Two and a Half Men was an extremely popular sitcom that ran from 2003 to 2015. A somewhat modern take on the classic “odd couple” dynamic, the show initially focused on the relationship between two brothers, the suave and irresponsible Charlie (played by Charlie Sheen) and the high-strung Alan, (played by Jon Cryer), whose main concern is raising his mischievous son Jake (played by Angus T. Jones). Audiences loved the trio’s charming and bawdy humor, as the two men navigated their romantic lives, while the pint-sized half-man their co-parented navigated puberty.
Despite its incredible appeal, the show eventually gained negative media attention after Sheen was fired due to a publicized feud with one of the producers, while also displaying a host of very erratic public behavior. At the time, his termination was believed to spell the end of the sitcom. But the show bounced back, adding the character of Walden (played by Ashton Kutcher), Alan’s goofy and affable best friend.
While the storylines changed and new characters were introduced, one common thread throughout all 12 seasons was the amount of women that Sheen’s character was linked to. Over the years, Charlie dated and romanced a variety of women, played by some of Hollywood’s most talented and stunning leading ladies.
Although the show was called Two and a Half Men, it would not have been nearly as funny or entertaining without the addition of the female characters. During the show’s run, tons of women passed through Charlie’s beach house and without them, the storylines would not have been quite as exciting. Audiences tuned in week after week to see which woman Charlie would date next and they often added an element of drama and sometimes outright insanity to the two and a half men’s lives. The relationships that Charlie and Alan had (or didn’t have, in Alan’s case) helped audiences better understand their characters.
Whether you were rooting for Charlie to end up with a certain girlfriend or waited for him to finally get his comeuppance, the ladies who were (mostly) introduced as his paramours definitely left an impression, and made us wonder where their lives have taken them. So put on your comfiest Hawaiian shirt and join us in a walk down Memory Lane, as we check out the most memorable women to appeared on the show, and see what they are up to today.
Emmanuelle Vaugier as Mia | Then
Vaugier played a dance teacher on the show named Mia who has no interest in Charlie until he claims Jake, his nephew, enjoys dancing. Mia agrees to go on a date with Charlie but only if he gives up eating meat, smoking, and drinking. Of course, Charlie agrees but continues to do all of those things behind her back. She ultimately leaves him but comes back in a later episode to ask to use his sperm to have a baby. The two almost get married but Mia ends it after Charlie says his brother won’t be moving out of his beach house.
Emmanuelle Vaugier as Mia | Now
Two and a Half Men was great for Vaugier’s career as she continued to get acting jobs after her appearance on the show. She has worked on shows such as Lost Girl and Mistresses, as well as television movies such as Destruction Los Angeles and Washed Away. Vaugier is now 41 and continues to pursue her acting career. She is currently filming a movie titled Masks Don’t Lie.
Denise Richards as Lisa | Then
Before Alan moved into Charlie’s beach house, Charlie was living with his girlfriend Lisa. He ends up breaking up with her because he does not want to commit. Lisa eventually tells Charlie that she has plans to get married and Charlie tries to win her back by pretending that he has become a family-oriented guy. Lisa and her husband end up divorcing and she takes Charlie back. True to form, though, Charlie again ends things with Lisa because of his fear of commitment.
Denise Richards as Lisa | Now
Denise Richards, who played Lisa, was actually married to Charlie Sheen in real life. Richards and Sheen were married from 2002 until 2006 and they had two daughters together named Sam and Lola. After several tumultuous years of marriage, Richards filed for a divorce from Sheen while pregnant with their second child. She later adopted another daughter, named Eloise. Today, Richards is 47 and is still working as an actress. Her movie called 1st Born is in post-production.
Melanie Lynskey as Rose | Then
Rose was a fan favorite, as she was one of the most curiously behaved women Charlie had ever dated. The two were only together for one night, but that one time fling led Rose to begin stalking Charlie. Later on in the show, Charlie and Rose actually get engaged and run off to Paris together. However – spoiler alert – Charlie seemingly dies before they tie the knot. During the series finale, however, it’s discovered that not only is Charlie alive, but that Rose has been holding him captive for four years.
Melanie Lynskey as Rose | Now
Even before she appeared on our screens as Charlie’s stalker, Lynskey has been making appearances in many other shows and films. She has appeared in Sweet Home Alabama and Heavenly Creatures, and is now filming two new shows, one titled Castle Rock and one titled Sunshine and Stephen King. The New Zealand native was married to actor Jimmi Simpson until the couple divorced in 2014.
Jennifer Taylor as Chelsea Melini | Then
Chelsea Melini had the great honor of being the very first woman on the show that Charlie ever admitted he loved. When he first says it, he claims that it was an accident. However, he admits to her that he really did mean it later on. While Chelsea started out as just another fling for Charlie, their relationship ultimately turned serious. Charlie goes far to get Chelsea to admit that she loves him too by proposing to her. Unfortunately, she ends up leaving him for Alan’s lawyer.
Jennifer Taylor as Chelsea Melini | Now
Jennifer continued to act after her appearance on Two and a Half Men and was subsequently involved in other shows and films. Most recently, she appeared on the show Shameless, but she can also be seen in shows such as NCIS and Mom, starring Anna Faris, in addition to films such as the made-for-TV thriller Stalked by My Mother and family flick Arlo: The Burping Pig. The actress is 45 and married to songwriter Paul Taylor. The couple have two children together.
Holland Taylor as Evelyn Harper | Then
Evelyn Harper was arguably one of the funniest characters on the show and she played Alan and Charlie’s neglectful mother. Evelyn had a strained relationship with both of her sons and they both tried to see as little of her as possible. However, when they did end up meeting, it made for great TV. She was known for getting involved with older men with money and then making sure to inherit their assets after their passing.
Holland Taylor as Evelyn Harper | Now
Today, Taylor is in her mid seventies but she is not letting her age stop her from doing her thing. Harper is continuing to get acting jobs in Hollywood and has appeared on other televisions shows including The Orville and Hollywood Mom. Taylor recently got cast in a big role in the show Mr. Mercedes where she plays the character Ida Silver. Taylor’s age is not affecting her dating life either as she is in a relationship with Sarah Paulson, who is in her forties.
Marin Hinkle as Judith Harper-Melnick | Then
Judith was Alan’s ex-wife on the show and the mother of their son Jake. The couple’s marriage was a very cold one, which led to their divorce. Judith was infamous for spending her alimony cheques from Alan on plastic surgery and luxurious purchases. Later on in the series, Judith gets married to Jake’s doctor, Herb Melnick, which results in Alan no longer having to pay alimony. That marriage does not last either, though, as Herb is unfaithful to Judith with his secretary.
Marin Hinkle as Judith Harper-Melnick | Now
Marin has continued to have a successful acting career and can be seen on the dramatic series Madam Secretary on CBS. She also appeared as Dr. Miller in Speechless and as Christine Lonas on Homeland. Hinkle is now 51 and continuing to get acting jobs. She has just wrapped filming on a movie called Before/During/After. While Hinkle could not catch a break with her relationships on Two and a Half Men, in reality she is happily married to Randall Sommer.
Courtney Thorne-Smith as Lyndsey McElroy | Then
Lyndsey kept popping up on the show after she began a relationship with Alan in season 7. Their relationship was quite tumultuous as it was very much on and off. We cannot count how many times these two broke up and reunited. Lyndsey’s son Eldridge was best friends with Alan’s son Jake and she was also known for being a heavy drinker. This led her to lust after other men including Walden, Ashton Kutcher’s character.
Courtney Thorne-Smith as Lyndsey McElroy | Now
Thorne-Smith played the role of Lyndsey for five years on Two and a Half Men the actress has slowed down her work in show business. The 50-year-old recently appeared in ABC’s new comedy show Fresh Off the Boat and has also offered her voice to the animated series Robot Chicken. When she’s not acting, the Ally McBeal and Melrose Place alum enjoys spends her time with her son Jacob and her second husband, author Roger Fishman.
Allison Janney as Beverly | Then
Beverly first found her way to Charlie’s beach house when she connected with Alan on a dating website. In order to impress his lady friend, Alan claims Charlie’s house is his but admits it’s really his brother’s house after Beverly opens up to him about her past marriages. Luckily, she doesn’t mind when he finally confesses. It does not, however, turn out well for Alan, who we see tied up by Beverly when Charlie walks into his room.
Allison Janney as Beverly | Now
You may recognize Allison Janney from one of her many television or movie roles. Janney is probably best known for her role on The West Wing, and she has continued to work in Hollywood for years since then. She has appeared in hit movies like Juno, Hairspray, and The Girl on the Train. Nowadays, Janney can be spotted on the CBS show Mom where she plays Anna Faris’ mother. The role has been great for Janney as she earned an Emmy for her work on the show.
Brooke Shields as Danielle Stewart | Then
Charlie was trying to get Alan to move out of his house and came up with a scheme to set him up with Danielle to get him out. Danielle was with many men in the past but thought it was time for her to settle down for a lasting relationship. However, when Danielle confides in Charlie about her past, Charlie decides he wants to be with her instead. The two brothers argue over who gets to date her, which causes her to make up her own mind, and leave.
Brooke Shields as Danielle Stewart | Now
Acting since she was a little girl, Brooke Shields was The IT girl in the ’70s and ’80s, with roles in Pretty Baby and The Blue Lagoon, as well as being Calvin Klein’s muse. Since her appearance on the Two and a Half Men, she has appeared in many shows and movies, such as The Other Guys and Army Wives. Now in her early fifties, Shields is married to producer and screenwriter Chris Henchy, and they have two children together.
Jenny McCarthy as Courtney Leopold | Then
Courtney met Charlie after her father got engaged to his mother. The two begin to see each other even though Alan warns his brother that Courtney has some sociopathic tendencies. Alan is proven right after she convinces Charlie to get her a Ferrari and give her $50,000. Charlie eventually proposes to her but does not go through with the marriage because he finds out that her real name is Sylvia and she and her “father” are actually con-artists.
Jenny McCarthy as Courtney Leopold | Now
Jenny McCarthy was in the spotlight long before she appeared on TAAHM. She was once a Playboy bunny and was the star of her own television show back in the 1990s. McCarthy notably dated comedic actor Jim Carrey but the two eventually split. McCarthy has a son with autism and she advocates for awareness of the condition. She has also made some of her controversial views very public such as being against giving disease preventing vaccinations to children.
Jeri Ryan as Sherri | Then
After years of changing the women he’s dating the way most of us change the channel, Charlie finally met his match, in the form of the voluptuous Sherri. Like Charlie, Sherri was used to trading in her dating partners, only in her case, it was men. Ironically, this proved to be too much for Charlie, and after she tried to play hard to get, their time together came to an end. Sherri then ran into the arms of Alan but that did not last, either.
Jeri Ryan as Sherri | Now
Just as stunning as she was when “dating” Charlie, the German-born Ryn is now 49 and is still appears on television following her stint on Two and a Half Men. She has a long list of shows on her résumé, including Major Crimes, Body of Proof, Star Trek, and Helix. She can also be seen on the series created by Amazon Prime called Bosch. Ryan has two children with her French chef husband, Christophe Eme.
Kimberly Williams-Paisley as Gretchen Martin | Then
Alan’s on-again-off-again girlfriend Lindsey eventually got engaged to another man, Larry. Larry’s sister Gretchen then began dating Alan after he came up with an alter-ego and began acting differently. Alan gets very into his new identity and even claims that his son’s apartment is actually his. Gretchen eventually breaks up with Alan after she discovers his lies, and tells Alan that her ex-husband constantly lied to her.
Kimberly Williams-Paisley as Gretchen Martin | Now
Kimberly had a fair bit of acting experience before appearing on Two and a Half Men, already being famous for her role in the hit movie Father of the Bride. She also appeared on According to Jim for 8 years. Her latest project is a festive film titled The Christmas Train, which is in post-production.Williams-Paisley got her hyphenated last name from being married to country singer Brad Paisley. The good looking couple have two kids together.
Judy Greer as Bridget Schmidt | Then
When we are first introduced to Ashton Kutcher’s character, Walden, we found out that he is divorced from Bridget. Walden loves her so much that he even tries to take his own life because she won’t take him back. Bridget believes Walden is too immature and refuses to get back together with him until she finds out he is dating Zoey. She comes to his beach house and begs for him to take her back but Walden instead offers to finalize their divorce.
Judy Greer as Bridget Schmidt | Now
Judy has quite the varied résumé and has had many titles besides actress. She switched roles to behind the scenes when she was a casting director for the movie version of Entourage. She has also lent her voice to animated shows such as StoryBots and Archer. When she is not doing voice-overs, she is in front of the camera and was recently cast in the remake of the hit movie, Halloween.
Sophie Winkleman as Zoey Hyde-Tottingham-Pierce | Then
Besides having an incredibly long last name, the British native Zoey was known as Walden’s serious girlfriend after he divorced from Bridget. Zoey dated Walden for two seasons until the single mother rejected his marriage proposal. Walden discovers that Zoey was in fact dating another man and decides to plot his revenge, by gifting Zoey’s daughter a vicious dog for her birthday to get back and his former lover.
Sophie Winkleman as Zoey Hyde-Tottingham-Pierce | Now
You may be surprised to know that this British beauty is actually royalty as she tied the knot with Lord Frederick Windsor. Windsor is a distant cousin of Queen Elizabeth, which means that Winkleman is royal by marriage. Since her time on Two and a Half Men, Winkleman has been voicing a character on the show Milo Murphy’s Law. She is now appearing on camera again and is currently filming for a new show title Trust, which also features Donald Sutherland and Hilary Swank.
Ming-Na Wen as Linda Harris | Then
Charlie and Linda were introduced after Alan planned a double date involving his brother. While Charlie thought that Linda was beautiful, she was turned off by his personality and all around rudeness. Comedy ensues when Linda turns out to be Charlie’s judge after he is charged with a DUI. Eventually, though, Linda decides she had judged him too quickly, and agrees to give Charlie another chance – until he embarrasses her at a ceremony where she to receive an award.
Ming-Na Wen as Linda Harris | Now
If you get the feeling that you have heard the name Ming-Na Wen it might be because she was the voice of the Disney character Mulan. Besides that notable role, Wen starred in the television show ER and has had roles on other shows such as Eureka and SGU Stargate Universe. Nowadays you can find Wen acting in the sci-fi series Agents of S.H.I.E.L.D. She is married to Eric Michael Zee, and the couple have two children together.
Heather Locklear as Laura | Then
While Alan and Judy were going through their divorce proceedings, Laura was employed by Alan as his lawyer. However, Charlie ruined this when he slept with her and promised that he would make himself available to her whenever she wanted. Charlie obviously broke his oath to Laura and she exacted her revenge by ruining the divorce settlement between Judith and Alan. In the end, Alan let her go and hired a new lawyer.
Heather Locklear as Laura | Now
Before she made her appearance as Laura on TAAHM, Locklear was already an accomplished television actress. Her most notable roles were on Melrose Place and Spin City. Locklear has gone through a very public divorce and issues with her health but she has gotten her life back on track, and has even appeared in other shows such as Franklin & Bash. Today, she is now acting on Tyler Perry’s show Too Close to Home.
Gail O’Grady as Mandi | Then
Alan was married to a woman named Kandi for awhile and Kandi’s mother was, as it turns out, is Mandi. In one episode, Mandi goes looking for Kandi and ends up at Charlie’s beach house. She gets introduced to Charlie and the two end up spending the remainder of the day with each other. We also find out that due to Kandi and Mandi looking very similar, strangers would often mistake them for sisters, and not mother and daughter.
Gail O’Grady as Mandi | Now
Before she appeared on TAAHM, Gail O’Grady was featured on the television show American Dreams. Since playing Mandi on the show, she has appeared in other projects such as Ms. Fields and Revenge. While O’Grady’s career is going well, her personal life is a bit more tumultuous as she has tied the knot no less than 6 times. Her last marriage ended in 2008 and was to actor John Stamatakis. She had one son with ex-boyfriend Chris Byers.
Paula Marshall as Paula | Then
Paula and Alan got along right away after their first meeting in a nightclub. Shortly after, Paula reveals that she was once a man whose name was Paul. This does not seem to bother Alan and the two begin seeing each other. The story gets weird after Alan meets Paula’s ex-wife Rachel and Paula tells Alan that she wants to be in an open relationship. Alan then begins dating Rachel and Paula sees them kissing each other. Paula and Rachel decide to give it another go and they both break up with Alan.
Paula Marshall as Paula | Now
Paula Marshall has had many other acting roles since TAAHM and as appeared in House, Law and Order, Murder in the First, Switched at Birth, and The Mentalist. Her most recent appearance was in the movie We Love You, Sally Carmichael! Marshall is married to Danny Nucci who had his big break acting in the film Titanic as Fabrizio. The two have a daughter named Maya.
Missi Pyle as Miss Pasternak | Then
No woman was off limits for Charlie, not even Jake’s elementary school teacher. When the two began dating, Jake’s life turned around for the better as she started giving him good grades. When Charlie finds out she has a mental problem, he dumps her and a couple seasons later we discover that she is no longer allowed to be a teacher, and that she is working as a dancer and lives in a motel. Charlie offers her a job as Jake’s tutor and she turns to religion. She even proposes to Charlie. Of course, Charlie eventually ends their relationship.
Missi Pyle as Miss Pasternak | Now
Missi Pyle has continued her career as a television actress since her appearance on TAAHM. The Texas-born actress has appeared on Inside Amy Schumer and Sing it. She has also offered her acting talents to movies such as The Artist and Gone Girl and will be appearing in the upcoming movie release of Jumanji. She also has many other projects on the horizon that are currently in post-production. The actress is twice divorced and is taking a break from marriage.
Kimberly Quinn as Donna | Then
Remember that blind date where Charlie met Linda Harris? That date is when Donna and Alan were introduced. Everything was going well with the couple until Alan decided to end it because he was bored of her. Alan is nervous and does not want to hurt Donna’s feelings but Charlie gives him advice about how to let her down gently but it does not seem to work as Donna becomes hysterical when Alan tells her it’s over.
Kimberly Quinn as Donna | Now
Quinn continues to work as an actress until today and acts in multiple television shows including Twisted and the Netflix series Gypsy. Quinn is married to a producer named Theodore Melfi. Melfi is well-known for his work on movies such as St. Vincent and Hidden Figures. Nepotism certainly works in Hollywood as Quinn got an acting role in St. Vincent and she played the role of Nurse Ana.
Tammy Lauren as Shannon | Then
Alan was introduced to Shannon at the wedding of her ex-wife Judith. Shannon tells Charlie that she was once engaged to Judith’s new husband Herb and the two get romantic in the coatroom at the wedding. In an attempt to make their former lovers jealous, the two pretend to get intimate. Shannon even screams out Alan’s name, making a scene amongst the wedding guests. Unfortunately, this relationship did not last too long.
Tammy Lauren as Shannon | Now
Before her appearance on TAAHM, Lauren was a regular on The Young and the Restless, which is a long-running soap opera. After her episode on TAAHM, she continued to act as the detective Maggie Sullivan on the soap opera. Her acting jobs seemed to have dwindled as she only appeared on a single episode of the show Criminal Minds which aired in 2014. Maybe Lauren is focusing on her marriage to Guri Weinberg who is also an actor.
Justine Eyre as Gabrielle | Then
Gabrielle dated Charlie, and after Alan finds out that Charlie stole a girlfriend from him in high school, he attempts to take revenge and steal Gabrielle. His plan actually works and he ends up with Gabrielle but he decides to end it, saying that the situation was “uncomfortable.” When he goes home, he discovers that Charlie is with his high school girlfriend named Charity. Alan then says to Charlie that they are even.
Justine Eyre as Gabrielle | Now
Justine has not made it as big as some of the other actresses on our list but she has made a few appearances. The Canadian actress has appeared on shows like Mad Men, The Secret Life of the American Teenager, and CSI: Miami. She has not acted in anything since 2016 but hopefully she will make a return into show business. Eyre is married to John Allen Nelson who is a screenwriter.
Maggie Lawson as Ms. McMartin | Then
When Walden and Alan decide to adopt a child, Ms. McMartin is assigned to be the pair’s social worker. The “couple” are given a boy named Louis but the adoption does not last too long as McMartin discovers that they were deceitful. She goes to take Louis back but lets him stay after she sees how close he is with Alan and Walden. McMartin dates Alan until she leaves him and begins a relationship with Walden.
Maggie Lawson as Ms. McMartin | Now
Maggie has had a lot of success as an actress in television and she has appeared in other shows such Psych, Angel From Hell, and The Great Indoors. Maggie is gearing up to play Juliet O’Hara in the movie version of Psych, which is set to be released at the end of 2017. Maggie is married to fellow actor Ben Koldyke who is best known for acting in the NBC series, Mr. Robinson.
Krista Allen as Olivia Pearson | Then
Olivia was a past girlfriend of Charlie’s but they reunited in the first season when Charlie goes to his mother’s house. Evelyn had her boyfriend at the time over as well as his daughter, who just happens to be Olivia. Once it was discovered that Charlie and Olivia were once an item, they start to argue, and Olivia throws her drink on face. Evelyn’s boyfriend eventually leaves her for a younger woman.
Krista Allen as Olivia Pearson | Now
When Kirsta Allen appeared on TAAHM, she was not new to show business as she has been acting since the 1990s. Her breakout role was on the soap opera Days of Our Lives, which has been running for 53 seasons. Allen also made it onto the big screen, appearing in films like The Final Destination and Anger Management. Allen will be featured in an upcoming movie called Best Mom as well as a comedy film called Eleven Eleven.
Teri Hatcher as Liz | Then
Liz is Alan’s ex-wife Judith’s sister. Charlie does not remember but he and Liz got together at Alan and Judith’s wedding. She appears for the first time on the show at Jake’s birthday party. Judith gets upset when Liz hits on Alan and they begin to fight. We then find out that before Alan asked out Judith, he asked out Liz. In a comical turn of events, Liz takes Alan to a room and Judith takes Charlie but nothing happens with either couple.
Teri Hatcher as Liz | Now
Teri Hatcher made it big in Hollywood shortly after her appearance on TAAHM as she starred in the drama show Desperate Housewives, which she worked on for eight years, Since then, Hatcher has made a couple of television appearances on Supergirl and The Odd Couple. Hatcher has been through two divorces and is now enjoying her single life in Hollywood. Her latest project Madness in the Method is currently in post-production.
Kristin Dattilo as Cindy | Then
Cindy was famous for being one of the very few women that Charlie could not get into bed with him. Jake is introduced to Cindy and quickly develops a crush on her. Jake ends up drawing one of her…assets for a school art project. Jake’s mother Judith meets Cindy and they bond over their tumultuous relationships with their respective fathers. They start doing everything together, which leads Alan to believe that the two are dating.
Kristin Dattilo as Cindy | Now
Datillo has been married to her husband Jason Keller since 2005 and the couple have two children together. After her appearance on TTAHM, Dattilo started getting a lot more roles and appeared on television shows such as Dexter and Southland. The actress took some time off from acting to be a mother when she began writing and is now developing multiple projects in entertainment. She made a return to acting and appeared in a comedy movie in 2016.
Liz Vassey as Kate McLaughlin | Then
Charlie is introduced to Kate at Jake’s soccer game who is their with her child that she is raising by herself. At first, Kate laughs at Charlie since he is drinking at a kids soccer game but they eventually start talking and she agrees to go out him. Kate appeared again on TAHHM but this time as Michelle who is Charlie’s dermatologist. She comically removes a mole off of Charlie’s behind and the two begin to date until Michelle ends things, especially after she starts getting suspicious that Charlie is in love with another woman.
Liz Vassey as Kate McLaughlin | Now
The casting director at TAHHM must have really loved Liz Vassey as she got cast in the show for two different roles. Since her time on the sitcom, Vassey has appeared on a couple other television shows such as Nikki & Nora: The N&N Files and Riley Parra. Vassey is most well-known for her role on CSI where she played Wendy Simms for five years straight. She has been married to her husband David Emmerichs since 2004.
Paget Brewster as Jamie Eckleberry | Then
Jamie knew Alan and Charlie since she was a little girl, however, they remembered her as a chubby and unattractive child and had a had a harsh nickname for her, Eckleberry Hound. Obviously, Jamie grows up to be a very beautiful woman. Both brothers attempt to hit of Jamie but she gets the last laugh and rejects both Alan and Charlie and reminds them how awful they were to her when she was young.
Pagent Brewster as Jamie Eckleberry | Now
Paget has quite the acting résumé and has appeared in several television shows and projects over the years. She even appeared on the hit show Friends where she had the honor of dating Chandler and Joey. She has acted in shows like Community, Criminal Minds, Grandfathered, Another Period, and voices multiple characters on the animated show American Dad. Her latest project is the horror film, The Witch Files, which is in post-production.
Rachel Cannon as Chloe | Then
Chloe dated Charlie for a short time but he was trying to get away from her the entire time. When a handyman comes to Charlie’s beach house to repair his deck, Chloe starts hitting on him, which causes Charlie to get jealous. He starts showing interest in Chloe and shows up to the handyman’s house dressed in a ‘hip’ way. He tries to win Chloe back and even attempts to bribe the handyman and ultimately fires him over the whole situation.
Rachel Cannon as Chloe | Now
You may not know Rachel Cannon’s name but you have definitely seen her face on many of your favorite TV shows. Cannon has appeared in shows such as Mad Men, The Big Bang Theory, Ghost Whisperer and Underemployed. Cannon has gotten mostly small roles in the past but you can now catch her in a bigger part on the ABC comedy show, Fresh Off the Boat. Hopefully she’ll get cast in a leading role in the near future.
Sara Rue as Naomi | Then
Naomi is introduced to Charlie and Alan as Berta’s daughter who is going through some challenges in her life. She is unemployed and pregnant and is forced to move in with Berta for financial and emotional support. She gets a crush on Alan and the two share a romantic moment right before she gives birth. She has a daughter named Brittany Pam and continues to see Alan but hides it from her mother. Berta eventually finds out about the relationship but to Naomi’s surprise, Berta says that Alan is the best guy she has ever been with. Naomi eventually leaves Alan when the father of her child returns.
Sara Rue as Naomi | Now
Sara Rue has had quite a successful career acting in television shows. She was in a number of shows including Popular, Will and Grace, The Division, and Less Than Perfect before her role on TAAHM. After her appearance on TAAHM she continued to land acting jobs on shows such as The Big Bang Theory, Eastwick, and Rules of Engagement. Most recently, Rue appeared on the show Bones, and you will be able to catch her on the Netflix version of A series of Unfortunate Events, which is set to be released in 2018.
Stephany Jacobsen as Penelope | Then
After Charlie dies, Walden steps in and purchases his beach house. Shortly after Walden moves in, a woman named Penelope shows up at the house and asks to see Charlie. Walden informs her of his death and Penelope is sad for a moment before she looks at Walden and quickly moves on from hearing the upsetting news. While Penelope is at the house, Walden’s ex-wife makes an appearance but Alan claims that Penelope is his girlfriend so Bridget does not get suspicious.
Stephany Jacobsen as Penelope | Now
Stephany Jacobsen was born in Hong Kong and has been acting since the early 2000s. Before she appeared on TAAHM, she was featured in shows such as Pizza, Home and Away, and Headland. She also had a consistent role on the remake of the show Melrose Place. Jacobsen took a short break from show business starting in 2014 after she appeared in Star-Crossed but is set to appear in the film Occupation, which is in post-production.
Jaime Pressly as Tammy | Then
Tammy is a mom of three who goes out with Jake during the 10th season of the show. Tammy has a unique look as she has tattoos all over. She even owns her own tattoo parlor called Tammy’s Tatties. Tammy is twice Jake’s age and Alan is not happy about the situation. The two break it off after Tammy finds out that Jake was romantically involved with her own daughter, named Ashley.
Jaime Pressly as Tammy | Now
Jamie has had many other acting roles besides her appearance on TAAHM. She has played roles in many films such as Not Another Teen Movie and I Love You, Man. Nowadays, Pressley is focusing on television and appeared on I Hate My Teenage Daughter. You can currently catch her on the CBS comedy show Mom alongside another TAAHM alumnus, Allison Janney. She was married to life mentor Simran Singh until 2011 and she has three children.
Miley Cyrus as Missi | Then
After Jake comes for a weekend leave from the Army, he meets and quickly falls in love with Missi. Right as Jake is preparing to head back to his base, Missi tells him that she already has a boyfriend. Missi and Jake plan to have a romantic night but it goes awry when Alan discovers that Jake has gone AWOL. Jake tells Missi he loves her, but she feels uncomfortable with the situation and tells Jake to go back to base.
Miley Cyrus as Missi | Now
Miley Cyrus is probably one of the most famous celebrities to ever appear on TAAHM and her appearance was enjoyed by many viewers. When Miley showed up on the show, she was already incredibly famous for her previous role as Hannah Montana and her singing career. The star is now 24 years-old and is continuing an upward climb in her career. She has received several awards and just released her newest album, Younger now.
Megan Fox as Prudence | Then
Prudence shows up at Charlie’s beach house in season one as Berta’s granddaughter. Berta tells Charlie she cannot leave Prudence alone and she has to drag her with her everywhere. All of the men, including Jake, are smitten with Prudence and she reveals that she plans to elope with her boyfriend Freddie in Las Vegas after she gets into a huge fight with Berta. Prudence’s plan is thwarted by her mother Cheryl Ann. On her way out of the house, Cheryl Ann of course notices and becomes attracted to Charlie.
Megan Fox as Prudence | Now
Everyone in the country knows who Mean Fox is and she has had major success in Hollywood. Soon after she appeared on TAAHM, Fox landed a role in the show Hope & Faith and was cast in the Transformer movie shortly after. She was in the next Transformers movie as well but was fired due to her alleged diva behavior. Fox most recently appeared on the hit comedy series New Girl, which stars Zooey Deschanel.
Conchata Ferrell as Berta | Then
Berta was probably one of the only woman to ever appear on TAAHM that Charlie did not get with. She offered a lot of comic relief as the maid who worked in Charlie’s home. She always pointed out the flaws in Alan and Charlie and was constantly making fun of them. Berta becomes Walden’s housekeeper after Charlie dies and she happily accepts her new job offer. Berta was a fan favorite of the show as she let her true feelings be known.
Conchata Ferrell as Berta | Now
While Conchata has moved on to other acting jobs since her time on TAAHM, the world will always know her as Berta. Conchata is now 74 and is still acting and appeared in the festive fantasy film, Krampus. She now plays Shirley on the comedy show, The Ranch. She is featured in the movie Deported which is yet to be released. The actress is married to an actor named Arnie Anderson and they have a daughter.
Kelly Stables as Melissa | Then
Melissa was once Alan’s secretary and first began dating Charlie until she started a relationship with Alan. After she and Charlie break up, Melissa forces Alan to give her health insurance along with a raise. They begin dating until she finds out that Alan is lying about renting a home. The two continue to be on and off and even get romantically involved while Alan is living with Lyndsey. Alan eventually decides to end their relationship for good over a text.
Kelly Stables as Melissa | Now
Kelly has landed a number of acting roles and was the voice of a character in the animated show W.I.T.C.H. She is still acting to this day, and has appeared in films like Horrible Bosses 2 as well as in the television shows Superstore and Malibu Dan the Family Man. The 39 year-old Stables has been married to Kurt Patino since 2005 and the couple have one son together.
April Bowlby as Kandi | Then
Kandi is a young a ditzy woman who finds her way into Charlie’s arms as well those of Alan’s and Alan’s former lawyer’s. She ends up marrying Alan in a Vegas wedding and moves in with him. She lands a part on a show titled Stiffs and eventually breaks up with Alan because he has hair on his nose and ears (and also because he was not interested in having children with her).
April Bowlby as Kandi | Now
Just like most of the other women on this list, Bowlby is still an active actress in Hollywood and has landed mostly small parts in other television shows after her appearance on TAAHM. She has appeared on shows like The Big Bang Theory, How I Met Your Mother, and Drop Dead Diva. Bowlby is currently filming a movie titled Love me or Else and is involved in a project called Reunion, which is in post-production. She is also famous for having dated the well-known singer Josh Groban.