Where Are The Women From Two And A Half Men Today?

Jennifer Taylor as Chelsea Melini | Then

Charlie Sheen plays the notorious character known for his womanizing ways. So imagine the fans’ shock when the first time he ever admits he’s in love was to Chelsea Melini, played by Jennifer Taylor. At first he plays it off as an accident, but admits his feelings eventually. Although this relationship started as most of Charlie’s do – a fling – it went on to be far more serious. She even says she loves him back when he proposes to her! Sadly, she ends up leaving him for Alan’s lawyer.

Jennifer Taylor as Chelsea Melini | Now

Jennifer Taylor continued her acting career post-Two and a Half Men, going on to play characters in films and TV shows like Shameless, NCIS, and Mom alongside Anna Faris. The woman who played Charlie’s first love is currently 45 years old and is married to songwriter Paul Taylor, with whom she has two beautiful children.

Emmanuelle Vaugier as Mia | Then

Emmanuelle Vaugier played Mia, another woman who made a significant impact in Charlie’s life. She is a dance teacher who originally has no interest in Charlie until he claims that Jake, his nephew (the “half” man in Two and a Half Men), likes dancing. She agrees to date him on the condition that he gives up smoking, drinking, and eating meat. In true Charlie fashion, he agrees but continues to do all of that behind her back. She ends up breaking with him, but later returns to ask Charlie to be her sperm donor. The couple even almost make it down the aisle, but she leaves him when Charlie tells her Alan, his brother, won’t be moving out of his beach house!

Emmanuelle Vaugier as Mia | Now

Two and a Half Men was one of the stepping stones of Vaugier’s career. After her stint on the show, she continued acting on TV in shows like Lost Girl, and Mistresses, as well as TV movies like Destruction in Los Angeles, and Washed Away. She is currently 41 years old, and doesn’t seem to be tired of acting just yet; she is filming a movie called Masks Don’t Lie right now.

Holland Taylor as Evelyn Harper | Then

Holland Taylor played Evelyn Harper, the neglectful yet oh-so-funny mother of Charlie and Alan Harper. She was known for marrying wealthy, older men and taking their money when they died. Evelyn rarely made an appearance (thanks to her sons attempting to see her as least often as possible); but when she did, the less than ideal relationship she shared with her sons made for some hilarious TV!

Holland Taylor as Evelyn Harper | Now

Holland Taylor is currently well into her seventies, but she hasn’t run out of steam yet! She continues acting in the big and small screens, most notably in TV shows like The Orville, and Hollywood Mom. She was also cast as Ida Silver, a main character on the show Mr. Mercedes. Taylor is also still going strong in the dating game, currently in a relationship with Sarah Paulson (who is in her fourties).

Marin Hinkle as Judith Harper-Melnick | Then

Judith was one of the most notable female characters on the show, and made appearances throughout the entire run of it. She was Alan’s ex-wife, and the mother of their son, Jake. They had a rocky marriage, which led to a rocky divorce. They were constantly butting heads over everything, including her tendency to use Alan’s alimony checks on luxury purchases and plastic surgeries. Halfway through the series, Judith ends up married to Herb Melnick, Jake’s doctor. Although that too doesn’t last, as Herb is caught cheating on Judith with his secretary.

Marin Hinkle as Judith Harper-Melnick | Now

Marin Hinkle is currently in her 50s and is married to longtime husband Randall Sommer. It’s a relief she doesn’t share dating patterns with her on-screen character! She has also built a strong acting career, appearing on dramatic shows like CBS’s Madam Secretary. She also starred as Dr. Miller in Speechless, and as Christine Lonas on Homeland. She’s even made appearances on the big screen, and has just finished filming a movie called Before/During/After.

Courtney Thorne-Smith as Lyndsey McElroy | Then

Lyndsey McElroy played Alan’s on-again off-again girlfriend, and questionable mother of Eldrige, Jake’s best friend. The couple broke up and got back together countless times since her first appearance in season 7, but it was never meant to be. She was also known to be a heavy drinker and a serial-flirt; having even gone after Walden, Ashton Kutcher’s character!

Courtney Thorne-Smith as Lyndsey McElroy | Now

Following her 5-year stint on the show, Courtney Thorne-Smith cooled off from acting for some time. She is currently 50 years old, and is married to Roger Fishman. She also has a son called Jacob from a previous relationship. Recently, she’s made appearances on Fresh Off the Boat, an ABC comedy and voiced a character in the animated series Robot Chicken.

Allison Janney as Beverly | Then

Alan meets Beverly on a dating website and the two meet in person. Alan brings her back to the beach house and in an attempt to impress her, tells her its his own. Later, she opens about her own life’s harrowed past and Alan tells her the truth about the house. She doesn’t seem bothered by it, given her own past. In the end, it doesn’t end well, and Charlie walks in to find that she’s left Alan all tied up – literally!

Allison Janney as Beverly | Now

Allison Janney has since made quite a name for herself in the Hollywood scene. She has appeared in many films like Juno, Hairspray, and The Girl on the Train, as well as many TV shows, most notably her appearance on The West Wing. She currently stars on CBS’s Mom, playing the mother of Anna Faris. The role has even earned her an Emmy, so we say go Janney!

Brooke Shields as Danielle Stewart | Then

In an attempt to get Alan to move out of his beach house, Charlie schemes to get a woman called Danielle together with Alan. Danielle, who had been with many men in the past, had decided it was time for her to settle down and be in a steady relationship. But in a twist of events, Charlie actually ends up liking her himself and they bond. This leads to the two brothers arguing over who gets to be with her, and Danielle ultimately decides she doesn’t want to be with either of them.

Brooke Shields as Danielle Stewart | Now

Brooke Shields had been acting and modeling since childhood, long before she starred on Two and a Half Men. Since her departure from the show, she’s continued acting in many movies and TV shows. Some of her most memorable performances were in movies like Furry Vengence, The Other Guys, and the TV show Army Wives. Brooke Shields may be in her fifties, but she looks as gorgeous as ever – just ask her husband Chris Henchy or their two kids!

Jeri Ryan as Sherri | Then

Charlie had quite a reputation as a womanizer, but when her met Sherri, it seemed he’d met his match. She shared many similar qualities with Charlie and was constantly playing hard-to-get. This finally led to the demise of their relationship. Sherri then tried to pursue a relationship with Alan, but that didn’t last too long either.

Jeri Ryan as Sherri | Now

Jerry Ryan is a German-born actress, who is currently 49 years old and married to French chef, Christophe Eme. Following her cameo on Two and a Half Men, she went to on to star in many TV shows. Major Crimes, Body of Proof, and Helix are just a few of them. Recently, she also starred in an original series by Amazon Prime called Bosch.

Kimberly Williams-Paisley as Gretchen Martin | Then

Lindsey, Alan’s on-again off-again girlfriend gets married to a man called Larry later on in the show. Larry has a sister called Gretchen, who Alan begins dating. Alan comes up with an alter-ego to impress her, changing his behavior and even claiming his son’s apartment was his own. When Gretchen find out about all the lies he’s been telling her, she breaks it off saying her marriage had failed because her ex-husband constantly lied to her.

Kimberly Williams-Paisley as Gretchen Martin | Now

Kimberly Williams-Paisley, the actress who played Gretchen, was no stranger to the screen when she appeared on Two and a Half Men. She’d starred in the hit-comedy film Father of the Bride, and on a recurring role in According to Jim for 8 years. She gets the latter of her two surnames from husband and country singer Brad Paisley, with whom she has two children. One things for sure, that’s one good looking couple!

April Bowlby as Kandi | Then

April Bowlby portrays a young, ditzy woman called Kandi who ends up dating Charlie, Alan, and Alan’s former lawyer. Eventually, she marries Alan in a Vegas wedding and moves in with him. The marriage didn’t last long, though, as she breaks it off with him when she lands a part in a show called “Stiffs”. She says she’s breaking up with Alan because he has hair on his nose and ears… and oh, because he doesn’t want to have kids with her.

April Bowlby as Kandi | Now

Since her departure from Two and a Half Men, April Bowlby continued acting, and has had small roles in popular TV shows like The Big Bang Theory, How I Met Your Mother, and Drop Dead Diva. Her latest ventures are a movie called Love me or Else and a project called Reunion. April is also popular for having dated famous singer Josh Groban.

Judy Greer as Bridget Schmidt | Then

When Charlie Sheen left the show, there was one man missing from the Two and a Half Man, and this spot was filled by Walden (Ashton Kutcher), a wealthy yet extremely emotionally unstable divorced man. Judy Greer plays Bridget, his ex-wife who he still in in love with. He goes so far as to even try to take his life because she won’t take him back, but Bridget refuses, stating he is too immature. This changes when she finds out he is dating a girl named Zoey and she begs him to take her back, but instead he offers to finalize their divorce.

Judy Greer as Bridget Schmidt | Now

Judy Greer has an impressive list of credits, and not just to acting. She went behind the scenes as a casting director in a movie adaptation of Entourage and has voiced several animated characters, including in the shows StoryBots and Archer. She has appeared in many TV shows and movies, including Arrested Development, How I Met Your Mother, Modern Family, 27 Dresses, Carrie, Jurassic World, and so much more.

Sophie Winkleman as Zoey Hyde-Tottingham-Pierce | Then

Zoey was an attractive British woman who became Walden’s first and serious girlfriend after his divorce from Bridget. She was a single mother, and the couple dated for two seasons. But when Walden proposes, she turns him down. In the end, Walden finds out she’d been dating another man behind his back. In an attempt to get back at her, he gifts Zoey’s daughter a vicious dog for her birthday.

Sophie Winkleman as Zoey Hyde-Tottingham-Pierce | Now

Sophie Winklemen is actual real-life royalty, albeit by marriage, as she is married to Lord Frederick Windsor, who is a distant cousin of Queen Elizabeth. After she left Two and a Half Men, she voiced a character on the show Milo Murphy’s Law. More recently, she’s back in front of the camera on a show called Trust, alongside Donald Sutherland and Hilary Swank.

Melanie Lynskey as Rose | Then

Of all the women who came and went on the show, Rose is one of the most memorable. This very unstable women grows obsessed with Charlie after a one-night stand and ends up stalking him. Although Charlie deflects her attempts to get with him in the beginning, he actually gets engaged to her and runs off to Paris with her later on in the show,. But in the end, Charlie dies before they can get married.

Melanie Lynskey as Rose | Now

Melanie Lynskey hails from New Zealand, and was married to Jimmi Simpson until their divorce in 2014. She is also a pretty familiar face on screen, having appeared in movies like Sweet Home Alabama and Heavenly Creatures, among others. Currently, she is working on two new shows called Castle Rock, as well as Sunshine and Stephen King.

Ming-Na Wen as Linda Harris | Then

It is actually Alan that sets Charlie up with Linda in a double date. Charlie is captivated by Linda, but she is put off by his rude and ill-mannered personality. Little does Charlie know he’ll end up facing her as a judge when he gets charged with a DUI! Ultimately, Linda decides to give Charlie second chance, but breaks up with him when he embarrasses her during a ceremony where she was receiving an award.

Ming-Na Wen as Linda Harris | Now

Ming-Na Wen had done quite well for herself since her stint on the show, going on to star in many other shows like ER, Eureka, and SGU Stargate Universe. She was also the voice behind Disney’s Mulan. She currently stars in a sci-fi series called Agents of S.H.I.E.L.D. Ming-Na Wen is married to Eric Michael Zee, and has two children with him.

Heather Locklear as Laura | Then

Heather Locklear played Laura, Alan’s divorce lawyer during his split from Judith. But it all went south when Charlie sleeps with her, promises to be there for her whenever she needs him, and breaks his promise in true Charlie fashion. She ends up taking revenge on Charlie by ruining the divorce settlement between Alan and Judith. Alan ends up firing her and getting a new lawyer.

Heather Locklear as Laura | Now

Heather Locklear was no new kid on the block, even before she starred in Two and a Half Men. She had appeared in popular shows like Melrose Place, and Spin City. Unfortunately, Heather went through a harrowing divorce and has faced issue with her health, being in the public eye only making all of it worse. Thankfully, she seems to have bounced back. Recently she’s starred in shows like Franklin & Bash, as well as Tyler Perry’s Too Close to Home.

Gail O’Grady as Mandi | Then

Remember Kandi, Alan’s short-time wife who broke up with him because of nose hair? Gail O’Grady plays Kandi’s mother, Mandi. The two women look eerily similar and often are confused as sisters, rather than mother and daughter. Mandi finds her way to Charlie’s beach house when she comes looking for her daughter, but ends up meeting Charlie and spends the day with him.

Gail O’Grady as Mandi | Now

Gail O’Grady had starred in the TV show American Dreams before her role on Two and a Half Men. Afterward, she continued acting in other projects like Ms. Fields, and Revenge. Her professional life is quite stable, but the same can’t exactly be said about the personal side of things. Gail has been married at least 6 times, her last attempt at marriage ending in 2008. She is currently dating Chris Beyers, and we hope that this time it lasts!

Paula Marshall as Paula | Then

Paula and Alan’s love story isn’t exactly the conventional kind. They meet in a nightclub and hit it off right away. Then Paula reveals that she used to be a man called Paul, which doesn’t Bother Alan. The two start dating, only to be spearheaded by Paula’s ex-wife, Rachel. Paula tells Alan that she wants to be in an open relationship, so Alan begins dating Rachel as well. But when Paula sees Alan kissing Rachel, she realizes her true feelings and the two decide to give their relationship another try, leaving Alan all alone.

Paula Marshall as Paula | Now

Paula Marshall is married to Danny Nucci, who you may know as the character Fabrizio from the movie Titanic. The couple have a daughter called Maya. Paula has continued acting since Two and a Half Men, including many popular TV shows like The Mentalist, Murder in the First, and Switched at Birth. She most recently appeared on the big screen in the movie called We Love You, Sally Carmichael!

Missi Pyle as Miss Pasternak | Then

Charlie set his sights on just about every attractive woman he ever met, and Jake’s elementary school teacher was no exception. Charlie starts dating Miss Pasternak, and as a result Jake starts getting special treatment. But then Charlie finds out she is mentally ill and dumps her. A couple seasons down the line, we revisit Miss Pasternak, only she is now a dancer who lives in a motel. Charlie offers her the job of Jake’s tutor, and she finds religion. She even ends up proposing to Charlie, but he breaks up with her.

Missi Pyle as Miss Pasternak | Now

Texas-born blonde Missi Pyle has appeared in several TV shows after her role on Two and a Half Men, including Inside Amy Schumer, and Sing It. She has also starred on the big screen in famous movies like Gone Girl, The Artist, and the newest Jumanji movie. She continues to work and doesn’t seem to have any idea of slowing down any time soon. Missi Pyle has been divorced twice, and seems to be taking a much deserved break from relationships right now.

Kimberly Quinn as Donna | Then

When Alan sets Charlie up with Linda the judge on their double date, he brings Donna as his own companion for the evening. They start dating, and things seem to be going well until Alan decides to end it because he becomes bored of her. Alan doesn’t want to hurt Donna’s feelings and is unsure of how to tell her, and Charlie gives him advice on how to break in off gently. But the advice backfires and Donna becomes hysterical when Alan breaks up with her.

Kimberly Quinn as Donna | Now

Kimberly Quinn continued her acting career post-Two and a Half Men, starring in TV shows like Twisted, and the Netflix original series Gypsy. She is married to Theodre Melfi, a Hollywood producer best known for his work on movies such as St. Vincent, and Hidden Figures. He even cast his wife in the role of Nurse Ana on St. Vincent.

Tammy Lauren as Shannon | Then

Alan and Shannon meet at his ex-wife Judith’s wedding to Herb. Alan finds out Shannon was actually previously engaged to Herb, and the two hit it off due to their common situations. They get physical in the coatroom at the wedding, and even make quite a scene yelling each others names loud enough for the guests to hear, pretending to be intimate, in an attempt to make their former partners jealous. Ultimately, though, the relationship ends up failing.

Tammy Lauren as Shannon | Now

Tammy Lauren was a series regular on the famous show The Young and The Restless. She played the character Detective Maggie Sullivan, and continued her role even after her guest appearance on Two and a Half men. She seemed to have taken a break from acting since the end of the soap opera, having only appeared in single episodes of the shows Madison Avery, and Criminal Minds. Tammy Lauren in married to actor Guri Weinberg.

Justine Eyre as Gabrielle | Then

Gabrielle is Alan’s high school girlfriend that ends up dating Charlie. When Alan finds out, he accuses Charlie of stealing his girlfriend and plans on stealing her back. Alan’s plan surprisingly works, but he breaks it off with Gabrielle saying their relationship feels “uncomfortable”. Afterward, he goes home to find Charlie with his high school girlfriend, Charity. Alan tells Charlie that they’re now even.

Justine Eyre as Gabrielle | Now

Justine Eyre is a Canadian actress, who is married to screenwriter John Allen Nelson. Although she hasn’t had many roles since Two and a Half Men, she has made guest appearances on shows such as Mad Men, CSI, and The Secret Life of the American Teenager. Her acting career seems to have taken a pause since 2016, but maybe we’ll see her back on the screen soon!

Maggie Lawson as Ms. McMartin | Then

Alan and Walden decide they want to adopt a child, and pose as a gay couple to do so. Ms. McMartin, played by Maggie Lawson, is assigned as their social worker. They are given a baby boy named Louis, but soon after, McMartin finds out that they lied about their relationship. When she goes over to take Louis back, she sees how close he’s grown to the guys and decides to let him stay. Eventually Ms. McMartin ends up dating Alan, only to break it off with him and start a relationship with Walden.

Maggie Lawson as Ms. McMartin | Now

Maggie Lawson has seen great success professionally and personally since starring on the show. Not only is she married to Ben Koldyke, who is also an actor best known for his role in the NBC series Mr. Robinson, she has also starred in many shows herself. Her most notable characters being on shows like Psych, Angel from Hell, The Great Indoors, and even the movie version of Psych which was released at the end of 2017.

Kelly Stables as Melissa | Then

Melissa started out on the show as Alan’s secretary. She begins dating Charlie, but ends up breaking up with him. She then forces Alan to give her a salary bump, as well as health insurance. Afterward, she begins a relationship with Alan. Later she ends up giving him the boot as well when she finds out he’d been lying about renting a house. But the two continue to see each other on and off, once even when Alan was living with Lyndsey. It’s Alan that make the final decision to end it, breaking it off with Melissa for good over a text.

Kelly Stables as Melissa | Now

39-year old Kelly Stables is currently married to Kurt Patino since 2005, and is the mother to their son. She continued acting following her final departure from Two and a Half Men, having starred in movies like Horrible Bosses 2, and TV shows such as Malibu Dan the Family Man, and Superstore. She also voiced a character in the animated show W.I.T.C.H.

Denise Richards as Lisa | Then

Before Alan moves in to his brother’s beach house, Charlie lived there with his girlfriend Lisa. But their relationship ends because of Charlie’s fear of commitment. Later, Lisa tells Charlie that she’s planning to get married to someone else. Charlie tries convincing her to take him back by pretending he’d settled down and become a family-oriented man. Lisa gets married, but ends up divorced later down the line. She gets back together with Charlie, but their relationship ends once again because of the same reason it did the first time: Charlie’s commitment issues.

Denise Richards as Lisa | Now

Denise Richards might have played Charlie Sheen’s girlfriend on the small screen, but she was his actual real life wife at that time! The couple first met in 1991 on Sheen’s movie set, but only got engaged ten years later. They got married in 2001, and became parents to daughter Sam (2004) and Lola (2005). Richards filed for divorce when she was pregnant with their second daughter, and the split was finalized shortly after she was born. Although they have had their troubles, they are good friends today. Richards also adopted another daughter, Eloise, in 2011. The 46-year old continues working as an actress to this day; her resume includes shows and movies like Jane the Virgin, Twisted, Madea’s Witness Protection, etc.

Conchata Ferrell as Berta | Then

Berta was one of the most memorable characters on the show, and probably the only female neither Charlie or Alan tried to get with. She was Charlie’s maid, and was notorious for giving the boys a good dose of reality. She provided a lot of good laughs as she pointed out the brothers’ flaws and made fun of them. She seemed to have no filter, and this was why fans loved her. When Walden moves into the beach house, she accepts his offer to be his housekeeper happily.

Conchata Ferrell as Berta | Now

While Berta remains to be her most popular portrayal, Conchata Ferrell has moved onto other projects since the end of the show. She is currently 74 years old, and doesn’t show any signs of slowing down. She has appeared in films like Krampus, and Deported. She plays a character called Shirley on the comedy show The Ranch. Conchata has one daughter with husband Arnie Anderson.

Jenny McCarthy as Courtney Leopold | Then

When the boy’s mother gets engaged, Charlie meets her fiance’s daughter, Courtney, who he becomes immediately enamored with. They begin dating, but Alan warns Charlie that Courtney displays sociopathic characteristics. Charlie ignores hum, but it becomes apparent Alan is right when she Courtney convinces him to give her $50,000 and a Ferrari. Charlie even proposes to her, but before they can get married, he finds out that her real name is Sylvia and that she and her “father” are actually con-artists.

Jenny McCarthy as Courtney Leopold | Now

Jenny McCarthy was no newbie to the spotlight, having been a Playboy bunny and the star of her own TV show in 1990, before she came on Two and a Half Men. She was also popular for having dated famous actor Jim Carrey. However, the couple split not too long after. Jenny McCarthy is the mother of an autistic boy, and is passionate about raising awareness about the condition. She has also expressed her dislike of vaccinated children publicly.

Teri Hatcher as Liz | Then

Judith’s, Alan’s ex-wife, sister turns up at Jake’s birthday party. It is revealed that Alan had actually asked Liz out first before asking Judith. Liz hits on Alan at the party, which makes Judith mad. In a surprising twist, we also find out that Charlie and Liz had actually got together at Alan and Judith’s wedding, but Charlie does not remember that. In the end, Liz takes Alan to a room, and Judith takes Charlie, although nothing ends up happening with either of them.

Teri Hatcher as Liz | Now

Teri Hatcher struck gold after her appearance on the show. She landed a role on the popular show Desperate Housewives, which put her on the small screen for eight straight years. After the end of Housewives, she’s appeared in a couple shows like Supergirl, and The Odd Couple. Her latest project is a movie called Madness in the Method. Teri Hatcher has been married and divorced twice, and is currently single.

Jaime Pressly as Tammy | Then

During the tenth season of the show, Jake meets and start dating Tammy, an older woman who is the mother of 3 children. She also appears to be quite wild, with tattoos all over her body. Tammy even owns her own tattoo parlor called Tammy’s Titties. Alan isn’t happy about the two dating, given Tammy is twice Jake’s age. Finally, Tammy breaks it off with Jake because she finds out that he had been romantically involved with her own daughter, Ashley.

Jaime Pressly as Tammy | Now

Jaime Pressly is the mother of 3 children in real life as well, and is divorced from their father Simran Singh since 2011. She has appeared on screen several times since her stint on Two and a Half Men. She’s acted in films like Not Another Teen Movie, and I Love You, Man. Currently, you can catch her on the small screen in shows like I Hate My Teenage Daughter, and CBS comedy Mom, alongside another woman who appeared on Two and a Half Men, Allison Janney.

Krista Allen as Olivia Pearson | Then

Charlie visits his mother’s house when she just so happens to have her boyfriend and his daughter, Olivia, over. It turns out that Olivia was a past girlfriend of Charlie’s, before the show’s start. When they meet again and their parents find out about their past relationship, they end up arguing and she throws her drink in his face. Later on, Evelyn’s boyfriend ends up leaving her for a younger woman.

Krista Allen as Olivia Pearson | Now

Krista Allen had been acting long before she came on the show. She got her big break starring on the soap Days of our Lives in 1990. The show has been running for 53 seasons! She also appeared in several movies, like The Final Destination, and Anger Management. Her latest projects include two movies called Best Mom, and Eleven Eleven.

Kristin Dattilo as Cindy | Then

Cindy is someone that stands out, out of all the women that came and went from the show, simply because Charlie could not get her into his bed no matter how hard he tried! Jake ends up enamored by her, and even draws quite a lewd picture of her for a school art project. Judith meets Cindy, and the two end up bonding over their respective deadbeat fathers. They become friends and start doing everything together, which makes Alan suspect that they’re dating.

Kristin Dattilo as Cindy | Now

Two and a Half Men was one of the first projects of Kristin Dattilo’s career. After the show, she went to to star in other television shows, including Dexter and Southland. She then took a break from acting when she became a mother, but later returned to show biz through writing. Along with her many writing projects, she also came back to the screen in a 2016 comedy movie. Kristin Dattilo married Jason Keller in 2005, and the couple have two children together.

Liz Vassey as Kate McLaughlin | Then

Charlie meets Kate at one of Jake’s soccer games. He learns that she’s a single mother, and she laughs at him for drinking at a children’s soccer game. But the two start talking, and Charlie convinces her to go out with him. Liz Vassey appears again later down the show, this time as Michelle, Charlie’s dermatologist. He goes to her about a mole on his back, which she ends up removing. The two start dating afterward, but Michelle breaks up with Charlie, suspecting that he might be in love with another woman.

Liz Vassey as Kate McLaughlin | Now

Liz Vassey appeared in two entirely different roles on Two and a Half Men! After her appearances on the show, she went on to star in a couple other TV shows, including Nikki & Nora: The N&N Files, and Riley Parra. But her most notable role is as Wendy Simms on CSI, where she stayed on for five years. Liz Vassey married David Emmerichs in 2004, and the couple is still together.

Paget Brewster as Jamie Eckleberry | Then

Jamie is a childhood acquaintance of Alan and Charlie, who they used to be quite mean to. She used to be chubby and unattractive, and they would call her “Eckleberry hound”. When Jamie appears on the show, she’s obviously grown p to be a gorgeous woman. This leads to both brothers hitting on her. After leading them on, Jamie gets the last laugh as she rejects them both, reminding them of how terribly they used to treat her when she was little.

Pagent Brewster as Jamie Eckleberry | Now

Paget Brewster has had quite a lot of success since her stretch on the show. She’s acted in many TV shows over the years, including Friends, where she dated both Joey and Chandler. She also starred in shows like Community, Another Period, Grandfathered, and voiced characters on American Dad. But her most notable role was on the CBS crime drama Criminal Minds. She stayed on for 6 years before leaving, but has returned to the latest seasons of the show running currently. Paget Brewster has also starred in a horror film called The Witch Files.

Rachel Cannon as Chloe | Then

Charlie and Chloe dated, but he was never too interested in her during their relationship. In fact, he spent most of his time trying to get away from her. That is, until a handyman that comes to Charlie’s beach house for repairs catches Chloe’s attention. They start dating and Charlie gets jealous. He shows up at the handyman’s house dressed all “hip” in a sorry attempt to impress Chloe, and even offers to bribe the guy. In the end, he ends up firing the handyman and leaves empty-handed.

Rachel Cannon as Chloe | Now

Since Two and a Half Men, Rachel Cannon has appeared in many small roles on several TV shows, such as Mad Men, The Big Bang Theory, Ghost Whisperer, Underemployed, and more. More recently, she’s got a bigger role on the ABC Comedy show Fresh Off the Boat. Maybe you’ll see her in a lead role in a movie or TV show soon enough, who knows!

Sara Rue as Naomi | Then

Naomi is Berta’s pregnant daughter, who has had to move in with her for financial and emotional support. She is also unemployed and going through a tough time. Naomi is attracted to Alan, and the two share a romantic moment right before she fives birth to her daughter, Brittany Pam. Alan and Naomi continue seeing each other, but hide the fact from Berta. Berta eventually finds out about their relationship, but to the surprise of everyone, gives them their blessing saying Alan is the best guy Naomi’s ever been with. In the end, Naomi breaks up with Alan when the father of her child comes back.

Sara Rue as Naomi | Now

Sara Rue was already well into her acting career when she appeared on Two and a Half Men, so she was no stranger to the camera. She had starred in popular shows like Less Than Perfect, The Division, Will & Grace, Popular, and more. Afterward, she appeared in more popular shows like Rules of Engagement, Eastwick, and The Big Bang Theory. Her most recent projects include shows like Bones, and the Netflix version of A Series of Unfortunate Events.

Stephany Jacobsen as Penelope | Then

When Charlie dies and Walden moves into the beach house, a woman named Penelope shows up at the house asking for Charlie. Walden tells her about Charlie’s untimely demise and even though she’s sad to hear the news, she gets over it pretty quickly, having set her sights on Walden. Shortly after, Walden’s ex-wife, Bridget, comes to the house, which leads to Alan claiming Penelope is his girlfriend, so as to not make her suspicious (as at this point, Walden is still pining after Bridget).

Stephany Jacobsen as Penelope | Now

Hong Kong-born Stephany Jacobsen has been acting since the early 2000s. She had already starred in shows like Pizza, Home and Away, and Headland before she came on Two and a Half Men. She also had a recurring role on the remake of the show Melrose Place. Since 2014, Stephany Jacobson has been taking a break from acting. Her final project before hiatus was Star-Crossed, but more recently she has returned to the screen in a film called Occupation.

Miley Cyrus as Missi | Then

When Jake comes home for the weekend on leave from the Army, he meets Missi, a bubbly and sexy woman who he becomes immediately infatuated with. When Jake is getting ready to go back, Missi tells him she already has a boyfriend. The two decide to have a romantic night together, but things go haywire when Alan finds out Jake’s gone missing. Jake ends up telling Missi he’s in love with her, But Missi is uncomfortable as she isn’t able to reciprocate his feelings, and tells him to go back to base.

Miley Cyrus as Missi | Now

As probably one of the biggest stars to ever appear on Two and a Half Men, Miley Cyrus was a very well-received guest star. She was already a superstar, known for her roles in Hannah Montana and her singing career. Her career has been advancing steadily, and she’s received many awards for her songs. The singer is currently 26 years old, and has released her latest album called Younger Now.

Megan Fox as Prudence | Then

Prudence is Berta’s gorgeous granddaughter, who shows up at the beach house because, as Berta tells Charlie, she cannot leave her alone and has to drag her along everywhere. All two and half men (including tiny Jake) are smitten with her, but Prudence tells them she plans on eloping to Las Vegas with her boyfriend, Freddie. When Berta finds out, they get into a huge fight. Ultimately, Prudence plans fails when her mother Cheryl Ann shows up, but she notices Charlie as they are leaving.

Megan Fox as Prudence | Now

Megan Fox is probably more famous than Miley Cyrus, but given that she appeared on Two and a Half Men in season one, her stardom was still in its infantry. It was after her role on the show when she was cast in the show Hope & Faith, as well as the Transformers movie. She starred in following Transformers movie as well, but was fired due to her alleged diva behavior. Most recently Megan Fox appeared on the popular comedy series New Girl, starring Zooey Deschanel.

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