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For 12 seasons, the extremely popular show Two and a Half Men aired on CBS. People all over America and the world followed the adventures of Charlie, Alan, and Alan’s son, Jake.

Charlie, known for his slick ways and smooth talking encountered a number of women. During Charlie’s sad funeral, all 50 of his past girlfriends and hook ups showed up only to spit on his lifeless body. The character was then replaced by Walden, played by Ashton Cutcher.

While the show was mostly about the men, the women were the ones who really made the show move forward. What else would the men do other than try to get the ladies?

 

Emmanuelle Vaugier – Then

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Emmanuelle Vaugier played Mia, a dance teacher. At first, she wasn’t interested in Charlie at all. She finally fell for him and gave him one condition for dating her; he had to quit his bad habits of drinking and eating meat. Of course, he did this behind her back, which you can only imagine didn’t end well. Later on she comes back and asks Charlie for his sperm to have a baby. Rather than having a baby, he proposes to her. Just before they commit to each other, they break up because Mia wants Alan to move out of Charlie’s house.

Emmanuelle Vaugier- Now

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Emmanuelle went on to have roles in Lost Girl and Mistresses on television and in movies like Destruction Los Angeles and Washed Away.

Denise Richards – Then

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Denise Richards played Lisa. Lisa was Charlie’s girlfriend just before Alan moved into the house. They break up because Charlie can’t commit. However, late when he finds out she is engaged, he tries to win her back. It doesn’t work. Even later on she divorces her husband and gives Charlie another chance, which also doesn’t work out.

Denise Richards – Now

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Surprisingly, Denise Richards and Charlie Sheen were actually married from 2002-2006. They even have two daughters, Sam and Lola. She is still acting and as another daughter, Eloise Joni, who she adopted. She recently starred in 1st Born.

Melanie Lynskey – Then

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Melanie Lynskey played Rose, the nosy and memorable neighbor. At first, she stalked Charlie after a one-night stand. Later she became friends with the brothers. When Charlie died in Paris, it was rumored that Rose and Charlie planned to elope, but he died before they could say, “I do.”

Melanie Lynskey – Now

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Melanie still acts and has recently had roles in Sunshine, Castle Rock, and previously had a role in Sweet Home Alabama.

Jennifer Taylor – Then

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Jennifer Taylor played Chelsea, the first woman that Charlie ever said “I love you” to. She stuck around with Charlie for quite some time before she rejected his proposal and got together with Alan’s lawyer.

Jennifer Taylor – Now

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Jennifer Taylor went on to have roles in Moms ad NCIS. She is married to Paul Taylor, a songwriter. They have two children together.

Holland Taylor – Then

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Holland Taylor played Charlie and Alan’s harsh mother, Evelyn Harper. She didn’t spend much time with her boys and can be considered a gold digger.

Holland Taylor – Now

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Now in her 70’s, Holland Taylor still acts and has appeared in The Orville and Hollywood Mom. Her most recent role was in Stephen King’s Mr. Mercedes. She is currently dating Sarah Paulson.

Marin Hinkle – Then

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Marin Hinkle played Alan’s ex-wife Judith Harper. The two never had a good marriage filled with love. In fact, it was their divorce that sent Alan packing to move in with Charlie.

Marin Hinkle – Now

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Marin Hinkle has held roles in Madam Secretary, Speechless, and Homeland. She is also filming the movie, Before/During/After, set to come out soon.

Courtney Thorne-Smith – Then

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Courtney Thorne-Smith played Lyndsey. She was Alan’s on again, off again girlfriend throughout the show’s run. Fans lost count of how many times the couple broke up and got back together.

Courtney Thorne-Smith – Now

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Courtney lent her voice to Robot Chicken and guest starred on Fresh Off the Boat. She is married to Roger Fishman. They have one son together.

Allison Janney – Then

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Allison Janney played Beverly, a woman Alan met online. At first, he lied to her and said that Charlie’s house was actually his house. He later confessed when she told him of her multiple divorces. They seemed to hit it off until she abandoned Alan tied to a bed.

Allison Janney – Now

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Allison Janney has held multiple roles since her role on Two and a Half Men. She has appeared in Hairspray, The Girl on the Train, Juno, and most recently, I, Tonya. She has won an Emmy for Outstanding Supporting Actress and an Oscar.

Brooke Shields – Then

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Brooke Shields played Danielle, a woman who Charlie set up with his brother in hopes of getting him to move out of the house. However, Charlie learns that Danielle has a promiscuous past and wants her to himself leading to a fight between the brothers.

Brooke Shields – Now

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Brooke Shields is a huge name in Hollywood. Her career began way before her appearance on Two and a Half Men. Since her appearance, though, she has held roles in The Other Guys, Furry Vengeance, and Law & Order: Special Victims Unit.

Jeri Ryan – Then

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Jeri Ryan played Sherri, a woman who Charlie saw himself in. They dated for a little while until Charlie couldn’t handle how similar they were. She later dated Alan after meeting again in a doctor’s office.

Jeri Ryan – Now

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Jeri Ryan has had roles in Body of Proof, Leverage, Major Crimes, and Star Trek: Voyager. She is married to Christopher Eme, a French chef.

Kimberly Williams-Paisley – Then

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Kimberly Williams-Paisley played Gretchen. Gretchen dated Alan, who at the time was going by Jeff Strongman, his alter-ego. His excessive lying ended the relationship, obviously.

Kimberly Williams-Paisley – Now

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Kimberly went on to appear in Father of the Bride movies and According to Jim. She is married to country singer, Brad Paisley.

Judy Greer – Then

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Judy Greer played Walden’s ex-wife, Bridget. It is because of her that Walden is pushed to attempt to commit suicide in his debut episode. Eventually, Bridget wants to get back together with Walden and drives her car into his house when he rejects her.

Judy Greer – Now

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Judy Greer is one of those actresses that appears in almost everything. Since her role on Two and a Half Men, she has appeared in Archer, Entourage, Halloween, and Arrested Development.

Sophie Winkleman – Then

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Sophie Winkleman plays Walden’s girlfriend, Zoey. They date for two seasons, but the relationship ended when she rejected Walden’s proposal. Why would she say no to such a great guy? She had a side relationship.

Sophie Winkleman – Now

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Sophie Winkleman recently voiced a character on Milo Murphy’s Law and is working on filming Trust. She is also married to some royalty. Her husband, Lord Frederick Windsor is the son of the cousin of Queen Elizabeth II.

Ming-Na Wen – Then

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Ming-Na Wen played Linda, one of Charlie’s girlfriends. At first, she didn’t like Charlie. Some time later, when Charlie is brought to court for a DUI, Linda is the judge for his case. Finally, Charlie convinces her to go out with him and they date for a little while until Charlie embarrasses her at an awards ceremony.

Ming-Na Wen – Now

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Ming-Na Wen is best known for her voice acting as Mulan in Disney’s animated movie, Mulan before her time on Two and a Half Men. She has appeared in ER, Eureka, and Agents of S.H.I.E.L.D.

Heather Locklear – Then

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Heather Locklear played Alan’s divorce attorney, Laura. She is fierce inside and outside of the courtroom. When Charlie decides he wants to hook up with her, she makes him promise to always be on call for her. When Charlie finds himself in a relationship, she is not happy and starts sabotaging Alan’s divorce.

Heather Locklear – Now

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Heather Locklear has appeared in titles such as Melrose Place, Franklin & Bash, LAX, Scary Movie 5, and Too Close to Home.

Gail O’Grady – Then

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Gail O’Grady played Mandi. Mandi is the mother of Alan’s wife, Kandi. She comes to the house looking for her daughter when she meets Charlie and they hit it off. Charlie, of course, didn’t know that she was Kandi’s mother.

Gail O’Grady – Now

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Gail has recently appeared in Lycan and Revenge since her role in Two and a Half Men. Throughout her life, she has been married a total of 6 times. She was divorced most recently in 2008.

Paula Marshall – Then

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Paula Marshall played Paula, a woman who had had a sex change operation. When she met Alan in a club, the two hit it off and he didn’t mind this fact. However, they decided to be in an open relationship. When Alan starts dating Paula’s ex-wife, Rachel, Paula gets jealous, kisses Rachel, and they get back together.

Paula Marshall – Now

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Paula Marshall has appeared in Murder in the First, Gortimer Gibbon’s Life on Normal Street, and We Love You, Sally Carmichael.

Missi Pyle – Then

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Missi Pyle played Jake’s teacher, Miss Pasternak. She dated Charlie for a while and boosted Jake’s grade during the relationship. However, once Charlie found out she had a mental illness, he dumped her. Later, she loses her teaching license and works as a an exotic dancer, then moves in with Charlie to tutor Jake.

Missi Pyle – Now

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Since Two and a Half Men, Missi has had roles in Inside Amy Schumer, The Soul Man, Sing It!, Gone Girl, The Artist, and Jumanji: Welcome to the Jungle.

Kimberly Quinn – Then

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Kimberly Quinn played Donna, Alan’s brief girlfriend. She met Alan on the same blind date that Charlie met Linda, the judge. However, Alan wanted to end the relationship, but didn’t know how. So, he went to Charlie for advice.

Kimberly Quinn – Now

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Kimberly Quinn as appeared in Gypsy and Twisted since her role on Two and a Half Men.

Tammy Lauren – Then

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Tammy Lauren plays Shannon, the ex-fiancé of the man who Judith, Alan’s ex-wife, is marrying. Alan and Tammy hook up at the wedding and concoct a plan to make their ex’s jealous.

Tammy Lauren – Now

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Tammy Lauren has had roles in Criminal Minds and The Young and the Restless since appearing on the show. However, she halted her acting career in 2014.

Justine Eyre – Then

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When Charlie reveals that he stole Alan’s girlfriend, Charity, in high school, Alan sets out to hook up with Charlie’s girlfriend, Gabrielle, played by Justine Eyre. Unfortunately, this didn’t work out for Alan.

Justine Eyre – Now

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Justine has guest starred on shows such as CSI: Miami, The Secret Life of the American Teenager, and voiced characters in Uncharted 4: A Thief’s End.

Maggie Lawson – Then

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Maggie Lawson plays social worker, Ms. McMartin. When Walden decides he wants to adopt a child, he decides that it would be an easier process if he were in a gay relationship. This results in convincing Alan to pretend to be gay with him. However, when he sees that his social worker is beautiful, he tries to date her. This obviously doesn’t work out and the little boy is taken away from him. Alan fixes the situation by hooking up with her and she lets the two men keep the child.

Maggie Lawson – Now

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Maggie Lawson went on to appear in Angel from Hell, Psych, and The Great Indoors.

Krista Allen – Then

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Krista Allen played Olivia, a former girlfriend of Charlie. Needless to say, the relationship didn’t end well. In fact, when the two see each other again, she throws a drink in Charlie’s face.

Krista Allen – Now

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Before appearing on Two and a Half Men, she starred in Days of Our Lives and The Final Destination. She can be seen in the upcoming Eleven Eleven and Best Moms.

Teri Hatcher – Then

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Teri Hatcher played Alan’s ex-wife’s sister. At the wedding, Liz and Charlie hooked up, but she never remembers meeting him. During the show, it’s revealed that Alan asked Liz out before her sister, Judith. The sisters tried to get back at each other by hooking up with the opposite brother, but they couldn’t go through with it.

Teri Hatcher – Now

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Teri Hatcher is best known for her role in Desperate Housewives. She also appeared in The Odd Couple and Supergirl.

Kristin Dattilo – Then

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Kristin Dattilo played Cindy, a woman who never falls for Charlie’s charm throughout the show. Jake develops a crush on her and starts drawing her in art class. She even becomes BFFs with Judith, which led Alan to think they were lovers.

Kristin Dattilo – Now

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Kristin Dattilo has appeared in Dexter, Grounded for Life, The Chris Isaak Show, and How to Get Rid of a Body (And Still Be Friends).

Liz Vassey – Then

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Liz Vassey played two women on the show, Kate and Michelle. Kate, a single mom, dated Charlie for a brief moment. She then came on the show again as Michelle, Charlie’s dermatologist. They also dated for a little while.

Liz Vassey – Now

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Liz Vassey is best known for her role in CSI: Crime Scene Investigation and also appeared in Nikki & Nora: The N&N Files and Riley Para.

Paget Brewster – Then

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Paget Brewster played childhood friend of Charlie and Alan, Jamie. In high school, she had been overweight and nicknamed “Eckleberry Hound.” When they meet as adults, she is in shape and drop dead gorgeous. Of course, the brothers want to get with her instantly.

Paget Brewster – Now

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Paget Brewster is best known for her role as Emily Prentiss in Criminal Minds. She has been on the show since 2006.

Rachel Cannon – Then

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Rachel Cannon played Chloe, one of Charlie’s girlfriends. Charlie wants to break up with Chloe. When Chloe falls for the handyman (Enrique Iglesias) when he comes to fix something in the house, Charlie gets jealous and wants her back.

Rachel Cannon – Now

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Rachel Cannon has had roles in Mad Men, Ghost Whisperer, Underemployed, The Big Bang Theory, and Fresh Off the Boat.

Sara Rue – Then

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Sara Rue played Naomi, Bertha the housekeeper’s daughter. When she first appears on the show she is pregnant. She falls of Alan and kisses him for the first time just before going into labor. They date secretly, but the relationship doesn’t go anywhere.

Sara Rue – Now

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Sara Rue has appeared in Rules of Engagement, Mom and Bones, Impastor, Popular, and A Series of Unfortunate Events. She can be seen in films such as Pearl Harbor and The Ring.

Stephanie Jacobsen – Then

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Stephany Jacobsen played Penelope, a bikini babe hanging around Charlie’s house. She meets Walden, who has just bought the house and learns about Charlie’s death. For a moment she is stunned, until she sees how handsome Walden is.

Stephaney Jacobsen – Now

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Stephany Jacobsen is best known for her role as Charlotte Adams in Home and Away. She also appeared in Star-Crossed, Revenge, and Occupation.

Jaime Pressly – Then

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Jaime Pressly plays Tammy, a 36-year-old single mother who owns a tattoo parlor. She starts dating Jake in the show’s 10th season. The relationship didn’t last long since Jake hooked up with Tammy’s daughter.

Jaime Pressly – Now

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Jaime Pressly has appeared in I Love You, Man, Not Another Teen Movie, and Mom since her role on the Two and a Half Men.

Miley Cyrus – Then

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Miley Cyrus played Missi. Missi meets Jake when he is home one weekend from the Army. They hook up and she reveals that she has a boyfriend. That doesn’t stop Jake from dropping out of the Army and confessing his love for her. She then convinces him to go back to the Army.

Miley Cyrus – Now

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Miley Cyrus is best known for her role as Hannah Montana. She doesn’t act so much anymore, but focuses on her music. Her most recent album is titled Malibu.

Megan Fox – Then

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Megan Fox played Prudence. Prudence is Bertha’s teenage granddaughter. All three men develop a crush on her when she comes to the house with her grandmother. You can only imagine how that turned out.

Megan Fox – Now

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Megan Fox has starred in Transformers, Hope & Faith, and New Girl since her role on the show.

Conchata Ferrell – Then

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Conchata Ferrell played everyone’s favorite female character on the show, Bertha. Bertha was Charlie’s housekeeper. She was feisty and full of jokes about the brothers.

Conchata Ferrell – Now

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Since the show ended, Conchata has appeared in Krampus and The Ranch. She is married to Arnie Anderson.

Kelly Stables – Then

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Kelly Stables played Melissa. Melissa was Alan’s secretary and also dated Charlie for a short while. After that relationship ended, she grew attracted to Alan. They eventually move in together in the show’s 8th season, but Alan ends the relationship over text.

Kelly Stables – Now

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Since the show, Kelly can be seen in Horrible Bosses 2 and Exes. You can also hear her voice Will Vandom in W.I.T.C.H.

Jenny McCarthy – Then

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Jenny McCarthy played Courtney, the daughter of the man the boys’ mother was engaged to. They both found their soon-to-be stepsister extremely attractive and wanted to date her. They soon realize that Courtney and her “father” are con artists.

Jenny McCarthy – Now

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Before guest starring on the show, Jenny McCarthy was a Playboy model. She is married to Donnie Wahlberg.

April Bowlby – Then

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April Bowlby played Kandi, a girl in her early twenties who hooks up with both brothers and Judith’s divorce attorney. She married Allen in Vegas and divorces Alan when she gets an acting role on a detective show.

April Bowlby – Now

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April Bowlby went on to star in Drop Dead Diva and appear in Mom and The Big Bang Theory. She is currently dating Josh Groban.

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