Two and a Half Men was arguably one of the most popular American sitcoms ever made. The show managed to last for 12 seasons from 2003-2015. The series made headlines after the main character Charlie Harper, played by Charlie Sheen, left the show after the actor had a feud with the executive producer. Although many thought it would mean an end to series, they were wrong and the lovable Ashton Kutcher came to replace him.
Throughout the 12 years of production, there were hundreds of female characters. Charlie, Alan and Walden each had numerous girlfriends, but Charlie’s list was definitely the longest. Of course, Charlie was not the best or most faithful boyfriend. In the scene of Charlie’s funeral, all 50 of his past lovers showed up, only because they were hoping to ‘spit on the body.’
Although the show’s main characters are of course, the two (and a half) men, it wouldn’t have been the same without the multiple female characters who came in and out of the beach house. A show solely about two brothers would have quickly gone dull without the women of the show. The series was truly driven by the female stars, who helped create moments of comedy, drama and sometimes a bit of insanity. The two brother’s relationships with the women in the series helped the audience get a better understanding of the many layers of Alan and Charlie. They helped us see them at their best, and their worst… but usually the latter.
If it weren’t for the ladies, then who would have been there to put Alan and Charlie in their place?
If you are wondering where the many women of Two and a Half Men are today, then look no further. Keep reading to find out what your favorite TAAHM girls are up to…
Emmanuelle Vaugier as Mia – Then
Mia, a dance teacher, wasn’t interested in Charlie until he said that his nephew Jake enjoyed dancing. Mia agrees to date him as long as he quits smoking, alcohol and eating meat, but Charlie does it anyway behind her back. She found out and left him. Later, she came back and asked Charlie for his sperm so that she could have a baby, Charlie proposes to her instead and the couple go with Alan and Kandi to Vegas to get hitched. Right before they say ‘I do’ Mia asks Charlie when Alan is moving out, he said he isn’t and Mia leaves him. Charlie then gives the ring to Alan and Kandi.
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Emmanuelle Vaugier as Mia – Now
After her recurring role in Two and a Half Men, Emmanuelle Vaugier continued to land multiple roles in movies and television. She played Niko on the abc show Mistresses, and played Evony in the sci-fi series Lost Girl. Most recently, the now 41-year-old was seen in the TV movies Washed Away and Destruction Los Angeles. She is currently working on a mystery thriller film called Masks Don’t Lie.
Denise Richards as Lisa – Then
Charlie and Lisa lived together before Alan moved in but they ended things because Charlie didn’t want a committed relationship. Later on, Lisa tells Charlie that she is getting married and he invites her back to his house and pretends to have become a true family man, in hopes that she will come back to him. Lisa and her husband eventually gets a divorce and she gives Charlie a second chance. In the end, he breaks up with her because she has “commitment issues” when really it was the other way around.
Denise Richards as Lisa – Now
Denise was married to her costar Charlie Sheen from 2002 to 2006. In 2004, the couple welcomed their first child, a daughter named Sam. Only one year later, they welcomed their second daughter, named Lola. The couple divorced in 2006, but they still spend time together with their two girls, who are now 13 and 12. In 2012, Denise adopted a baby girl named Eloise Joni. The now 46-year-old movie star is still going strong with her acting career, and just finished filming for a comedy film called 1st Born where she will play one of the leads.
Melanie Lynskey as Rose – Then
Rose was certainly one of the main actresses on Two and a Half Men. After a one-night stand with Charlie, she became obsessed and started stalking him. For eight years, Rose forms a friendship with Alan and Charlie. Eventually, Rose and Charlie run away to Paris and become engaged. Charlie dies before they have a chance to get married, and Rose is off to her new conquest, Walden Schmidt.
Melanie Lynskey as Rose – Now
Melanie already had quite the acting career even before playing Charlie’s stalker. She has an impressive list of movies and TV shows under her belt like Heavenly Creatures and Sweet Home Alabama. Most recently, however, the 40-year-old actress has been focusing on roles in TV series and is currently in the middle of filming two shows, a mini-series called Sunshine and a Stephen King inspired series called Castle Rock.
Jennifer Taylor as Chelsea Melini – Then
Chelsea Melini was the first woman Charlie every confessed his love to. At first he says it by accident, but then admits that he meant it. Chelsea was supposed to be just another one of Charlie’s one-night stands but it turned into a serious relationship. In order to get Chelsea to say “I love you” back, he proposes to her. Chelsea ends up leaving Charlie for Alan’s attorney and Charlie gets with her best friend, Gali. Safe to say it wasn’t a happy ending for the two.
Jennifer Taylor as Chelsea Melini – Now
After playing the role of Charlie’s love interest on Two and a Half Men, she continued to take parts in several television shows and movies. Most recently she played Anne Seery on the Showtime hit series Shameless. She has also made guest appearances on shows like Mom, with Anna Faris, and NCIS. The now 45-year-old is married to songwriter Paul Taylor and they have two kids, a son and daughter.
Holland Taylor as Evelyn Harper – Then
Evelyn Harper played the role of Charlie and Alan’s ‘loving’ mother. She and her sons and grandson had a pretty superficial relationship and they tried to avoid each other whenever possible. She got married numerous times and had a tendency for marrying rich older men who left her large amounts of money after they passed away.
Holland Taylor as Evelyn Harper – Now
The now 74-year-old isn’t letting her age get her down. She is still acting after her long run with Two and a Half Men. Since playing the Harper brothers’ mom, she has acted in minor roles in TV series such as Hollywood Mom and The Orville. She currently has taken on a larger role and plays Ida Silver in the TV thriller series Mr. Mercedes. She is dating the 42-year-old actress Sarah Paulson who is known for her role in American Horror Story.
Marin Hinkle as Judith Harper-Melnick – Then
Judith Harper-Melnick was Alan’s first wife and mother to his son Jake. The couple divorced after a cold marriage. Alan’s ex-wife enjoyed spending her ex-husband’s alimony money on shopping and plastic surgery. Judith went on to remarry Jake’s pediatrician, Dr. Herb Melnick and Alan was thrilled, as it meant he didn’t have to pay alimony anymore. Eventually, Herb has an affair with his secretary and Judith divorces him.
Marin Hinkle as Judith Harper-Melnick – Now
Marin went on to play Isabelle in the CBS drama Madam Secretary. This year the 51-year-old played Christine Lonas in the show Homeland and Dr. Miller in the series Speechless. She just finished filming for an upcoming drama film titled Before/During/After. Unlike her character on TAAHM, Marin is in a long and happy relationship with her theater director husband, Randall Sommer.
Courtney Thorne-Smith as Lyndsey McElroy – Then
Lyndsey was a major recurring character on the show, and had an on again off again relationship with Alan from season 7 and on. They split up and got back together too many times to remember. Her son Eldridge just happens to be Jake’s best friend. Lyndsey always loved Alan but had a drinking problem and often was attracted to other men, like Walden, while she was with him.
Courtney Thorne-Smith as Lyndsey McElroy – Now
After 5 years of playing Alan’s complicated lover, the 49-year-old has only taken a few acting gigs. She was a voice actress for the Adult Swim animated comedy Robot Chicken, and appeared in two episodes of the abc comedy Fresh Off the Boat. She is currently married to her second husband, Roger Fishman, whom she has a 9-year-old son with named Jacob.
Allison Janney as Beverly – Then
Alan met Beverly on a dating site and told her that Charlie’s house was his in order to impress her. After talking on the porch, Beverly tells Alan about her divorces and Alan opens up and tells her the truth about the house. Beverly didn’t seem to mind Alan’s fib since she has a worse background than him. The two get together and Charlie walks in on a tied up Alan who just says, “everyone makes mistakes.”
Allison Janney as Beverly – Now
Allison has been in too many movies and television shows to even count. The successful actress was known best for her role as C.J. Cregg in The West Wing before her appearance on TAAHM. Since then, she has been in several movies such as Hairspray, Juno and The Girl on the Train. Now 57 years old, Allison is probably most recognized for her current role in the CBS com-dram series Mom, where she plays the alcoholic mom of Christy (Anna Farris.) In 2014 and 2015 the part landed her an Emmy for Outstanding Supporting Actress in a Comedy Series.
Brooke Shields as Danielle Stewart – Then
Danielle was set up on a date with Alan by Charlie by his attempt for him to move out and live with her. Danielle had a somewhat promiscuous past and thought settling with Alan would be a good decision for her. After a night of drinking, Danielle tells Charlie about about her background and Charlie decides he wants to be with her. The brothers fight over her until Danielle finally leaves, slipping on Jake’s skateboard on the way out.
Brooke Shields as Danielle Stewart – Now
The model/actress was definitely a well-heard of name in Hollywood long before her guest appearance on TAAHM. She’s been acting since she was a child and has been in countless TV shows and movies. After her minor role in the show, she went on to appear in several movies like The Other Guys and Furry Vengeance. She also appeared on quite a few episodes of the TV drama Army Wives. At 52, Brooke is still as beautiful as ever and has a recurring role on Law & Order: Special Victims Unit. She now has two children with her screenwriter and producer husband Chris Henchy.
Jeri Ryan as Sherri – Then
Sherri is on Charlie’s long list of girlfriends. He saw her as the female version of himself. The two dated but Charlie got sick of her playing hard to get all the time so they split. As Charlie and Alan are at an eye doctor’s office, they bump into Sherri and Alan starts dating her. Like most relationships on the show, it didn’t last long and they ultimately broke up.
Jeri Ryan as Sherri – Now
The 49-year-old actress has had several TV appearances since TAAHM. Her list of shows include Leverage, Body of Proof, Helix, Major Crimes and currently the Amazon Prime series Bosch. Her most well-acclaimed role was in Star Trek: Voyager as Borg Seven of Nine, which landed her a Saturn Award. In 2007, she married French chef Christophe Eme and the couple now has two children.
Kimberly Williams-Paisley as Gretchen Martin – Then
Gretchen was Larry’s (Lyndsey’s fiancé) sister on the show and started dating Alan, who went by his alter-ego ‘Jeff Strongman’. Alan gets carried away with his new identity and even calls Barry (Walden’s friend) his son and Barry’s apartment, his own. Gretchen opens up to Alan about her ex-husband who lied to her all the time, and eventually Gretchen finds out about Alan’s own lies and leaves him.
Kimberly Williams-Paisley as Gretchen Martin – Now
Like many of her costars, Kimberly already had a long resume before her role in TAAHM. She was known best for her character in the Father of the Bride movies with Steve Martin, and also for her eight-year role in According to Jim (alongside TAAHM costar Courtney Throne-Smith.) The 46-year-old is now post-production for a holiday film called The Christmas Train. She is married to country superstar Brad Paisley and the couple have two children together.
Judy Greer as Bridget Schmidt – Then
Bridget is Walden’s ex-wife, and the reason for his attempt to kill himself in his debut episode. Even though Walden begs, she won’t take him back because of his immature nature. As Walden is with Zoey, Bridget comes back to the beach house and asks for him back. With great difficulty, Walden rejects her offer and asks her to sign the divorce papers. She gets so mad that she drives her car into his house.
Judy Greer as Bridget Schmidt – Now
The 42-year-old actress is still keeping busy nowadays with a variety of acting and non-acting jobs. She actually was the casting director for the 2015 movie Entourage. Most recently, Judy has been voice-acting for a kids animated TV series called StoryBots. She also has been a voice actress for the FX animated comedy Archer since 2009. On top of that, she just accepted a role in the newest remake of the classic horror film, Halloween.
Sophie Winkleman as Zoey Hyde-Tottingham Pierce – Then
Zoey was Walden’s British girlfriend and was the first serious relationship after his divorce with Bridget. Walden and Zoey, a single mom, continue dating from the 9th to 10th season. Walden proposes to Zoey and she sadly rejects. He later finds out that she was seeing someone else, and to get revenge he gives her daughter a destructive dog as a birthday present.
Sophie Winkleman as Zoey Hyde-Tottingham Pierce – Now
The British actress is actually married to royalty, her husband is Lord Frederick Windsor, the son of Queen Elizabeth II’s cousin. Shortly after she finished filming with TAAHM, she got a job as a voice actress for Milo Murphy’s Law. She is currently acting again, and is in the middle of shooting for a new TV crime-drama series called Trust alongside Hilary Swank and Donald Sutherland.
Ming-Na Wen as Linda Harris – Then
Linda met Charlie on a double date that Alan set up. Charlie liked her, but she was disgusted by his rude nature. Later on, Charlie gets pulled over for driving under the influence and ended up in a courtroom with Linda as his judge. Linda thought it was Charlie’s attempt to see her again. She fined him $500 and decided to give him a second chance. The pair date for some time until Charlie embarrasses Linda at an award ceremony in her honor.
Ming-Na Wen as Linda Harris – Now
If Ming-Na’s voice sounds familiar, it is probably because she was the voice of Mulan in the Disney movie. She also had a leading role in the series ER. After having several appearances on TAAHM, Ming-Na went to play roles in multiple TV shows like SGU Stargate Universe and Eureka. Now 53, Ming-Na currently plays Melinda May on the TV sci-fi action series Agents of S.H.I.E.L.D.
Heather Locklear as Laura – Then
Laura was Alan’s divorce lawyer, until Charlie decided to sleep with her. Laura made Charlie promise that he would always be available for her, but when Charlie broke his promise, she got revenge by messing with Alan’s divorce settlement with Judith. The revenge mostly just hurt Alan, and not Charlie, Alan ended up firing her and had to find a new attorney.
Heather Locklear as Laura – Now
Heather was known before her time on TAAHM as Amanda Woodward on the soap opera Melrose Place. Since then, she went on to take roles in TV series such as LAX and Franklin & Bash. She also played a role in Scary Movie 5. The now 56-year-old is currently playing First Lady Katelynn Christian in Tyler Perry’s drama series Too Close to Home.
Gail O’Grady as Mandi – Then
Mandi is Kandi’s mom. Kandi was Alan’s wife at the time, and she came one day to Charlie’s house looking for her daughter. While she was there, she met Charlie. The two end up hitting it off and they spend the entire day together. Her and her daughter look a lot alike, and people often mistake them for sisters.
Gail O’Grady as Mandi – Now
Gail made her appearance on TAAHM after playing the role of Helen Pryor in the TV series American Dreams. She has been in multiple TV shows and films since. Her most recent as Stevie Grayson in the show Revenge and Ms. Fields in the horror film Lycan. The 54-year-old has been married 6 times, but she is now taking a break at the married life. Her most recent marriage to John Stamatakis ended in 2008.
Paula Marshall as Paula – Then
Alan met Paula at a club and the two hit it off right away. After they get to talking, Paula tells Alan that she used to be a man named Paul. Alan doesn’t mind and the couple start dating. Alan later meets Rachel who used to be married to Paula. Paula tells Alan that he can be with anyone he wants while they are together, and Alan chooses to take Rachel on a date at a club. Paula sees the two together and kisses Rachel. They got back together and Alan was left single again.
Paula Marshall as Paula – Now
Since appearing on TAAHM, the actress has played Barbara Wilkerson in the series Murder in the First, and Lora Fuller on Gortimer Gibbon’s Life on Normal Street. She most recently appeared as Diane in the comedy film, We Love You, Sally Carmichael!. The 53-year-old is married to actor Danny Nucci, who is best known as Fabrizio in Titanic. The couple have a 12-year-old daughter together named Maya.
Missi Pyle as Miss Pasternak – Then
Miss Pasternak was Jake’s teacher. Charlie started dating her and she started giving Jake good grades. Charlie dumped her because he found out she was actually mentally ill. A few seasons later, we find out that she lost her teaching license and was now living in a motel and working as an exotic dancer. Charlie asks her to move in with them and even gives her a job as Jake’s tutor. She eventually becomes religious and asks Charlie to marry her, he dumped her instead.
Missi Pyle as Miss Pasternak – Now
Since her role on TAAHM, Missi has been acting here and there in several different TV shows. She has appeared on comedy series Inside Amy Schumer, The Soul Man, Sing It! And Another Period. She also appeared in the films Gone Girl and The Artist. The 44-year-old will be seen next as the role of coach Webb in the upcoming film Jumanji: Welcome to the Jungle.
Kimberly Quinn as Donna – Then
Alan met Donna in the same blind date where Charlie met her friend Linda Harris. The two continue to date until Alan gets bored with the relationship. At first, he didn’t want to break up with her because he didn’t want to hurt her feelings, but Charlie told him exactly what to say and how to break up with her. Alan went to her house to break up, and she started crying hysterically.
Kimberly Quinn as Donna – Now
Since her two-episode role on TAAHM, Kimberly has continued to work as an actress. She played Tess Masterson in the ABC series Twisted and is currently playing Holly in the Netflix thriller show Gypsy. She is currently married to her producer husband Theodore Melfi. He is known for his work in the films Hidden Figures and St. Vincent (where Kimberly played Nurse Ana.)
Tammy Lauren as Shannon – Then
Alan met Shannon at Herb and Judith’s wedding. She told him that she was Herb’s ex-fiance and the two started kissing in the coatroom. Alan wasn’t ready to take it further, but they decided to pretend like they were making love in order to make the new married couple jealous. The two made quite a scene while Shannon yelled Alan’s name in hopes of her ex-fiance.
Tammy Lauren as Shannon – Now
After her episode on TAAHM, the actress continued playing Detective Maggie Sullivan on the soap opera The Young and the Restless. Since then, she appeared in one episode of Criminal Minds in 2014 and that’s about it. At 48, it seems like she is taking a break from her acting career. She is currently married to actor Guri Weinberg, and has been since 1997.
Justine Eyre as Gabrielle – Then
Justine was Charlie’s girlfriend who Alan tried to steal after finding out that Charlie stole his high school girlfriend, Charity, away from him. In a desperate attempt to get revenge on his brother, Alan gets with Gabrielle but decides that it was too “uncomfortable” so he decides to go home. When Alan gets home he finds Charlie with Charity, who tells Alan “now we’re even.”
Justine Eyre as Gabrielle – Now
After Justine’s minor role in TAAHM, she has been only acting here and there. She went on to play an episode of CSI: Miami and The Secret Life of the American Teenager. She also voiced several characters in the video game Uncharted 4: A Thief’s End. The Canadian beauty married actor and screenwriter John Allen Nelson in 2007.
Maggie Lawson as Ms. McMartin – Then
Ms. McMartin was a social worker who was assigned to Alan and Walden after the “couple” decided to adopt a child. She assigns them to a 6-year-old boy named Louis. However, after finding out about their deception she takes Louis from their home. Alan sleeps with her in attempts to make her change her mind. After she sees how comfortable Louis is with Walden and Alan, she decides not to take him away. Ms. McMartin eventually leaves Alan, who is still in love with Lyndsey, and starts dating Walden.
Maggie Lawson as Ms. McMartin – Now
After Maggie’s appearance in the final season of Two and a Half Men, she went on to play Allison in Angel from Hell and Rachel in The Great Indoors. The 37-year-old will be reliving her role as Juliet O’Hara in the upcoming film, Psych: The Movie. In 2015, Maggie married her actor husband Ben Koldyke, who is known for his role in NBC’s Mr. Robinson, in a Las Vegas wedding.
Krista Allen as Olivia Pearson – Then
Olivia was Charlie’s girlfriend before season 1, who ran into Charlie at Evelyn’s house when she invited her and her father (Evelyn’s boyfriend) over for dinner. Once revealed that Charlie and Olivia dated before, and that it didn’t end well, the two began to argue and ruined the dinner. Olivia threw her drink in Charlie’s face and everyone was sent home. Tommy later left Evelyn for a much younger woman.
Krista Allen as Olivia Pearson – Now
Krista has been acting since the early 90s, with her first major role as Billie Reed in the long-running soap opera Days of Our Lives. She also has been in several movies such as Anger Management and The Final Destination. Most recently, she has been keeping busy and just finished acting several projects. The 46-year-old will be seen in the upcoming comedy film titled Best Mom and a sci-fi comedy called Eleven Eleven.
Teri Hatcher as Liz – Then
Liz is Judith’s sister who got together with Charlie in the coatroom at Alan and Judith’s wedding although she doesn’t remember him. She first appeared during Jake’s 11th birthday party where after hitting on Alan, Judith gets angry. The two sisters start fighting and it turns out that Alan asked Liz out before asking Judith. Judith was so upset that she took Charlie to her room and Liz takes Alan. In the end, both sisters back out.
Teri Hatcher as Liz – Now
Shortly after her appearance on TAAHM, Teri went on to the role of her lifetime as Susan Mayer in the long-running series Desperate Housewives. After 8 years on Desperate Housewives, she continued to act in a few TV roles here and their such as Charlotte in The Odd Couple and is currently playing Rhea in the CW show Supergirl. Now, 52, Teri is enjoying the single life after two marriages that both ended in divorce.
Kristin Dattilo as Cindy – Then
Cindy is known as one of the only women that Charlie was not able to sleep with. After Jake meets her, he develops a crush on her and even draws her bottom for his art class project. Cindy later meets Judith and the two form a friendship due to their shared issues with their fathers. Cindy even teaches Judith to surf and the two go to the movies together. They become so close that Alan thinks that they have become lovers.
Kristin Dattilo as Cindy – Now
Before her minor role in TAAHM, Kristin was known for playing Yola Gaylen on The Chris Isaak Show. Later on, she appeared in a few episodes in the comedy series Grounded for Life and also appeared in Dexter as Detective Barbara Gianna. The now 46-year-old’s most recent role was in 2016, where she played Maddie Harmon in the film How to Get Rid of a Body (and still be friends.)
Liz Vassey as Kate McLaughlin and Michelle – Then
Liz is a nice, single mom who Charlie first meets at Jake’s soccer game. She laughed at his appearance because he had been drinking and just escaped from two women who were friends of Judith’s. The two started talking and eventually went on a few dates, where Kate confessed how stressful her life really is. Liz played another role later on in season 8 as Charlie’s dermatologist named Michelle. After she removed a mole from Charlie’s rear end, the two started dating until she broke up with him after suspecting he had feelings for Rose.
Liz Vassey as Kate McLaughlin and Michelle – Now
Liz was so good on TAAHM, that she got not just one, but two roles! Nowadays, the 45-year-old is appearing as Gillian Hunt in the action sci-fi series Riley Parra. Before that, she played Nikki Beaumont in the short-lived drama series Nikki & Nora: The N&N Files. Of course, she is still most well-known for her 5-year performance as Wendy Simms on CSI: Crime Scene Investigation.
Paget Brewster as Jamie Eckleberry – Then
Charlie and Alan knew Jamie from their childhood days, and remembered her being unattractive and overweight and even called her “Eckleberry hound.” When they run into her years later they see that she has since become gorgeous and lost a lot of weight. Charlie and Alan each take turns trying to hit on her, but happily rejects them both after remembering how mean they were to her when they were young.
Paget Brewster as Jamie Eckleberry – Now
Paget has appeared in a large variety of TV series over the years and was once even in a few episodes in Friends (she played Kathy, who dated both Joey and Chandler.) She also played Frankie Dart in the NBC show Community. Her biggest role has been as Emily Prentiss in Criminal Minds, whom she has been playing since 2006. The 48-year-old has also voiced several characters in the animated series American Dad.
Rachel Cannon as Chloe – Then
Chloe was Charlie’s girlfriend who he was always trying to get rid of. When a handsome handyman named Fernando (played by Enrique Iglesias) shows up to Charlie’s house to fix his deck, Chloe falls for him and suddenly Charlie gets jealous and is interested in her again. Trying to appear younger, he goes to Fernando’s house dressed like a “young boy” to get Chloe back right as the two are about to “do it.” Eventually he bribes her back to him with money and fires Fernando.
Rachel Cannon as Chloe – Now
Rachel is a familiar face in the world of television, and has been in many shows such as Ghost Whisperer, The Big Bang Theory, Mad Men and Underemployed. Unfortunately, most of her roles have been on the smaller side, but hopefully she will be a leading lady in the near future! The pretty blonde’s most recent role is Deidre in the successful ABC sitcom Fresh Off the Boat, which she has been a part in for the last two years.
Sara Rue as Naomi – Then
Naomi is Berta’s daughter who is known to her mother as her pride and joy. She is pregnant and jobless when introduced to Charlie and Alan and has no choice but to move in with her mother for support. She develops feelings for Alan and kisses him, but goes into labor shortly after and gives birth to a baby girl named Brittany Pam. After she gives birth, she decides to date Alan secretly until Berta finds out and is surprisingly happy since Alan is the nicest man Naomi ever dated. After Brittany’s biological father Hector returns, Naomi leaves Alan and gets back together with Hector.
Sara Rue as Naomi – Now
Sara is still acting in dozens of TV shows including Mom, Impastor and Bones. Before TAAHM, the actress was known for her role as Carmen Ferrara in the series Popular and Claude Casey in the show Less Than Perfect. She also appeared in a few movies such as The Ring and Pearl Harbor. Now, the 38-year-old is working on her newest role as Librarian in the upcoming Netflix show A Series of Unfortunate Events.
Stephany Jacobsen as Penelope – Then
Shortly after Walden buys recently deceased Charlie’s house, Penelope, a woman wearing a bikini, shows up at the door looking for Charlie. After hearing the news about his death, she is sad but quickly gets over it by seeing Walden. Walden’s ex-wife Bridget shows up at the sane time to talk to Walden, Alan saves the day by pretending to be Penelope’s boyfriend explaining to a suspicious Bridget why she is there.
Stephany Jacobsen as Penelope – Now
Before her quick appearance on TAAHM, Stephany was known for her long-running role as Charlotte Adams on the series Home and Away and Kendra Shaw in the sci-fi film Battlestar Galactica: Razor. She also played Lauren Yung for a year from 2009-2010 on Melrose Place. After appearing in a few episodes on the shows Revenge and Star-Crossed, the actress took a 4-year break from acting. In 2018, the 37-year-old will be seen in the upcoming sci-fi thriller movie, Occupation.
Jaime Pressly as Tammy – Then
Tammy is a 36-year-old woman and mother of three children who dates Jake in the 10th season. She is covered in tattoos and runs her own tattoo shop called Tammy’s Tatties. Alan does not approve of Jake dating someone twice his age and Tammy is surprisingly understanding about the situation. Eventually the two break up after she finds out that Jake hooked up with her daughter, Ashley.
Jaime Pressly as Tammy – Now
Jaime has had an overall successful career in Hollywood. She has been in several films like I Love You, Man, and Not Another Teen Movie. She now seems to be focusing more on TV shows and was seen as Annie Watson in I Hate My Teenage Daughter from 2011-2013. Currently, she is playing Jill Kendall on the hit CBS show Mom starring Anna Faris and Allison Janney.
Miley Cyrus as Missi – Then
Jake met Missi after coming home for a weekend from the Army. He falls for her right away and they quickly form a relationship. When Jake is leaving to go back to base, Missi reveals that she actually has a boyfriend. Later on Jake and Missi plan a romantic evening at the beach house, but it doesn’t end well after Alan is informed that his son went AWOL from the Army. After confessing his love for Missi, she gets uncomfortable and convinces Jake to go back to the army.
Miley Cyrus as Missi – Now
Of course, Miley is not new to television. Although she now is a huge pop star, who just released her sixth studio album Younger Now last month, she rose to fame years ago with her Disney show Hannah Montana. Now 24, the young actress/singer is more successful than ever. She has won several awards and nominations for her music including an MTV Video Music Award in 2014 for Video of the Year.
Megan Fox as Prudence – Then
Prudence is Berta’s 16-year-old granddaughter who appeared in season 1. Berta said that she can’t leave her alone in the house so she is forced to bring her everywhere with her, including Charlie’s beach house. Charlie, Alan and Jake all develop a crush on her. After having a fight with her grandmother later that night, she comes back to the house and tells them that she is planning on running away to Vegas with her boyfriend Freddie to get married. Before she is able to do so, Berta shows and with Prudence’s mother, Cheryl Ann. As Cheryl is preaching to her daughter, she notices Charlie and becomes interested, until Berta grabs both girls and pushes them out the door.
Megan Fox as Prudence – Now
Megan’s career took off shortly after appearing in Two and a Half Men. The gorgeous brunette performed as Sydney Shanowski in the series Hope & Faith, and then landed the role as Mikaela Banes in Transformers the following year. She went on to play in the Transformers sequel, before getting fired from the franchise due to her “diva-like” behavior. Her most recent role was as Reagan in the hit Fox series New Girl (starring Zooey Deschanel.)
Conchata Ferrell as Berta – Then
Probably one of the most comedic and popular roles on the show was Berta. Berta was the cynical but caring housekeeper of Charlie’s beach house. Berta was always the first to make fun of the Harper brothers and was constantly amused at their many faults. After Charlie passes away, Walden hires her to clean his house as well, and she is more than willing to do it.
Conchata Ferrell as Berta – Now
Although to Two and a Half Men fans, she will always be seen as Berta, the actress has moved on to other roles since the show’s finale in 2015. The 74-year-old played Aunt Dorothy in the Christmas fantasy movie called Krampus, and is currently playing Shirley on the Colorado-based comedy series The Ranch. She is married to actor Arnie Anderson and has a daughter named Samantha.
Kelly Stables as Melissa – Then
Melissa is Alan’s former secretary who first dated Charlie. After that relationship ended disastrously, she drove to Alan’s office where he was forced into giving her a raise and health insurance. She started to fall for Alan and the two date until she catches Alan in a lie about renting a house. They continued to get together even after Alan moved in with Lyndsey in season 8, but Alan eventually ends things for good with Melissa via text message.
Kelly Stables as Melissa – Now
Before her 3-season appearance on TAAHM, Kelly was known best for voicing the character Will Vandom in the animated series W.I.T.C.H. Kelly is still landing roles in TV and film. In 2014, she played Rachel in the movie Horrible Bosses 2 and in 2011-2015 she played Eden in the TV Land series The Exes. The now 39-year-old is currently playing the role of Kate Marshall in the new comedy series Malibu Dan the Family Man.
Jenny McCarthy as Courtney Leopold – Then
Courtney was introduced to Charlie as Teddy’s (Evelyn’s fiancé) daughter. The two date despite Alan warning him that she seems like a sociopath. Eventually, Courtney tricks Charlie into buying her a Ferrari and lending her $50,000. After proposing to Courtney, he finds out that her real name is actually Sylvia and that she and Teddy are both con-artists and lovers. Sylvia went to prison and returned to Charlie, who welcomed her with open arms. Eventually she conned him once again, and used Charlie’s money to go shopping until they finally split.
Jenny McCarthy as Courtney Leopold – Now
The ex-playboy bunny was already famous before her appearance on Two and a Half Men. The blonde bombshell even had her own television show in the late 90s. Jenny was most recently seen playing herself in the show about New Kids On The Block’s Joey McIntyre called Return of the Mac. In the show, she stars with her real-life husband, Donnie Wahlberg, who is the founding member of the 80s boy band. Besides acting, she also is an avid activist against vaccinations.
April Bowlby as Kandi – Then
Kandi is the 22-year-old ditzy girl who manages to hook up with Charlie, Alan and her and Alan’s Ex’s divorce lawyer. Kandi and Alan get married in Vegas, and his new wife moves in with him. Eventually Kandi gets an acting gig as a detective on a show called “Stiffs.” She breaks up with Alan for having hair in his ears, nose and on his chest and mostly because he didn’t want to have kids.
April Bowlby as Kandi – Now
Like most of her cast mates, April Bowlby is still acting. Since leaving Two and a Half Men, the now 37-year-old has played mostly minor roles in TV series such as The Big Bang Theory and Mom. However, she is currently in the middle of filming for an upcoming comedy thriller movie called Love me or Else. The actress is currently single but was known for dating the famous singer Josh Groban.