What Are The Women of Two And A Half Men Up To Now?


Although the show was called Two and a Half Men, plenty of women graced the screens. Throughout the twelve seasons of the show, we saw many notable faces, but who were the ones that fell for the guys’ tricks?

Marin Hinkle as Judith Harper-Melnick | Then

Marin was a regular feature as the demanding ex-wife of Alan. The exes shared a bizarre relationship as they tried to co-parent their son Jake, and were often butting heads about paying child support and alimony. Alan would often call out Judith for spending that money on cosmetic surgery and luxury goods, rather than on their son. Things got more complicated when Judith found love with Jake’s doctor, but their marriage ended in divorce when she discovered that he was having an affair.

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Marin Hinkle as Judith Harper-Melnick | Then

Marin Hinkle as Judith Harper-Melnick | Now

When Two and a Half Men came to a end, Hinkle managed to move on to other successful projects in acting, and took up a part in the CBS series Madam Secretary. Moreover, her other roles have been in Speechless, and as Christine Lonas in a more serious role on Homeland. Hinkle also starred in a number of movies and recently wrapped filming on Before/During/After. Despite acting as the crazy ex-wife, Marin has had a long and happy marriage to Randall Sommer.

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Marin Hinkle as Judith Harper-Melnick | Now

Emmanuelle Vaugier as Mia | Then

When Charlie set his eyes on a lady, nothing would stop him until he conquered his mission and that is exactly what happened when he met dance teacher, Mia. Charlie forced Jake to dance so that he could get closer to the brunette, and agreed to abide by her conditions of giving up meat, smoking, and drinking so that she would go on a date with him. Charlie agreed, but continued to do it all behind her back, resulting in Mia leaving him.

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Emmanuelle Vaugier as Mia | Then

Emmanuelle Vaugier as Mia | Now

When Vaugier’s stint on Two and a Half Men was finished, her career was on the up and she took on roles on TV shows including Lost Girl, One Tree Hill, Rogue, and Mistresses. Her prominence landed her a spot on Maxim’s “Hot 100 list.” In addition, Emmanuelle ventured into movies and appeared in films including Destruction Los Angeles and Washed Away. Nowadays, the 41-year-old actress is working on a thriller titled Masks Don’t Lie, set in Venice, Italy.

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Emmanuelle Vaugier as Mia | Now

Holland Taylor as Evelyn Harper | Then

One woman that was a constant feature in both Charlie and Alan’s life was their mother, played by Holland Taylor. Their relationship was complicated and Evelyn was only women on the show who could tell her sons exactly what she thought without them leaving her. Despite having a reputation for being a gold-digger and dating older men, purely to steal their assets, she was a big hit with audiences. It was safe to say that Charlie and Alan avoided her at all cost.

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Holland Taylor as Evelyn Harper | Then

Holland Taylor as Evelyn Harper | Now

Holland Taylor is an extremely recognizable face in Hollywood and has been a prominent actress since the 80s. For her role on Two and a Half Men she has been nominated four times since 2003, for Best Supporting Actress for her role on the TV series Two and a Half Men. In addition, Taylor famously starred in the 2001 comedy Legally Blonde, alongside Reese Witherspoon. Today, Taylor is taking on the part of Ida Silver in the show Mr. Mercedes.

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Holland Taylor as Evelyn Harper | Now

Melanie Lynskey as Rose | Then

No one could forget Rose, who fell madly in love with Charlie after they spent the night together, and she couldn’t let him go. Rose developed an obsession with Charlie and wouldn’t take no for an answer, going so far to stalk him at his house. However, things turned around from Rose and Charlie agreed to marry her and the two ran off to Paris together. Unfortunately, it was all too good to be true and Charlie died before they tied the knot.

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Melanie Lynskey as Rose | Then

Melanie Lynskey as Rose | Now

Lynskey’s early films included Sweet Home AlabamaHeavenly Creatures, and Coyote Ugly. However, it wasn’t until later in her career that Rose was cast in leading roles and she ended up starring in films including Hello I Must Be Going, followed by Happy ChristmasThe Intervention, and I Don’t Feel at Home in This World Anymore. Melanie was previously married to fellow actor Jimmi Simpson from 2007 until 2014, and is now engaged to Jason Ritter.

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Melanie Lynskey as Rose | Now

Jennifer Taylor as Chelsea Melini | Then

Chelsea Melini was one of the most prominent women on the show, particularly due to the fact that she was the first woman Charlie confessed his love for. Despite Charlie putting his heart on the line for the first time, Chelsea grew tired of the playboy and ended up leaving him for Alan’s lawyer.

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Jennifer Taylor as Chelsea Melini | Then

Jennifer Taylor as Chelsea Melini | Now

When Jennifer was first written into Two and a Half Men, she wasn’t intended to have stolen the heart of the main character on the show, but her appearances became frequent once she did. After her departure from the show, Taylor continued to act, taking on guest roles on series including Shameless, NCIS and Mom. In her personal life, Taylor found love with songwriter Paul Taylor and the couple have two children together.

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Jennifer Taylor as Chelsea Melini | Now

Allison Janney as Beverly | Then

After Alan met Beverly on a dating website, he decided to lie and claim that the house belonged to him in an attempt to impress her. Alan didn’t come clean until Beverly opened up about her failed marriages, leading Alan to feel guilty about lying to her. When he finally admitted the truth, Beverly didn’t seem to care and they continued with their relationship. However, things finally ended when Charlie walked in on Alan being tied up by Beverly.

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Allison Janney as Beverly | Then

Allison Janney as Beverly | Now

Janney was a well known actress in Hollywood long before appearing as Alan’s love interest on Two and a Half Men. She also appeared in The West Wing, between the years of 1999-2006, before making the transition to feature films. She has starred in award-winning films including Juno, Hairspray, and The Girl on the Train. Nowadays, the actress plays Anna Faris’ mother on CBS sitcom, Mom, of which she won an Emmy award for.

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Allison Janney as Beverly | Now

Jeri Ryan as Sherri | Then

When Sherri came along, it was thought that Charlie had met his match. She was not someone that would fall for his tricks that seemed to work on every other woman Charlie had been with. At first, Sherri’s attitude of playing hard to get way very attractive, but Charlie grew tired of her being one step ahead of him. Eventually, the two called it quits, but not before she tried her luck with Alan, which didn’t work either.

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Jeri Ryan as Sherri | Then

Jeri Ryan as Sherri | Now

Jeri Ryan is best known for her role as the Borg Seven of Nine on Star Trek: Voyager. In addition to the sci-fi shows, she had appeared on Major Crimes, Body of Proof, Helix, and Law & Order: Special Victims Unit. Ryan was previously married to Republican political candidate Jack Ryan but the two divorced due to their conflicting schedules. Nowadays, she is happily married to her French chef husband, Christophe Eme, and the couple have two children together.

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Jeri Ryan as Sherri | Now

Kimberly Williams-Paisley as Gretchen Martin | Then

Alan begins dating Larry’s sister Gretchen Martin, but once again, he couldn’t tell the truth about his life. He told her that Jake’s apartment was actually his and that he does not live with Charlie. The lies began racking up and it became to much for Alan to keep up with. When Gretchen found out about the fallacies, she dumped Alan and explained that she was married to a compulsive liar and didn’t want to go through it again.

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Kimberly Williams-Paisley as Gretchen Martin | Then

Kimberly Williams-Paisley as Gretchen Martin | Now

Kimberly had been acting from a young age and one of her most notable roles was opposite Steve Martin in the famous romantic comedy Father of the Bride. In addition, the actress appeared on According to Jim for an impressive eight years. Recently, it was revealed that Kimberly filmed a holiday movie titled The Christmas Train as well as another movie titled Darrow and Darrow. Kimberly has been married to country singer Brad Paisley since 2003.

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Kimberly Williams-Paisley as Gretchen Martin | Now

Ming-Na Wen as Linda Harris | Then

Linda was introduced to Charlie after Alan planned a double date for them. Immediately, Charlie was very attracted to Linda but she could see right through his personality and turned his advances down, time and time again. However, things changed when Charlie was charged with a DUI and Linda was the judge that he went up against. Following this incident, she decided to give him another chance, but it didn’t go on for too long.

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Ming-Na Wen as Linda Harris | Then

Ming-Na Wen as Linda Harris | Now

Interestingly, Ming-Na Wen was not new to Hollywood, but she wasn’t used to being in front of a camera too much. This is due to the fact that she voiced the Disney character, Mulan, in both of the movies. She also voiced a character in  Sofia the First, and is due to reprise her role as Mulan in Ralph Breaks the Internet: Wreck-It Ralph 2. In front of the camera, she has starred in shows including Eureka and SGU Stargate Universe.

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Ming-Na Wen as Linda Harris | Now

Gail O’Grady as Mandi | Then

It was no secret that Charlie loved the ladies and was found it difficult to turn any down that came his way. As a result, when Kandi’s mother turned up at Charlie’s house looking for her daughter, Charlie did not turn down the opportunity to have his way with her. Needless to say, Alan wasn’t thrilled when his brother and mother-in-law started spending time together, but it was typical. After all, Kandi and her mother looked more like sisters than mother and daughter.

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Gail O’Grady as Mandi | Then

Gail O’Grady as Mandi | Now

Prior to appearing on Two and a Half Men, Gail O’Grady appeared on television show American Dreams, and after playing Kandi’s mother, Gail took on roles in Ms. Fields and Revenge. As it turns out, her character in Two and a Half Men was not far off from her personality in real life as the actress had been married six times, with her last ending in 2008 from John Stamatakis. However, O’Grady hasn’t given up on love and she is currently dating Chris Beyers.

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Gail O’Grady as Mandi | Now

Paula Marshall as Paula | Then

Alan hadn’t seen much luck in his dating life, so when he met Paula in a nightclub, he thought he had finally met his match. However, Paula dropped a bombshell on Alan and revealed that she used to be a man named Paul, and had a wife named Rachel. Paula later admitted her desire to be in an open relationship leading Alan to date Rachel too. Needless to say, things didn’t end well and the ladies left Alan to go it alone.

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Paula Marshall as Paula | Then

Paula Marshall as Paula | Now

Two and a Half Men was not Paula Marshall’s first rodeo in TV and she has also appeared in House, Law and Order, Murder in the First, Switched at Birth, and The Mentalist. In addition to her work on TV, Marshall also appeared in the movie We Love You, Sally Carmichael! Paula is married to fellow actor Danny Nucci, who is most well-known for appearing in the award-winning iconic James Cameron blockbuster, Titanic, playing Jack’s best friend Fabrizio.

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Paula Marshall as Paula | Now

Tammy Lauren as Shannon | Then

At Judith’s second marriage to Herb, Alan met the beautiful Shannon, but he later found out from Charlie that she was previously engaged to Herb. Both Alan and Shannon were hung up on their exes an attempted to make them jealous by faking an intimate moment at the wedding. Shannon took it one step further and screamed out Alan’s name for all of the guests to hear. Their plan didn’t work and neither won back their ex.

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Tammy Lauren as Shannon | Then

Tammy Lauren as Shannon | Now

Outside of her cameo on Two and a Half Men, Lauren had a permanent role on long-running soap opera, The Young and the Restless, playing detective Maggie Sullivan. Tammy has not had as successful a career as some of the other women who appeared on the sitcom, and her most recent work was on an episode of Criminal Minds in 2014. Outside of acting, Lauren has been married to Israeli actor Guri Weinberg since 1997.

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Tammy Lauren as Shannon | Now

Justine Eyre as Gabrielle | Then

Charlie’s house never seemed to be free of drama, that mostly involved women. When Charlie began dating Gabrielle, Alan discovered that Charlie had stolen Alan’s high school girlfriend and instead of putting things in the past, he set his sights on stealing Gabrielle from Charlie. After his plan of action went swimmingly well, Alan backtracked and decided it was uncomfortable, so broke it off. When he returned home, he found Charlie in bed with the high school girlfriend!

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Justine Eyre as Gabrielle | Then

Justine Eyre as Gabrielle | Now

Justine Eyre’s profile was not increased through her stint on Two and a Half Men, but she has appeared on other TV shows including Mad Men, The Secret Life of the American Teenager, and CSI: Miami. However, Eyre has not appeared in anything since 2016, which makes many people wonder what and if she will she continue acting. It would be surprising if she didn’t stay in the industry considering she is married to screenwriter John Allen Nelson.

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Justine Eyre as Gabrielle | Now

Maggie Lawson as Ms. McMartin | Then

Just because Charlie was killed off the show, it didn’t mean that Alan, Walden, and Jake would stop their flirtatious ways. When Alan and Walden wanted to adopt a child, they took a liking to social worker, Ms. McMartin. When the men were given a child named Louis, McMartin discovered that they had lied about being eligible to adopt but she forgave them and proceeded to date Alan. However, she quickly changed her mind and decided to move on to Walden instead.

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Maggie Lawson as Ms. McMartin | Then

Maggie Lawson as Ms. McMartin | Now

Maggie Lawson had a successful career in acting both before and after appearing in the sitcom Two and a Half Men. She appeared in shows including Psych, Angel From Hell, and The Great Outdoors. In addition, Maggie won the role to play Juliet O’Hara in the film adaptation of Psych, which was released in December 2017. Maggie is married to actor Ben Koldyke, who is famous for his role in the NBC series, Mr. Robinson.

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Maggie Lawson as Ms. McMartin | Now

Conchata Ferrell as Berta | Then

Other than his mother, the other stable woman with no romantic connection in Charlie’s life was of course the housekeeper, Berta. Although Charlie and Berta often butt heads over Berta’s sharp-tongue and cynical attitude, she is the responsible and caring mother figure in the household. Berta was increasingly popular with the fans and producers kept her on when Walden took over from Charlie to be their permanent maid. Berta appeared in every season of the show.

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Conchata Ferrell as Berta | Then

Conchata Ferrell as Berta | Now

After becoming a main character and appearing in all 12 seasons, Berta will always be recognized for her hilarious role in Two and a Half Men. In 2005 and 2007, she was nominated for two Primetime Emmy Awards for Outstanding Supporting Actress in a Comedy Series. Ferrell has also appeared on Broadway in 2011 and in 2015, Conchata appeared in the movie Krampus. Most recently in 2017, she was reunited with ex co-star, Ashton Kutcher, to star in TV series The Ranch. 

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Conchata Ferrell as Berta | Now

Jenny McCarthy as Courtney Leopold | Then

Just because Charlie’s mother was set to marry Courtney’s father, it did not stop him from dating the beautiful blonde. However, Alan saw a different side of Courtney and warned Charlie of her crazy behavior. Courtney managed to convince Charlie to buy her a Ferrari and give her $50,000, but Charlie did not walk away. Unsurprisingly, it all ended abruptly when Charlie found out that Courtney’s real name was Sylvia and her and her fake father were con-artists.

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Jenny McCarthy as Courtney Leopold | Then

Jenny McCarthy as Courtney Leopold | Now

McCarthy got her start long before appearing on Two and a Half Men. She found fame as a Playboy bunny before acting as host on an MTV dating show. Following this, she was given her own self-titled show and found love with actor Jim Carey, but the two were divorced in 2010. Since then, McCarthy married Mark Wahlberg’s brother Donnie and the two have their own reality show. Aside from being an actress and model, Jenny is an author, screenwriter and activist.

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Jenny McCarthy as Courtney Leopold | Now

Teri Hatcher as Liz | Then

Judith’s complicated relationship with Alan got even more twisted when her sister Liz paid them a visit. Liz and Charlie previously got together at Alan and Judith’s wedding, but Charlie did not remember the incident. Liz, however, was over Charlie and instead decided to try and get with Alan, a decision which hurt her sister. It later came out that Alan initially wanted Liz before he began dating Judith. However, when the two ended up in a room together, nothing happened.

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Teri Hatcher as Liz | Then

Teri Hatcher as Liz | Now

Terri Hatcher has had an incredibly successful career in acting. She portrayed Lois Lane on the series Lois & Clark: The New Adventures of Superman, Paris Carver in the James Bond movie Tomorrow Never Dies, and for her leading role in Desperate Housewives, she won a Golden Globe, three SAG awards and a Primetime Emmy nomination. Recently, Hatcher has appeared in The Odd Couple and Supergirl. Hatcher hasn’t been too lucky in love having been married and divorced twice. 

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Teri Hatcher as Liz | Now

Jaime Pressly as Tammy | Then

When Jake introduced his new girlfriend to his father, it showed that the apple doesn’t fall far from the tree. His girlfriend, named Tammy, was the mother of three children and covered in tattoos, as she owned her own parlor. Despite their age gap and different lives, the catalyst for their break up was the fact that Jake had dated Tammy’s daughter, Ashley. In addition, Tammy had also got together with Walden, which complicated things further.

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Jaime Pressly as Tammy | Then

Jaime Pressly as Tammy | Now

Jamie Pressly is a very famous actress in Hollywood and is best known for playing Joy Turner on NBC sitcom My Name Is Earl. She has won one Emmy award and has been nominated for Golden Globes, and SAG awards. Pressly has also starred in a number of movies including  Poison Ivy: The New SeductionJoe DirtThe OogielovesDOA: Dead or Alive, and I Love You, Man. Most recently, she has been starring on CBS sitcom, Mom.

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Jaime Pressly as Tammy | Now

Judy Greer as Bridget Schmidt | Then

Soon after Ashton Kutcher joined Two and a Half Men to take over Charlie’s role, we were introduced to his ex-wife Bridget. Walden took the break-up really hard and Alan found him when he was going to take his own life because of it. Apparently, Bridget found Walden too immature to stay married to but when Walden started dating Zoey, everything changed. Bridget came running back to Walden to get back together.

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Judy Greer as Bridget Schmidt | Then

Judy Greer as Bridget Schmidt | Now

Judy Greer is somewhat of a triple threat and is not just a talented actress. She has appeared in films including What Women WantThe Wedding Planner13 Going on 3027 Dresses and Love & Other Drugs. In addition, she took a position behind the cameras and was the casting director for the Entourage movie. She became a regular feature in Two and a Half Men, playing Walden’s ex-wife and in 2014, she released her first book, I Don’t Know What You Know Me From: Confessions of a Co-Star. 

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Judy Greer as Bridget Schmidt | Now

Sophie Winkleman as Zoey Hyde-Tottingham-Pierce | Then

The woman who changed Walden’s attitude about getting back with his ex-wife was Zoey. The British beauty stole Walden’s heart and he became infatuated with her rather quickly. However, everything came crashing down two years later when she declined his marriage proposal. It was later discovered that Zoey had been dating another man during her time with Walden. As an act of revenge, Walden bought Zoey’s daughter a vicious dog for her birthday.

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Sophie Winkleman as Zoey Hyde-Tottingham-Pierce | Then

Sophie Winkleman as Zoey Hyde-Tottingham-Pierce | Now

Sophie Winkleman is perhaps one of the highest class cast members as she married English royal Lord Frederick Windsor, who is a cousin of Queen Elizabeth. Despite being a part of the British royal family, she continued to pursue a career in acting and is currently filming a new TV show titled Thrust, which is set for release in 2018. She has also appeared in  CSI: Miami in 2011 and  Milo Murphy’s Law in 2016.

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Sophie Winkleman as Zoey Hyde-Tottingham-Pierce | Now

Diora Baird as Wanda | Then

Baird took on the part of Wanda on one episode on Two and a Half Men, but she made quite the impression with her stunning looks. Baird got her start in showbiz as a model for notable brand Guess and went on to work with the likes of Playboy, which unsurprisingly earned her much more attention. In her career on screen, Baird has also starred in romantic comedy Wedding Crashers which starred Owen Wilson and Vince Vaughn.

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Diora Baird as Wanda | Then

Diora Baird as Wanda | Now

Since her short stint on Two And A Half Men, Baird has starred in a couple of funny videos with website Funny Or Die and in 2014, she played a large role in film Beautiful Girl as an adult film actress. In addition, she had a recurring role in Cocked on Amazon alongside Brian Dennehy, Jason Lee, Dreama Walker, and Sam Trammell. Outside of acting, Baird opened up about dating female comedian Mav Viola.

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Diora Baird as Wanda | Now

Krista Allen as Olivia Pearson | Then

Things went from bad to worse for Charlie when he turned up at his mother’s house for a dinner with her boyfriend and his daughter, Olivia. As it turns out, Olivia and Charlie had previously dated and it didn’t end well for them. The dinner got incredibly uncomfortable and drinks started going flying. As if things could not have got more awkward, Evelyn was on the receiving end of being dumped, as her boyfriend left her for a younger woman.

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Krista Allen as Olivia Pearson | Then

Krista Allen as Olivia Pearson | Now

Krista Allen had a successful career which started back in the 90s. She started out with a role on long running soap opera Days of Our Lives which has been running for an impressive 53 seasons. Moreover, she has also taken on parts in the original Baywatch, as well as the feature film The Final Destination and Anger Management. Allen was recently cast in the movie Best Mom as well as the comedy Eleven Eleven.

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Krista Allen as Olivia Pearson | Now

Kelly Stables as Melissa | Then

There has been a recurring theme in Two and a Half Men and many of the women dated both Charlie and Alan. This was no different for Alan’s secretary, Melissa, who started to date Charlie before switching to Alan. However, Alan once again lied about his lifestyle and his relationship with Melissa was still going on when he was living with Lyndsey. Th relationship became complicated when Melissa asked Alan for a raise and health insurance, leading him to end everything via text.

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Kelly Stables as Melissa | Then

Kelly Stables as Melissa | Now

Following her appearance on Two and a Half Men, Kelly Stables stayed in acting and lent her voice to animated show, W.I.T.C.H, in the character of Will Vandom, as well as appearing in Superstore and Malibu Dan the Family Man. In addition, Kelly has appeared in films such as Horrible Bosses 2 and had a voice role in Cloudy with a Chance of Meatballs 2. In 2016, Stables was cast in The CW’No Tomorrow as a recurring cast member.

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Kelly Stables as Melissa | Now

Heather Locklear as Laura | Then

Charlie hasn’t always had the best of taste when it comes to picking women, and going for Laura was a bad idea. She was Alan’s lawyer during his divorce from Judith but things turned sour when Charlie promised her that he would be there for her whenever she wanted, something that was broken very quickly. Laura decided to seek revenge and she took it out on Alan when she ruined the divorce settlement between him and Judith, resulting in him finding a new lawyer.

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Heather Locklear as Laura | Then

Heather Locklear as Laura | Now

Heather Locklear was was one of the most famous actresses in the 80s and 90s, most commonly known for her roles on Melrose Place and Spin City. Outside of her successful career, Heather has managed to be a constant feature in the tabloids due to her health issues and her very public and bitter divorce. Nowadays, Heather has taken on roles in Franklin & Bash as well as Too Close to Home and Fresh Off The Boat.

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Heather Locklear as Laura | Now

Kimberly Quinn as Donna | Then

Donna and Alan seemed to really hit it off on their double date. The couple continued to date until Alan decided he was bored and wanted to end everything. He went to Charlie for advice on how to cut things off, as his brother was increasingly used to this. After following Charlie’s instructions and letting her down easily, Alan was able to breathe a sigh of relief, but the same couldn’t be said for Linda. She didn’t take it well to say the least.

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Kimberly Quinn as Donna | Then

Kimberly Quinn as Donna | Now

Quinn is most commonly known for her role as Gretchen on the FX television series Terriers, as well as her role as Tess Masterson on the ABC Family series Twisted. In addition, Quinn has made cameos in a number of notable series including Suddenly SusanNash BridgesDiagnosis: MurderNYPD BlueWithout a TraceHouse M.D., and CSI: NY. Quinn is married to producer Theodore Melfi and the couple worked together on the movie St. Vincent.

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Kimberly Quinn as Donna | Now

Denise Richards as Lisa | Then

Lisa was one of the few women who Charlie called his girlfriend and actually lived in his home. When things became serious, Charlie the commitment-phobe panicked and broke up with Lisa. However, Lisa later got married to someone else but promised to call Charlie if she got divorced–talk about cursing the marriage before it began! Unsurprisingly, Lisa got divorced and went back to Charlie who tried hard, but not enough to take care of her and her child. Their relationship ended once again.

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Denise Richards as Lisa | Then

Denise Richards as Lisa | Now

Lisa was played by none other than Charlie Sheen’s wife Denise Richards, so the chemistry between them was real. They were married between 2002 until 2006 and had two daughters together, but once they split, everything got very messy. At one point, they agreed to be civil for the sake of their family, but things spiraled when Charlie battled his addiction demons. After nasty accusations, lawsuits went flying, but things calmed after a couple years. Richards is also a successful actress in her own right.

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Denise Richards as Lisa | Now

Kristin Dattilo as Cindy | Then

Charlie managed to charm many women into the bedroom, but one person who wasn’t fooled by his tricks was Cindy. Someone who enjoyed having her in the house however, was Jake, who decided to use some of her best assets to recreate for an art project. In an unlikely twist, Judith meets Cindy and the two create a strong bond over their troubled relationships with their fathers. Alan was suspicious of this and began thinking that the two were actually dating.

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Kristin Dattilo as Cindy | Then

Kristin Dattilo as Cindy | Now

Kristin got her start in acting after playing Yola Gaylen on The Chris Isaak Show from 2001 until 2004. Aside from this, she has also taken up appearances in TV shows including CSI, Dexter, Beverly Hills, 90210, Friends, Grounded for Life, and Veronica Mars. Dattilo can also be recognized through her appearance in the music video of Aerosmith’s 1989 record “Janie’s Got a Gun”. She has been married to screenwriter Jason Keller since 2005, the couple have two children together.

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Kristin Dattilo as Cindy | Now

Courtney Thorne-Smith as Lyndsey McElroy | Then

Lyndsey played a large part in season seven on the show, playing Alan’s love interest. Throughout the season, they were on-again, off-again and most people forgot how many times they broke up and got back together. Their relationship was founded after Jake befriended Lyndsey’s son, and it safe to say that Alan was thrilled when he met the mother. Unfortunately, Lyndsey’s drinking played a big part in their break up and she moved on to Walden, which became problematic.

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Courtney Thorne-Smith as Lyndsey McElroy | Then

Courtney Thorne-Smith as Lyndsey McElroy | Now

Courtney Thorne-Smith played Alan’s girlfriend Lyndsey McElroy on the successful sitcom for five years, but prior to this, she took on a role in Ally McBeal between 1997-2002. Since then she has slowed down her acting jobs to focus on her son and husband. After taking a short break, Smith returned to appear in ABC’s new comedy series, Fresh Off The Boat while also taking on animates series roles and lending her voice to Robot Chicken.

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Courtney Thorne-Smith as Lyndsey McElroy | Now

April Bowlby as Kandi | Then

It came as a shock when she ended up marrying Alan in Vegas and moved in with him. Unfortunately, it all came crashing down when Kandi landed a part in the show Stiffs, forcing her to leave Alan.

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April Bowlby as Kandi | Then

April Bowlby as Kandi | Now

After leaving Two and a Half Men, April Bowlby continued to make a name for herself in acting, but this time, she shunned the red head and went blonde. April went on to appear in hit shows including The Big Bang Theory, How I Met Your Mother, and Drop Dead Diva. In addition to TV, April transitioned over to the big screen and is currently filming the movie Love Me or Else alongside Cindy Busby and Jon Prescott.

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April Bowlby as Kandi | Now

Missi Pyle as Miss Pasternak | Then

When Charlie started dating Miss Pasternak, it worked out in everyones favor as she started giving Jake good grades. Things went from bad to worse for the teacher when she later revealed she was banned from teaching and was dancing for a living now.

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Missi Pyle as Miss Pasternak | Then

Missi Pyle as Miss Pasternak | Now

Pyle has had a very successful acting career and has appeared on many TV shows including  Mad About YouFriendsHeroesTwo and a Half MenFrasierMy Name Is Earl2 Broke GirlsJennifer Falls, and Mom. In addition to acting, Pyle has a passion for music and is one half of country-rock band Smith & Pyle. The actress has been married and divorced twice and is not looking to go for a third time.

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Missi Pyle as Miss Pasternak | Now

Brooke Shields as Danielle Stewart | Then

Charlie comes up with a plan and introduces Alan to Danielle in an attempt to get him to find his own house. Charlie was well aware of Danielle’s past and thought Alan was the man she should settle for. However, after the two ended up having a heart to heart, Charlie decided that Danielle was better off with him and the brothers ended up fighting over her. In a turn of events, Alan and Charlie stuck together and kicked Danielle out.

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Brooke Shields as Danielle Stewart | Then

Brooke Shields as Danielle Stewart | Now

Brooke Shields had been acting long before Two and a Half Men after starting out as a child star, taking on modeling and commercials. Shields is now well into her 50’s and has starred in TV shows including Law & Order: Criminal Intent, The Middle, and Hannah Montana just to name a fewIn 2017, Shields reprised her recurring role in Law and Order: Special Victims Unit starting in Season 19. She is married to Chris Henchy and the couple have two children.

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Brooke Shields as Danielle Stewart | Now