The Ladies Of Two And A Half Men – Then And Now

Published on 07/23/2020

This show is an American television comedy sitcom that was initially aired on CBS for twelve seasons from Sept 2003 to February 2015. Although the title is Two and a Half Men, the show has been graced by many lovely women over the years. This is a comedy sitcom about men, women, dating, divorce, single parenthood, money, and friendship. This TV show will forever be one of the most popular and hilarious sitcoms to grace our screens. Read on to see how the ladies who brought our favorite female characters to life are now doing!

Missi Pyle As Miss Pasternak Then

Miss Pasternak was a teacher that suspended Jake for giving her the finger. That when Charlie started dating her, and it really had a good result. Jake started to get good grades without properly earning them. However, things took a turn for the worse when the teacher revealed that she got banned from her old profession. Charlie ended up dumping her upon the realization that she was mentally ill. And this made her start dancing to pay the bills! This was a short background between Miss Pasternak and Charlie.

Missi Pyle As Miss Pasternak Then

Missi Pyle As Miss Pasternak Then

Missi Pyle As Miss Pasternak Now

Missi Pyle has enjoyed a great acting career in her entire life. She has been on several famous TV shows such as My Name is Earl, Two Broke Girls, Mad About You, Another Period, Bordertown The Soul Man both in 2016, Impulse in 2018, Dirty John in 2020, Friends, and Mom in 2017. Aside from acting that she loves most, she is also passionate about music. In fact, she is part of a country-rock duo called Smith & Pyle! She has been married and divorced twice over the years.

Missi Pyle As Miss Pasternak Now

Missi Pyle As Miss Pasternak Now

Marin Hinkle As Judith Harper-Melnick Then

Marin Hinkle was Alan’s ex-wife since she was cast to play the role of Judy. They really had a weird relationship and tried their very best to co-parent Jake. And this is the reason why they often got into arguments about alimony and child support. Alan often called her out for spending the money on luxury goods and cosmetic surgery. Things got more complicated when Judith fell in love with Jake’s doctor, and this marriage led to a divorce after she found out that he was cheating on her.

Marin Hinkle As Judith Harper Melnick Then

Marin Hinkle As Judith Harper-Melnick Then

Marin Hinkle As Judith Harper-Melnick Now

After Two and a Half Men wrapped up, Marin Hinkle was able to land many acting projects. To name a few, she appeared in another series, which includes Castle; she also joined the cast of Madam Secretary, which she had a recurring role in. On top of that, she also appeared in Speechless and Homeland. When it comes to the big screen, she also worked on the movies with her recent film projects as Before/During/After. She is happily married to Randall Sommer, and they have a child together.

Marin Hinkle As Judith Harper Melnick Now

Marin Hinkle As Judith Harper-Melnick Now

Emmanuelle Vaugier As Mia Then

When the moment Charlie has his eyes on a woman, he will not stop until he has conquered his mission. This is what had happened after meeting a dance teacher named Mia. What he did was, he made Jake dance in order to get closer to her. He agreed to her conditions, such as giving up smoking, drinking, and even eating meat so that he can go out with her. Although Charlie obliged her request, he did it behind her back the reason why she left him in the end.

Emmanuelle Vaugier As Mia Then

Emmanuelle Vaugier As Mia Then

Emmanuelle Vaugier As Mia Now

Vaugier’s career took off when she was done with her stint on the show. The gist is that she has appeared in a remarkable number of TV series. She got to appear on TV shows like Mistresses, Lost Girl, and One Tree Hill. She also snagged a spot on the “Hot 100 List” by Maxim. She also worked on some movies such as Washed Away and in 2016 Destruction Los Angeles. She recently worked on a thriller called Masks Don’t Lie, which was set and shot in Venice, Italy.

Emmanuelle Vaugier As Mia Now

Emmanuelle Vaugier As Mia Now

Holland Taylor As Evelyn Harper Then

Evelyn Harper was a woman who is a regular part of both Alan and Charlie’s life. We are speaking about their mother who was portrayed by Holland Taylor., They had a very complicated relationship with her, but she was then the only female character who could give the guys a piece of her mind. Although she has a reputation for dating older men and being a gold-digger, the viewers very much loved her. But Charlie and Alan are not quite as fond of her as the fans were.

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Holland Taylor As Evelyn Harper Now

The incredible Holland Taylor is a very recognizable face in the entertainment industry. She has been very famous ever since the ‘80s. She received prestigious awards, such as four Best Supporting Actress nominations for her outstanding performance in Two and a Half Men. If you have seen the comedy film Legally Blonde (2001), you will never forget her. The old star nabbed a 2013 Tony Award nomination for her solo Broadway play” Ann.” She is now in a relationship with someone and is happily going on with her acting career.

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Melanie Lynskey As Rose Then

How can we forget about Rose, she portrayed Charlie Harper’s weird neighbor and stalker. Which made the film more so exciting. She refuses to take no for an answer and keeps on stalking him. It was a good thing that things eventually turned around. The result is she ends up with an obsession after spending the night with Charlie. In the end, Charlie agrees to marry her before they run off to Paris. Sadly, this was simply too good to be true. He dies before they can get married.

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Melanie Lynskey As Rose Now

This brunette bombshell has worked on films such as Coyote Ugly, Heavenly Creatures, and Sweet Home, Alabama. It was not until that she bagged leading roles in projects like Hello I Must Be Going, Happy Christma, I Don’t Feel At Home In This World Anymore, and The Intervention. After her appearance in two and a Half Men in 2015, she also appeared in numerous television shows like Key and Peele, Girlboss, and Sunshine. From 2007 to 2014, she was married to Jimmi Simpson. She is currently engaged to actor Jason Ritter.

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Jennifer Taylor As Chelsea Melini Then

Anyone who has watched the show would probably remember Chelsea Melini.Charlie’s first-ever flame. After all, she is the first woman whom Charlie ever confessed his love to. It was said by accident at first, but then he admits that he meant it. He intended for her to remain a one-night stand, but it ends up getting attached, and it turns out in a serious relationship. But then she ends up getting tired of him. Sadly, she leaves Charlie for Allan’s attorney. That’s how the story goes.

Jennifer Taylor As Chelsea Melini Then

Jennifer Taylor As Chelsea Melini Then

Jennifer Taylor As Chelsea Melini Now

She was not supposed to steal the heart of Charlie when the writers first wrote the character. However, that makes more frequent appearances to her after doing so. Then after leaving the said show, Taylor has continued with her career landing several parts in TV shows and film. She has appeared in shows like Mom, recently in the popular Showtime series Shameless where she portrayed as Anne Seery and NCIS in the past. She is happily married to the songwriter Paul Taylor, and they have two kids together.

Jennifer Taylor As Chelsea Melini Now

Jennifer Taylor As Chelsea Melini Now

Allison Janney As Beverly Then

Allan met Beverly on a dating site. He lied to her, claiming that he owns the house. He did everything because he really wants to impress her. Until finally, Beverly admits that she had an issue with her divorce, Allan confessed that it is Charlie’s. The one who kept him when he was in the middle of his divorce. She decided to go along because she said that her problems are worse than Allan. They stay together until Charlie walks in on them and sees Beverly tying Alan up!

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Allison Janney As Beverly Now

Allison Janney is an award-winning actress who has a solid reputation, and she has earned a high reputation in the movie industry. Even before joining the cast of the show, this actress already made a name for herself in the Hollywood industry. She starred in The West Wing from 1999 to 2006 before finally transitioning to feature films. She appeared in Hairspray, Juno, and The Girl on the Train. During these days, she is busy playing the mother role of Anna Faris on a CBS sitcom called Mom.

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Jeri Ryan As Sherri Then

Charlie thinks that he found his match when she met Sherri. She appeared in the “Bad News From the Clinic” episode playing as Charlie’s girlfriend. She does not fall for the usual tricks that he usually pulls on women. Charlie really finds it hard about her attitude to be attractive in the beginning. But then, he eventually tries to see how she is always a step ahead of him. They eventually break it off, although she tries her luck with his brother first. But her plan didn’t work at all.

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Jeri Ryan As Sherri Now

The lovely Jeri Ryan got her big break by playing the Seven of Nine in Star Trek: Voyager. She guest-starred on the series Leverage as Tara Nicole in 2009. Aside from this, she was also in Body of Proof as Dr. Kate Murphy, Special Victims Unit, and Major Crimes. She was married to politician Jack Ryan, but they eventually split up due to their conflicting schedules. The actress is now fulfilling married to Christophe Eme, the father of her two kids.Wishing them more happy years together.

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Kimberly Williams-Paisley As Gretchen Martin Then

Alan starts dating Gretchen Martin, Larry’s sister in Season 11, who also refuses to tell her about the truth. The fact that he is telling her is that the apartment is owned by him and saying that he does not live with his brother. The lies pile up until it is too much for him to keep track of what was started. Until finally, she learns about the deception done to her; she dumps him and says that she used to be married to a pathological liar.

Kimberly Williams Paisley As Gretchen Martin Then

Kimberly Williams-Paisley As Gretchen Martin Then

Kimberly Williams-Paisley As Gretchen Martin Now

The radiant Kimberly Williams-Paisley has been acting since her early age. Among her notable works would be Father of the Bride. On top of that, she also spent eight years on According to Jim. Recently, she worked on movies called The Christmas Train and Darrow and Darrow. In 2003, the actress tied the knot with a country musician by the name of Brad Paisley and renewed her vows last 2015. They have a happy relationship because Brad said that they have a healthy sense of humor.

 

Kimberly Williams Paisley As Gretchen Martin Now

Kimberly Williams-Paisley As Gretchen Martin Now

Ming-Na Wen As Linda Harris Then

Alan plans a double date, on how Charlie meets Linda. He is immediately attracted to her, but she can see right through him and the reason why she turns him down. She keeps on rejecting him. The situation changes when Charlie gets caught by the police drunk and driving. To his surprise, she is the judge of his case. Then she gives him a shot, their little romance does not go on for a long time. Until Linda was invited to an Awarding Ceremony, she got embarrassed because of him.

Ming Na Wen As Linda Harris Then

Ming-Na Wen As Linda Harris Then

Ming-Na Wen As Linda Harris Now

Ming Na Wen is best known for her starring role as Fa Mulan in the animated musical action film Mulan. Merely because she is a non Hollywood star, she was not used to appearing in front of the camera. She was the voice of Mulan in the eponymous Disney movies. Aside from that, she also lent her voice in some animated films like Sofia the First and Ralph Breaks the Internet: Wreck-it Ralph 2. When it comes to TV appearances, she was also in SGU Stargate Universe and Eureka.

Ming Na Wen As Linda Harris Now

Ming-Na Wen As Linda Harris Now

Gail O’Grady As Mandi Then

Charlie goes without saying that he loves ladies and finds it hard to turn them down whoever comes across. This is the reason why he pursued Mandi, who has been searching for her daughter Kandi at Charlie’s house. It all ends up that Mandi spent her whole day with Charlie. Considering the fact that Kandi and Mandi look less like mom and daughter and more like sisters, as we can see it. Alan is not happy to hear that his brother is cozying up to his mother-in-law.

Gail O’Grady As Mandi Then

Gail O’Grady As Mandi Then

Gail O’Grady As Mandi Now

Aside from appearing on Two and a Half Men, Grady has also been in American Dreams, Ms. Fields, and Revenge. Portraying almost the same similar character on the show. The actress has gotten married six times in the past. She broke up with artist Robert Claypool in 1995.Her last relationship was with John Stamatakis ended in 2008. She has a child with his former boyfriend Chris Byers . Despite everything, she has not given up on romance. We are wishing her that she finally finds the man of her dreams!

Gail O’Grady As Mandi Now

Gail O’Grady As Mandi Now

Paula Marshall As Paula Then

When it comes to dating we can merely say that Alan is not a lucky person. Why? Because he assumes that he struck gold after meeting Paula in a nightclub. Later on, she later reveals to him that she was once married to a guy named Paul. She, later on, admits that she wants an open relationship and urges. Alan also goes out with his wife as well. This made the story very much complicated. As the story goes on, this does not go very well for both parties involved.

Paula Marshall As Paula Then

Paula Marshall As Paula Then

Paula Marshall As Paula Now

The television comedy show was not the first time that Paula Marshall appeared on the small screen. She guest starred on Superboy in 1991 with a young Clark Kent before being called Superman in 1991. Among other film in which she was also a cast are Murder in the First and The Mentalist. She also appeared in a film called We Love You, Sally Carmichael. She is now married to Danny Nucci, who played Fabrizio in Titanic.Marshall was married to actor Danny Nucci since 2003 with a daughter.

Paula Marshall As Paula Now

Paula Marshall As Paula Now

Tammy Lauren As Shannon Then

Alan again meets Shannon during the second wedding of Judith and Herb. As time went by, he later found out that she and Herb were already engaged. Shannon and Alan were both hung up on their exes and used each other to the point that it would both make them jealous at the ceremony. Shannon takes a step further by screaming out Alan’s name while the wedding is ongoing. The plan did not work out and neither of them wins back their ex. They both fail to accomplish their mission.

Tammy Lauren As Shannon Then

Tammy Lauren As Shannon Then

Tammy Lauren As Shannon Now

Aside from her Two and a Half Men appearance, Lauren had a long-term gig playing Maggie Sullivan in The Young and the Restless. The actress is not as popular and as successful as some of the other ladies on the list we may say. She is also a cast member of Madison Avery before she portrayed the role as Liz Foley in an episode of Criminal Minds in 2014. The actress has been married to an Israeli actor Guri Weinberg ever since 1997.

Tammy Lauren As Shannon Now

Tammy Lauren As Shannon Now

Justine Eyre As Gabrielle Then

Charlie’s house never lacks drama at all. . When he starts going out with Gabrielle, Alan learns that Charlie stole his high school girlfriend. This is the reason why he tries to steal Gabrielle. But then, he later ends up backpedaling and finds the situation very uncomfortable even though everything is going well. After going back home, he discovered that his brother was with his high school sweetheart once more. This makes him feel quite more unrelaxed.

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Justine Eyre As Gabrielle Now

This model and actress has some more television appearances after the said comedy sitcom. Justine. Like the other character on the list, her career didn’t make it big like their co stars who really shine, and she has not been very active in Hollywood after her stint on the show, but she made it be included in the cast of Mad Men, The Secret Life of the American Teenager, and CSI: Miami. Her last credit was from 2016. After all , she is happily married to screenwriter John Allen Nelson.

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Maggie Lawson As Ms. McMartin Then

Although Charlie is killed off, Alan, Jake, and Walden continue to keep up their flirtatious ways. When Walden and Alan are trying to adopt, they end up liking the social worker in the story. When they assigned Louis, Ms. McMartin realized that they lied about their application. Moreover, she ends up forgiving them and even dates Alan. In the end, however, she changes her mind and decides to move on to Walden.

Maggie Lawson As Ms. McMartin Then

Maggie Lawson As Ms. McMartin Then

Maggie Lawson As Ms. McMartin Now

She already had a great career even before she had appeared on the show. . Over the years, she appeared in The Great Outdoors, Angel From Hell, and Psych. On top of that, she played Juliet O’Hara in the 2017 movie adaptation of Psych. She also held a recurring role as Nathalie Flynn on Fox’s Lethal Weapon in 2019. The actress got engaged to Ben Koldyke of Mr. Robinson fame in November 2014 and married him in 2015. In early 2017 she filed for divorce from Koldyke.

Maggie Lawson As Ms. McMartin Now

Maggie Lawson As Ms. McMartin Now

Conchata Ferrell As Berta Then

Alongside his mother, Berta is the only other constant female character in the show. Her snappy interactions with Charlie and her position as a mother figure made her so popular with the fans that she remained on air even with Charlie’s death. Fun fact: Berta has at least an appearance in every single season of the sitcom.

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Conchata Ferrell As Berta Now

Conchata Ferrell’s talented performance as Berta seems to be the most memorable point in her career, having been nominated twice for the Outstanding Supporting Actress in a Comedy Series award at the Primetime Emmys and even gone on to the Broadway stage. She has recently reunited with fellow Two and a Half Men costar Ashton Kutcher and is working together on a TV show called The Ranch.

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Jenny McCarthy As Courtney Leopold Then

Charlie’s mom is going to get married to Courtney’s dad, but that doesn’t stop Charlie from dating the blonde bombshell. Alan somehow knows Courtney’s true nature and tries to warn his brother, but it wasn’t enough as Courtney was able to get Charlie to give her $50,000 and a Ferrari. Eventually, the two split as Charlie learns that Courtney and her fake dad were actually con artists!

Jenny McCarthy As Courtney Leopold Then

Jenny McCarthy As Courtney Leopold Then

Jenny McCarthy As Courtney Leopold Now

Jenny McCarthy was already a big star before joining the sitcom; she was a Playboy bunny and an MTV dating show host. She also once had a self-titled show and got married to Hollywood actor Jim Carrey, but they got a divorce in 2010. She has since married to Donnie Wahlberg, and they even got a reality show centered around them. Jenny is also an activist, an author, and a screenwriter.

Jenny McCarthy As Courtney Leopold Now

Jenny McCarthy As Courtney Leopold Now

Teri Hatcher As Liz Then

Liz’s appearance only further complicates the relationship between her sister Judith and Alan. She and Charlie got together at the wedding, but the latter does not recall anything. Having gotten over Charlie, she attempts to strike a relationship with Alan, which obviously hurts her sister. Alan revealed later on that before he and Judith dated, he wanted Liz in the first place! Thankfully, nothing eventually happened between them.

Teri Hatcher As Liz Then

Teri Hatcher As Liz Then

Teri Hatcher As Liz Now

Teri Hatcher’s successful career includes her appearance in Tomorrow Never Dies, Lois & Clark: The New Adventures of Superman, and Desperate Housewives, with the latter letting her bag a Golden Globe and three SAGs. She also made an appearance in Supergirl and The Odd Couple, but her love life has not been as fruitful.

Teri Hatcher As Liz Now

Teri Hatcher As Liz Now

Jaime Pressly As Tammy Then

When Jake introduced Tammy, his girlfriend, to his dad, it shows that father and son seem to be quite alike. Tammy runs a tattoo parlor and is a mother of three, so there must be some difficulty between her and Jake because of their backgrounds and age gap, right? Apparently, the reason for their break up was because Jake dated Tammy’s daughter Ashley. Tammy also gets down with Walden as well! This is truly a complicated relationship.

Jaime Pressly As Tammy Then

Jaime Pressly As Tammy Then

Jaime Pressly As Tammy Now

Bridget was introduced to the show when Ashton Kutcher takes on the role of Charlie Sheen. Walden had a rough time after the divorce and Alan finds him trying to take his life. It was revealed that Bridget thought that Walden is too immature, but she then attempts to get back to him when the latter began going out with Zoey.

Jaime Pressly As Tammy Now

Jaime Pressly As Tammy Now

Judy Greer As Bridget Schmidt Then

Bridget was introduced to the show when Ashton Kutcher takes on the role of Charlie Sheen. Walden had a rough time after the divorce and Alan finds him trying to take his life. It was revealed that Bridget thought that Walden is too immature, but she then attempts to get back to him when the latter began going out with Zoey.

Judy Greer As Bridget Schmidt Then

Judy Greer As Bridget Schmidt Then

Judy Greer As Bridget Schmidt Now

Judy Greer is one very talented actress, having worked on multiple films such as 27 Dresses, 13 Going on 30, The Wedding Planner, What Women Want, and Love & Other Drugs, as well as being the casting director of the film Entourage. She had also released a book, called I Don’t Know What You Know Me From: Confessions of a Co-Star in 2014.

Judy Greer As Bridget Schmidt Now

Judy Greer As Bridget Schmidt Now

Sophie Winkleman As Zoey Hyde-Tottingham-Pierce Then

Zoey’s the one who helped Walden regain his desire to get back together with Bridget. The British beauty was able to capture the man’s heart almost instantly, but it wasn’t for long as she turned down his proposal; Walden eventually found out that Bridget was going out with another man while they were dating. As revenge, Walden gave a birthday gift to Bridget’s daughter… in the form of a vicious dog.

Sophie Winkleman As Zoey Hyde Tottingham Pierce Then

Sophie Winkleman As Zoey Hyde-Tottingham-Pierce Then

Sophie Winkleman As Zoey Hyde-Tottingham-Pierce Now

Married to Lord Frederick Windsor, one of the Queen’s cousins, Sophie Winkleman could be one of the fanciest cast members of the show! Even as a member of the British royal family, she continues her career as an actress; appearing in shows like 2018’s Thrust, CSI: Miami, and Milo Murphy’s Law.

Sophie Winkleman As Zoey Hyde Tottingham Pierce Now

Sophie Winkleman As Zoey Hyde-Tottingham-Pierce Now

Diora Baird As Wanda Then

Diora Baird made a memorable mark in the show despite having only appeared in one episode! Her career began as a model for Guess and later for Playboy, but she had gained more attention after appearing in the show. One would also notice her from Wedding Crashers as well.

Diora Baird As Wanda Then

Diora Baird As Wanda Then

Diora Baird As Wanda Now

Diora Baird’s career continued after the show, and has appeared in the website Funny or Die, which mostly consists of funny videos. She also starred in an adult film in 2014 called The Ugly Life of a Beautiful Girl, and is a recurring character in Cocked. Recently, she had shared that she’s dating female comedian Mav Viola.

Diora Baird As Wanda Now

Diora Baird As Wanda Now

Krista Allen As Olivia Pearson Then

Charlie’s life takes a turn when he visits a dinner party hosted by his own mom, as he finds out that his mother’s boyfriend happened to be the father of Olivia, who he once dated! This realization makes for a very, very uncomfortable dinner session. And when things can’t get any worse, Evelyn’s boyfriend dumped her for someone else younger!

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Krista Allen As Olivia Pearson Now

Krista Allen enjoys a great acting career ever since starting off in the 90’s, first appearing in the soap opera Days of Our Lives, and appeared in other films such as Final Destination and Anger Management. She recently also snagged a role in Best Mom and Eleven Eleven.

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Kelly Stables As Melissa Then

A lot of female characters in the show not only dated Charlie but Alan as well! Take Melissa, who’s Alan’s secretary, for example. First dating Charlie, she then gets to dating Alan, with the latter yet again lying about his life. At first, their relationship is steady despite Alan and Lyndsey living together in the same roof, but it, unfortunately, went sour as Melissa askes Alan for health insurance and a raise.

Kelly Stables As Melissa Then

Kelly Stables As Melissa Then

Kelly Stables As Melissa Now

Kelly Stables continued her acting career after her appearance on Two and a Half Men. She shared her voice acting for W.I.T.C.H. and Cloudy with a Chance of Meatballs, as well as working on Malibu Dan the Family Man, Superstore, No Tomorrow, and Horrible Bosses 2.

Kelly Stables As Melissa Now

Kelly Stables As Melissa Now

Heather Locklear As Laura Then

Charlie’s less-than-good tastes on picking the ladies could be attributed as to why he chose to pursue Laura. She was Alan’s lawyer while the latter was going through with a divorce. The relationship turns south when Charlie promises to be there for her, whenever she needed him, which eventually ends in a breakup. As her act of revenge, Laura ruins Alan’s divorce settlement, forcing him to look for a new lawyer.

Heather Locklear As Laura Then

Heather Locklear As Laura Then

Heather Locklear As Laura Now

Heather Locklear holds a dominating presence during the 80’s and 90’s, best known for her roles in Spin City and Melrose Palace, with her recent projects being Too Close To Home, Fresh Off The Boat, and Franklin & Bash. She also happens to be on the tabloids regularly mostly because of her public divorce or her health problems.

Heather Locklear As Laura Now

Heather Locklear As Laura Now

Kimberly Quinn As Donna Then

During a double date, Donna and Alan looked like a good couple… and then Alan got bored with her. Asking Charlie for advice, he received instructions to let her down easily, which was good news for him, but not so much for Donna, who doesn’t take it too well!

Kimberly Quinn As Donna Then

Kimberly Quinn As Donna Then

Kimberly Quinn As Donna Now

Kimberly Quinn’s best-known performances include playing as Gretchen in Terriers, and Tess Masterson in Twisted. She also appeared in numerous other works such as Nash Bridges, Suddenly Susan, Diagnosis: Murder, CSI: NY, NYPD Blue, and Without A Trace. She’s now married to producer Theodore Melfi.

Kimberly Quinn As Donna Now

Kimberly Quinn As Donna Now


Denise Richards As Lisa Then

Lisa’s one of the lucky few people Charlie calls as his girlfriend and even lived in his house at one point! But when things get serious, Charlie panics and breaks up with Lisa. She later got married but promised Charlie to call him in case a divorce happened. Quite a way to start off a marriage, huh? Well, the divorce did happen, and they came back once more, but it ends once again with them splitting up.

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Denise Richards As Lisa Now

Denise Richards plays the role of Lisa, who happens to be the wife of the actor during that time, hence their chemistry. They were husband and wife from 2002 to 2006, with two daughters. It was a difficult time when they called it quits, especially when it involves Charlie’s battle against addiction. But, after lawsuits and accusations, things have finally settled between them.

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Kristin Dattilo As Cindy Then

Cindy’s not impressed by Charlie’s charm, and Jake really likes the girl, having even developed a crush on her! In a surprising turn of events, Judith and Cindy met, and they made a bond over their daddy issues! Even Alan was suspicious and wonders if the two ladies were actually dating.

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Kristin Dattilo As Cindy Now

Kristin Dattilo started off her career by working on The Chris Isaak Show for four years and has appeared in numerous TV shows like Beverly Hills, 90210, CSI, Grounded for Life, Dexter, and Veronica Mars. She’s also seen in Aerosmith’s music video of “Janie’s Got a Gun”. She married Jason Keller in 2005 and now has two kids as well.

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Courtney Thorne-Smith As Lyndsey McElroy Then

Lyndsey plays a big part in the seventh season as Alan’s love interest, but the two had an on-and-off relationship. They just have so many splits and makeups that it’s hard to track them all! It all started when Jake befriends her son, but Lyndsey seems to have a drinking problem and even attempts to get it down with Walden.

Courtney Thorne Smith As Lyndsey McElroy Then

Courtney Thorne-Smith As Lyndsey McElroy Then

Courtney Thorne-Smith As Lyndsey McElroy Now

For five years, Courtney Thorne-Smith gave Lyndsey McElroy life to the show. Her previous gig was in Ally McBeal from 1997 to 2002. Her career slowed down for a while as she focused on family, but she has made a comeback in Fresh Off The Boat and Robot Chicken.

Courtney Thorne Smith As Lyndsey McElroy Now

Courtney Thorne-Smith As Lyndsey McElroy Now

April Bowlby As Kandi Then

Kandi and Alan got hitched in Vegas, which came as a shock to many! She even moved with Alan after, but things were going south after she got a role in Stiffs, causing her to leave Alan eventually.

April Bowlby As Kandi Then

April Bowlby As Kandi Then

April Bowlby As Kandi Now

April Bowlby continued acting after the show, deciding to switch from red hair to blonde. She worked in shows such as Drop Dead Diva, How I Met Your Mother, and the Big Bang Theory, and she also worked on movies like Love Me Or Else.

April Bowlby As Kandi Now

April Bowlby As Kandi Now

Brooke Shields As Danielle Stewart Then

Knowing about Danielle’s past, Charlie attempts to introduce her to Alan in the hopes that the latter would get out of his house. But after some conversation, it seems that Charlie and Danielle were a better match! This resulted in a fight between brothers, and the end decided to kick Danielle out, preferring to stick to each other instead.

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Brooke Shields As Danielle Stewart Now

Brooke Shields began her career as a child star, making her a long-runner in the industry before her appearance in the show! Before her big break, she used to model, and do various commercials. Now in her fifties, she also worked in other projects such as Hannah Montana, Law & Order: Criminal Intent, and The Middle, with a recurring part in Law & Order: Special Victims Unit. The lovely brunette is married to Chris Henchy, and they both have two children.

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