The show may have the title Two and a Half Men, but many lovely women have graced the series over the years. After all, the show ran for twelve seasons. Keep reading to see what the ladies who played our favorite female characters are now up to.
Missi Pyle Then
On the show, Missi Pyle portrayed Miss Pasternak, who starts going out with Charlie. At first, their relationship results in Jake starting to get good grades! Things go downhill, though. The teacher reveals that she was banned from teaching and she had to start dancing so she could pay the bills!
Missi Pyle Now
Missi Pyle has had a great acting career. Some of the TV shows that she has been on are My Name is Earl, Mad About You, Two Broke Girls, Mom, and Friends. Aside from acting, her other passion is music. As a matter of fact, she was one-half of the country-rock duo Smith & Pyle, the other half being actress Shawnee Smith. Pyle has been married and divorced two times over the years.
Marin Hinkle Then
Marin Hinkle appeared on the show regularly since she portrayed Judith, Alan’s ex-wife. The two have a weird relationship but they try their best when it comes to co-parenting Jake. They do often get into arguments about child support and alimony. Alan often calls Judith out for using the money on cosmetic surgery and luxury goods. Things get even more complicated when she falls for Jake’s doctor, but their marriage ends in divorce after she learns that he was cheating.
Marin Hinkle Now
When the show wrapped up, Marin Hinkle went on to do other acting projects. For example, she was cast in Madam Secretary. She was also on Speechless and Homeland. In terms of the big screen, she has also done several movies. Before/During/After was one of her more recent film projects. She may have played a psycho ex on Two and a Half Men, but Marin Hinkle is happily married to Randall Sommer.
Emmanuelle Vaugier Then
Once Charlie has his eyes set on a woman, he becomes a man with a mission and he won’t stop until he succeeds. This is what happened after he meets Emmanuelle Vaugier’s character Mia, a dance teacher. He makes Jake dance to get closer to Mia. In fact, Charlie even agrees to her conditions so that he could date her. He agrees to give up smoking, drinking, and even meat. However, Charlie continues to do these things behind her back, so she ends up leaving him.
Emmanuelle Vaugier Now
After her stint on Two and a Half Men, Vaugier’s career took off. She appeared on other TV shows, such as Mistresses, Lost Girl, Rogue, and One Tree Hill. Aside from that, she snagged a spot on Maxim’s “Hot 100 List.” She also worked on movies, like Destruction Los Angeles and Washed Away. Her more recent work includes the thriller Masks Don’t Lie. It is set and was filmed in Venice.
Holland Taylor Then
A constant part of both Charlie and Alan’s life is their mother, who was played by Holland Taylor. The brothers have a complicated relationship with their mother, Evelyn, though she is one of the few female characters who could give her sons a piece of her mind. She may have a reputation for her gold-digging ways and for dating older men, but the viewers loved her. Charlie and Alan are unfortunately not as fond of Evelyn as the fans were.
Holland Taylor Now
The amazing Holland Taylor is one of the very recognizable faces in the entertainment industry. Since the ‘80s, she has been famous and was even nominated for Best Supporting Actress four times for her portrayal of Evelyn on Two and a Half Men! You probably spotted her in the popular film Legally Blonde (2001). She is now working on the show Mr. Mercedes, which is based on Stephen King’s novel.
Melanie Lynskey Then
Who can forget Rose, a woman who ends up getting obsessed with Charlie after they spend the night together? Played by Melanie Lynskey, Rose does not take no for an answer. She even stalks him! Eventually, things do turn around. Charlie agrees to marry her in the end before the two run off to Paris. However, this was just too good to be true. Before they can get married, he dies.
Melanie Lynskey Now
The brunette bombshell has been part of films like Coyote Ugly, Sweet Home Alabama, and Heavenly Creatures. However, her leading roles came later, in projects like Hello I Must Be Going, I Don’t Feel At Home In This World Anymore, Happy Christmas, and The Intervention. Her marriage to Jimmi Simpson lasted from 2007 until 2014. She is currently engaged to Jason Ritter and they welcomed a baby girl in 2019.
Jennifer Taylor Then
Anyone who has followed the show probably remembers Jennifer Taylor’s character, Chelsea Melini. Although she starts out as one of Charlie’s one-night stands, their relationship soon evolves into something deeper. In fact, she is the first person Charlie professes his love to. It is the first time that he wears his heart on his sleeves, and they even get engaged. Sadly, she gets tired of him in the end and leaves him. She ends up dating the lawyer who is working for Alan.
Jennifer Taylor Now
At first, the writers did not plan for Chelsea Melini to steal Charlie’s heart. However, after her initial appearance on the show, she appeared more and more frequently. Jennifer Taylor continued to act when she left Two and a Half Men. She has appeared in other shows, such as NCIS, Shameless, and Mom. She married the songwriter Paul Taylor and they are parents to two kids – a daughter and a son.
Allison Janney Then
Alan and Beverly meet on a dating site. Hoping to impress her, he lies and claims that he is the owner of the house. However, he feels guilty when she starts opening up to him and talking about her former marriages. After he comes clean, she does not appear to mind. The two stay together but Charlie walks in on them. He sees Beverly in the middle of tying Alan up!
Allison Janney Now
This actress has definitely made her mark in Hollywood. Even before Allison Janney appeared on the show, she had already worked on various projects, including starring in The West Wing from 1999 to 2006. She has also done feature films and has appeared in Juno, Hairspray, and The Girl on the Train. Nowadays, she is busy on the CBS sitcom Mom. Anna Faris used to play her daughter on the show but has left the series.
Jeri Ryan Then
When Sherri (played by Jeri Ryan) is introduced, Charlie thinks that he has finally found his match. The usual tricks which he pulls on women somehow do not work on her. Charlie initially finds her attitude attractive, but he eventually tires of the fact that she is always one step ahead of him. The two eventually break things off, though she tries her luck with Alan first! Of course, she does not succeed.
Jeri Ryan Now
The lovely Jeri Ryan’s big break came when she played Seven of Nine, a former borg drone, on the TV series Star Trek: Voyager. She also worked on other projects including Body of Proof, Major Crimes and Law & Order: Special Victims Unit. She was married to politician Jack Ryan. However, they split up due to conflicting schedules. She has remarried and now share two kids with her husband Christophe Eme.
Kimberly Williams-Paisley Then
Alan starts dating Kimberly Williams-Paisley’s character, Gretchen Martin, Larry’s sister. However, he also does not tell her the truth and says that he owns the apartment. He tells her that he does not live with his brother. As the lies pile up, they become too much for Alan to keep track of. After learning about his deception, Gretchen dumps him and tells him that her ex-husband was a pathological liar. She does not want to deal with that ever again.
Kimberly Williams-Paisley Now
The radiant actress has been acting since she was little. One of her notable works is the film Father of the Bride. Aside from that, Kimberly Williams-Paisley was also on the sitcom According to Jim for eight years and worked on the ABC drama Nashville. Recently, she was in the films Darrow and Darrow and The Christmas Train. In 2003, she tied the knot with the country musician Braid Paisley.
Ming-Na Wen Then
Charlie meets Linda when he agrees to go on a double date with Alan. Charlie is immediately attracted to Linda, but turns him down since she can see through him. She rejects him multiple times, but the situation changes after Charlie gets a DUI. He is surprised when he sees that she is the judge! After this, she gives him a shot, but their little romance only goes on for a short while.
Ming-Na Wen Now
Ming-Na Wen was not a Hollywood newcomer, but she did not appear in front of the camera a lot. She voiced the eponymous character in Disney’s Mulan films. She has also lent her voice to other films, such as Ralph Breaks the Internet: Wreck-it Ralph 2 and Sofia the First. When it comes to her appearances on TV, she was on SGU: Stargate Universe and Eureka. She is currently working on the ABC series Agents of S.H.I.E.L.D.
Gail O’Grady Then
Charlie’s love for the ladies is basically a given and he struggles to turn down any whom he comes across, so he pursues Mandi, portrayed by Gail O’Grady. Mandi has been looking for her daughter Kandi. We can totally see it as Mandi and Kandi do not really look like mom and daughter. They look more like sisters. Of course, Alan is not happy with the idea that his own brother is making a move on his mother-in-law.
Gail O’Grady Now
Aside from her appearance on the show, Gail O’Grady has also been on Revenge, American Dreams, and Ms. Fields. It turns out that her character on Two and a Half Men is not that different from her. After all, she has been married six times. Her last marriage was with John Stamatakis but it ended in 2008. However, it seems she has not closed her doors on romance. We hope she finally finds the one!
Paula Marshall Then
Alan is not really the luckiest when it comes to the dating department. This is why he assumes that he struck gold when he meets Paula Marshall’s character Paula in a nightclub, but she later tells him that she used to be a married man named Paul. Later on, she tells Alan that she is looking for an open relationship and even urges him to date her wife too! As you can imagine, things do not go well for anyone involved in this.
Paula Marshall Now
Two and a Half Men was not Paula Marshall’s debut show. She has appeared in other things including Murder in the First, House, Switched at Birth and The Mentalist. Aside from that, she co-starred on the shows Cupid and Gary Unmarried. She has also worked on the film We Love You, Sally Carmichael. Back in 2003, she tied the knot with Danny Nucci, who portrayed Fabrizio in Titanic. They have one child together.
Tammy Lauren Then
Tammy Lauren portrayed Shannon, whom Alan meets during Judith and Herb’s second wedding. However, Alan later finds out that Herb and Shannon were once engaged! Both still hung up on their exes, Alan and Shannon use each other in order to make their exes jealous at the ceremony. Taking it a step further, Shannon screams Alan’s name out during the wedding. However, their plan does not work and neither of them succeeds in winning back their ex.
Tammy Lauren Now
Aside from her cameo on Two and a Half Men, Lauren played Maggie Sullivan on the soap opera The Young and the Restless for quite some time. Unfortunately, her acting career has not been as successful as those of the others on this list. In fact, her most recent work was an appearance in one episode of Criminal Minds in 2014! However, her personal life seems to be doing just fine as she has been married since 1997. Her husband, Guri Weinberg, is an Israeli actor.
Justine Eyre Then
If there is one thing you learn from watching the show, it is that there is always drama in Charlie’s house. When Charlie starts dating Gabrielle, Alan learns that his brother once stole his girlfriend in high school. This is why Alan tries to steal Gabrielle! Even though the situation is going well, he finds it uncomfortable and ends up backpedaling. When he goes back home, he find his brother cozying up with his high school sweetheart again.
Justine Eyre Now
After her stint on Two and a Half Men, Justine Eyre has not been really active in Hollywood. However, she was on CSI: Miami, Mad Men, and The Secret Life of the American Teenager. Her last acting credit was from 2016. She has narrated almost one hundred books, though. She is also a recipient of the prestigious Audie Award. She is married to screenwriter John Allen Nelson and they have one son together.
Maggie Lawson Then
Charlie is killed off, but Alan, Jake, and Walden continue their flirtatious ways. When Alan and Walden decide to adopt, they meet the social worker and end up liking her. When the two are assigned Louis, Ms. McMartin (played by Maggie Lawson) realizes that Alan and Walden lied about their application. She ends up forgiving them, though, and even dates Alan. However, she changes her mind in the end. She moves on and dates Walden.
Maggie Lawson Now
Even before Maggie Lawson appeared on the show, she already had an amazing career. Over the years, the actress has appeared on other shows, such as Psych, Angel From Hell, and The Great Indoors. Aside from that, she also reprised her role of Juliet O’Hara in the movie adaptation of Psych in 2017. She tied the knot with Mr. Robinson star Ben Koldyke in 2015, but they got divorced two years later.
Conchata Ferrell Then
Aside from his mother, the other constant female character in Charlie’s life is probably Berta. Charlie and Berta may often argue over her sharp tongue and cynicism, but she is like a mother figure in the house. Conchata Ferrell’s character was popular among fans, so producers had her stay on even after Charlie is killed off. Fun fact: Berta has appeared in every season of Two and a Half Men.
Conchata Ferrell Now
The talented Conchata Ferrell will probably be most remembered for playing Berta. She received Primetime Emmy nominations for Outstanding Supporting Actress in a Comedy Series twice. She had gone on Broadway as well. Among her most recent work was appearing on the TV show The Ranch, which reunited her with Ashton Kutcher. She passed away at the age of 77 in October of 2020 due to complications from a cardiac arrest.
Jenny McCarthy Then
His mother is getting married to her dad, but that does not stop Charlie from dating the blonde bombshell Courtney (played by Jenny McCarthy). However, Alan knows Courtney’s true nature and warns Charlie about her behavior. She succeeds in getting Charlie to give her a Ferrari and $50,000, but he still does not walk away. Things end between them after Charlie finds out that Courtney and her fake dad were con artists.
Jenny McCarthy Now
Jenny McCarthy was already quite a big star even before she appeared on the sitcom. She hosted an MTV dating show and was a Playboy bunny. Aside from that, she had a self-titled show. She was once married to Jim Carrey but in 2010, they got a divorce. She is now happily married to Blue Bloods actor Donnie Wahlberg. On top of acting, she is also an author, screenwriter, and activist.
Teri Hatcher Then
Judith and Alan already have a complicated relationship but it gets worse when her sister, Liz, drops by. Teri Hatcher’s character, Liz, and Charlie hooked up at the wedding, but he does not remember the incident. Liz is over him, though, and she tries to get with Alan. Obviously, this hurts her sister. It is later revealed that Alan had initially wanted to date Liz before he started going out with Judith. Nothing happens between Alan and Liz, though. Whew!
Teri Hatcher Now
Terri Hatcher has had great success in Hollywood. She has been on Lois & Clark: The New Adventures of Superman, Desperate Housewives, and Tomorrow Never Dies. Her performance on Desperate Housewives even earned her three SAGs, a Golden Globe, and a Primetime Emmy nomination. Recently, the actress was on The Odd Couple and Supergirl. Sadly, she has not been quite lucky in her love life. However, she does have a daughter.
Jaime Pressly Then
It is clear that Jake is a chip off the old block when he brings his girlfriend to meet his dad. Tammy (portrayed by Jaime Pressly) is a mom of three and runs a tattoo parlor. In spite of their huge age gap and different backgrounds, the reason that they break up is Jake dating her daughter, Ashley. Aside from that, Tammy also gets together with Walden. We do not really need to explain how messy this was, do we?
Jaime Pressly Now
A big Hollywood actress, Jammie Pressly is best known for her character Joy Turner on My Name Is Earl. She has been nominated for a Golden Globe and an Emmy over the years. She has also worked on several films like Poison Ivy: The New Seduction, I Love You, Man, DOA: Dead or Alive, Joe Dirt, and Not Another Teen Movie. She was on the show I Hate My Teenage Daughter and recently appeared on Mom as well.
Judy Greer Then
After Charlie is killed off, Ashton Kutcher’s character Walden is introduced. After his separation with his then-wife, Walden has a tough time and Alan finds him as he was trying to take his life. Judy Greer’s character, Bridget, apparently thought he is too immature, but when he starts dating Zoey, Bridget tries to get him back. He tells Bridget that he has moved on. In anger, she runs her car into the beach house.
Judy Greer Now
The incredibly talented Judy Greer has appeared in a variety of films, such as 27 Dresses, The Wedding Planner, 13 Going on 30, Love & Other Drugs, and What Women Want. She also had a starring voice role on the animated comedy series Archer, directed the comedy drama A Happening of Monumental Proportions, and released a book titled “I Don’t Know What You Know Me From: Confessions of a Co-Star.”
Sophie Winkleman Then
Played by Sophie Winkleman, Zoey steals Walden’s heart in no time and changes his desire to get Bridget back. He even asks Zoey to marry him but she turns him down. After this, everything comes crashing down. Walden eventually finds out that Zoey was going out with someone else while they were together. To get revenge on her, he gifts her daughter a vicious dog for the little girl’s birthday.
Sophie Winkleman Now
Perhaps one of the show’s fanciest cast members, the gorgeous Sophie Winkleman is married to one of the Queen’s cousins, Lord Frederick Windsor. She may be part of the British Royal family, but she continues to act. In 2018, she appeared on the FX show Trust, which is about the Getty kidnapping. You might have seen her on CSI: Miami as well. She also lent her voice to the Disney animated series Milo Murphy’s Law.
Diora Baird Then
Diora Baird was on the show for just one episode, but she was definitely memorable due to her good looks. She played Charlie’s ex-girlfriend Wanda, who is a model. Jake even has a poster of her in his room. Diora Baird actually started her career by modeling for Guess. She later posed for Playboy, receiving more attention. You might remember seeing her in the 2005 comedy Wedding Crashers as well.
Diora Baird Now
After her brief stint on the show, Diora Baird appeared in a number of funny videos on the website Funny or Die and played an adult film star in the 2014 movie The Ugly Life of a Beautiful Girl. She was also on the Amazon series Cocked, where she played a recurring character. The actress was once married to Jonathan Togo, whom she shares a child with. In 2017, she shared that she was dating female comedian Mav Viola.
Krista Allen Then
Charlie’s mom hosts a dinner party and he attends. However, things go downhill after he finds out that his mother’s new boyfriend is Olivia’s father. Charlie once dated Olivia (portrayed by Krista Allen). Let us just say things did not end too well between them. Needless to say, it was an uncomfortable dinner. Charlie and Olivia get into a heated discussion and she throws her drink in his face. To make things worse, Evelyn’s boyfriend dumps her for someone younger!
Krista Allen Now
The actress has had a pretty successful acting career since she started in the ‘90s. She got her start through the soap opera Days of Our Lives. She also appeared on Baywatch and in films like Anger Management and Final Destination. Her most recent work include the 2018 films Eleven Eleven and Best Mom. She has been married twice but both ended in divorce. She has one son from her first marriage.
Kelly Stables Then
Have you noticed that a number of female characters on the show dated both Charlie and Alan? This is the case for Alan’s secretary Melissa, played by Kelly Stables. She dates Charlie first but later gets with Alan. Once more, Alan lies about his life. He dates Melissa while he lives together with Lyndsey! Unfortunately, Melissa and Alan’s relationship gets complicated after she asks him for a raise and health insurance.
Kelly Stables Now
After Kelly Stables appeared on Two and a Half Men, she continued to work in the entertainment industry. She has worked on Superstore, The Exes, Malibu Dan the Family Man, No Tomorrow, and the film Horrible Bosses 2. Aside from that, she was also a voice actor for Cloudy with a Chance of Meatballs and W.I.T.C.H. She has been married to Kurt Patino since 2005 and they share a son together.
Heather Locklear Then
Let us just say that Charlie is not the best when it comes to picking out the ladies. This explains why he pursues Heather Locklear’s character Laura, who is Alan’s divorce lawyer. Things go south after Charlie breaks his promise of being there for her when she needs him. As revenge, she ruins Alan’s divorce settlement, making him go looking for a new lawyer. To be honest, Alan should have seen this coming.
Heather Locklear Now
From the ‘80s to the ‘90s, Heather Locklear was one of the biggest stars. She is best known for co-starring on the popular shows Melrose Place and Spin City. She was also nominated for four Golden Globes. Unfortunately, the actress used to be featured on tabloids regularly because of her health problems and public divorce. Her more recent projects include Fresh Off The Boat, Too Close To Home, and Franklin & Bash.
Kimberly Quinn Then
Alan and Donna (portrayed by Kimberly Quinn) get along really well during their double date with Charlie and Donna’s friend Linda. They continued to date until he becomes bored of her. Alan feels like there is no more spark between them, so he asks Charlie for advice. Alan receives instructions to let Donna down easily. Finally, Alan can breathe a sigh of relief. However, the same cannot be said for her.
Kimberly Quinn Now
Best known for portraying Gretchen on the FX show Terriers and Tess Masterson on ABC’s Twisted, the actress has had appearances on Suddenly Susan, Nash Bridges, Diagnosis: Murder, NYPD Blue, CSI: NY, and Without A Trace. Kimberly Quinn is married to producer Theodore Melfi, who was a writer, producer, and director for the 2016 film Hidden Figures. She also co-wrote the Academy-Award nominated screenplay of the film. The couple owns the production company Goldenlight Films
Denise Richards Then
Charlie does not call many women his girlfriend. Lisa, played by Denise Richards, is among the lucky few. There is even a time when she lives in his house! He panics when they get serious and breaks up with her. She later gets married to another guy and promises to call Charlies in case they divorce. When she does get divorced, it is not really a surprise. She goes back to Charlie but they end up calling it quits once more.
Denise Richards Now
Denise Richards was married to Charlie Sheen in real life at the time, so it is no wonder that they had real chemistry. The couple was together from 2002 to 2006. They share two daughters together. However, after their divorce, things turned very messy. They both tried to be civil for the sake of their daughters, but things got difficult during the time Charlie struggled with addiction. After accusations and lawsuits, things finally calmed between them.
Kristin Dattilo Then
Anyone who has watched Two and a Half Men knows how easy it is for Charlie to charm a woman into his bed. However, Kristin Dattilo’s character Cindy is not fooled by his act. Jake also likes having her around. He even has a crush on her! Judith meets Cindy and the two form a bond owing to their daddy issues. Alan gets suspicious of their relationship and even wonders whether Judith and Cindy were dating.
Kristin Dattilo Now
The gorgeous actress got her start on The Chris Isaak Show, where she spent four years playing the manager Yola Galen. She also had appearances on other shows including Beverly Hills 90210, Grounded for Life, CSI, Dexter, and Veronica Mars. You might remember seeing her in an Aerosmith music video. She was featured in the video for the song “Janie’s Got a Gun.” In 2005, she married Jason Keller and they have two kids together.
Courtney Thorne-Smith Then
In the seventh season of the show, Courtney Thorne-Smith’s character Lyndsey has a big part in the story. She is Alan’s love interest but they have an on-again-off-again relationship. We understand if you have forgotten how many times the two split and made up. Their relationship begins when Jake becomes friends with her son. Sadly, she suffers from a drinking problem. She even tries to make a move on Walden.
Courtney Thorne-Smith Now
Courtney Thorne-Smith played Lyndsey McElroy for five years. Prior to that, she was on Ally McBeal, playing Georgia Thomas. He stint lasted from 1997 to 2002. She also worked on Melrose Place, where she portrayed Alison Parker, and According to Jim. Place Since she decided to focus on her family, her acting career has slowed down. However, she has made her comeback and worked on Robot Chicken and Fresh Off The Boat.
April Bowlby Then
When Alan married Kandi in Vegas, it was quite a shock for everyone. April Bowlby’s character Kandi actually goes out with Charlie first, but after he dumps her, she ends up getting with Alan. After getting married, Alan and Kandi move in together. However, things start falling apart when she lands an acting job on the TV show Stiffs. She leaves him and they get divorced. However, they became friends afterwards.
April Bowlby Now
After her stint on Two and a Half Men, April Bowlby continued to act. She decided to changer her hair color and go blonde. She was on Drop Dead Diva, playing Stacy Barrett, and appeared on shows like The Big Bang Theory and How I Met Your Mother. Aside from TV, she did some movies as well, such as Love Me Or Else. She is currently working on the series Doom Patrol.
Brooke Shields Then
Charlie schemes to introduce Danielle to Alan, hoping to get his brother out of the house. Knowing about her past, Charlie thinks that it is a good idea for her to settle for Alan. However, after having a conversation with her, Charlie realizes that he and Danielle make a better couple. The brothers fight about this. They end up deciding to kick her out, choosing to stick by each other instead.
Brooke Shields Now
Danielle Stewart was played by Brooke Shields, who was a child star. Before the actress got her big break, she did commercials and some modeling. Now in her fifties, Brooke Shields has appeared in many projects like Law & Order: Criminal Intent, The Middle, and Hannah Montana. She played a recurring role on Law and Order: Special Victims Unit. She has been married to Chris Henchy since 2001. She is a mother of two.