Ranked In Order

Name: Two And A Half Men: Charlie's Girlfriends, Ranked In Order
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The Women Of ‘Two And A Half Men’ And Where They Are Now - Brake For It
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The Women Of ‘Two And A Half Men’ And Where They Are Now
Burtland Dixon | Trending | 27 Apr 2026
The television sitcom Two and a Half Men premiered in 2003, starring Charlie Sheen as Charlie Harper, Jon Cryer as Alan Harper, and Angus T. Jones as Jake Harper. The series followed the two and a half men as Sheen's character lives a hedonistic life. That lifestyle led to many dates with beautiful women as the series progressed.
Take a look at all of the women Charlie Harper dated and what the actresses are up to now.
Miley Cyrus - "Missi"
The WB Television/ MovieStillsDB/Dia Dipasupil/WireImage
Outside of Alan's and Charlie's plethora of flings and girlfriends, what fans really liked to see was any of Jake's love interests. After all, the kid has been on the show since he was, well, a kid and it's always interesting to see how they grow up. One of his first girlfriends was Missi, though we don't meet this character until season ten.
Missi first appears in the episode "You Do Know What The Lollipop Is For," when Jake comes home from the Army. After Jake goes AWOL, Missi feels uncomfortable about his feelings for her and she convinces him to return to the Army.
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Kelly Stables - "Melissa"
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The WB Television/MovieStillsDB/Tibrina Hobson /Getty Images
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A woman who had a recurring role on the show was Melissa, played by Kelly Stables. She was Alan Harper's receptionist, who Charlie tried to get to fall for him. Eventually, she started a relationship with Alan. The relationship ends with Alan breaking up with her over a text.
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Stables was also a recurring character on the TV show Superstore . She's landed plenty of roles throughout her acting career as well. Stables has a husband, Kurt Patino and two children.
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Jeri Ryan - "Sherri"
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Sherri was a type of girl Charlie had never encountered before. She was very skilled at the art of playing hard to get and would constantly lead Charlie to have relations with her. He thought he was the one getting used so he plotted revenge and that's what led to their downfall.
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Jeri Ryan might be best known for her role on Star Trek: Voyager which helped her earn four Saturn Awards. Her latest work is a project called The Relic .
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Brooke Shields - "Danielle Stewart"
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Brooke Shields played a girl with a partying past, but that didn't stop Charlie from setting her up with Alan. Alan tells Danielle Stewart that he's going to change for her, something no other guy has told her. After Danielle tells Charlie, "I've slept with a lot of guys and even a few women and even with couples," he all of a sudden wants her and fights Alan, causing her to leave.
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Clearly, Shields was already a prominent actress before she appeared on this show. She grabbed her first lead role at the age of 12. You might have caught her on Law & Order: Special Victims Unit .
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Jenny McCarthy - "Courtney Leopold"
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The WB Television/ MovieStillsDB/Taylor Hill/FilmMagic
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"Courtney Leopold" first appears in season five as the daughter of one of Evelyn's suitors, Teddy. Eventually it's found out that Courtney was a former Con-Artist, who also goes by the name of Sylvia Fishman. Sylvia returns in season eight and again in season nine, always up to her scheming ways.
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She was played by none other than Jenny McCarthy who is recently a judge on The Masked Singer . She also had a recurring role on Return of the Mac and on The Real Housewives of Beverly Hills .
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Heather Locklear - "Laura"
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While Alan was going through a rough patch trying to get his divorce settled, something happened. In true Charlie fashion, he messed things up by sleeping with Alan's attorney, Laura. After Charlie broke his promise being available to her whenever she wanted, she sabotaged Alan's divorce proceedings.
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Even before appearing on the show, Heather Locklear was a well-established name. She's fought through a publicized divorce and a few health issues.
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Denise Richards - "Lisa"
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Lisa appears in season one as one of Charlie's exes who he desperately tries to win back. Charlie lies to her by saying he has turned into a family man but it actually turns out that he has commitment issues. Lisa was played by Denise Richards, who was Charlie Sheen's wife in real life at the time.
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Shortly after her stint on Two and a Half Men , Richards filed for divorce. She and Sheen share two daughters together. She went on to appear on The Real Housewives of Beverly Hills and The Bold and the Beautiful .
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Jennifer Taylor - "Chelsea"
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At the beginning of Charlie's relationship with Jennifer Taylor's character Chelsea, he strictly saw her as a one-night stand. Over time, that changed as Charlie began to grow feelings for her. As a result, Chelsea had the pleasure of becoming the first woman Charlie ever professed his love to. She ends up leaving him for Alan's lawyer.
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Taylor is now married to Paul Taylor. One of her most recent TV appearances comes from the hit series Shameless .
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Allison Janney - "Beverly"
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Alan met Allison Janney's character Beverly via a dating site. He really wanted to impress her so he told Beverly that the beach house was all his. Upon feeling bad about her recent divorce issues, he comes clean and reveals that the house is Charlie's.
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How could you not recognize Allison Janney? She's been in hit movies like Hairspray and Juno . The work she's done in acting has earned her seven Primetime Emmy Awards, a Golden Globe, and Academy Award, and much more!
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Teri Hatcher - "Liz"
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Liz appears in season one of Two and a Half Men as Judith's "sleaze-ball" sister. At Alan and Judith's wedding, Liz and Charlie did the deed in the coat closet, which afterward leaves Charlie befuddled when she doesn't recall the encounter. Liz was played by Teri Hatcher.
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Hatcher is best remembered for her role as Lois Lane on Lois & Clark: The New Adventures of Superman and as Susan Mayer on Desperate Housewives . The Golden Globe-winning actress has recently appeared on Supergirl , QI , and All Round to Mrs. Brown's .
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Courtney Thorne-Smith - "Lyndsey McElroy"
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Courtney Thorne-Smith played a slightly masculine character by the name of Lyndsey McElroy. She enjoyed drinking beer and was Alan's on-and-off romantic partner. She had a serious drinking problem as well. She was very caring, but also a super flirt.
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Smith played this role for five years and once it ended, she took a break from the Hollywood lifestyle. She did do a voice a character on the adult cartoon show Robot Chicken before appearing on Fresh Off The Boat .
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Judy Greer - "Bridget Schmidt"
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As Ashton Kutcher's character gets into the swing of things, the audience soon finds out about his past aka his divorce with Bridget Schmidt. He loved her so much that he was willing to take his life for her. After she discovers that he's dating someone else, she tries to get him back but it was too late.
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Judy Greer is a we…

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