Two and a Half Men was well known for the unlucky in love men who tried to win the hearts of many, many women. Where are all those ladies that Charlie, Alan, Walden, and even Jake, tried to win the hearts of?
Jennifer Taylor as Chelsea Melini | Then
Chelsea Melini was the first woman Charlie ever admitted he loved. Although claiming it was an accident at first, he doesn’t hide his true feelings for long and eventually expresses how he meant it. Eventually, however, Chelsea ended up leaving him for Alan’s lawyer.
Jennifer Taylor as Chelsea Melini | Now
While she may not have been written in the script to have won the heart of one of television’s most loved characters, Jennifer did continue to act following her appearance on Two and a Half Men. Following her stint on the series, she can be seen in shows such as Shameless, NCIS and Mom. She was also lucky in love outside of the show with the 45-year-old actress being married to songwriter Paul Taylor, with whom she shares two children with.
Emmanuelle Vaugier as Mia | Then
Charlie was a man who fought for what he wanted, and he certainly did that when it came to winning over dance teacher Mia. Claiming his nephew, Jake, enjoyed dancing, Mia eventually agreed to go on a date with Charlie, on the condition he gave up meat, smoking, and drinking. If that’s what it took, Charlie agreed, but of course, continued to do all three behind Mia’s back. Consequently, Mia leaves Charlie but comes back in a later episode to ask to use his sperm.
Emmanuelle Vaugier as Mia | Now
After playing Charlie’s love interest in Two and a Half Men, Vaugier continued to get hired for acting jobs and has had a successful career ever since. The Canadian-born actress has had television appearances in shows such as Lost Girl, One Tree Hill, Rogue and Mistresses, as well as, television movies such as Destruction Los Angeles and Washed Away. Now, aged 41, Emmanuelle Vaugier continues to pursue a career in acting and is currently filming a movie called Masks Don’t Lie.
Holland Taylor as Evelyn Harper | Then
The main woman in Charlie and Alan’s life was, of course, their mother. Although they had a strained relationship with their mother, played by Holland Taylor, she was a character on the show that the audience loved. She was known for neglecting her sons and getting involved with older men in hope to claim their assets when they passed away. Charlie and Alan would do all they could to avoid being in the same room with Evelyn, but it made for TV gold when they did.
Holland Taylor as Evelyn Harper | Now
Holland Taylor has become a face well recognized in Hollywood from her acting roles over the years and, even in her mid-seventies, Taylor continues to pursue a career in acting. While starring in shows such as The Orville and Hollywood Mom, she was recently cast in a big role for the show Mr. Mercedes where she plays Ida Silver. As for her personal life, she is not slowing down in the dating scene either, as she is in a relationship with Sarah Paulson, who is 30 years her junior.
Diora Baird as Wanda | Then
It’s not surprising that Diora Baird started out as a model for Guess. She also appeared in Playboy which gave her even more attention and fame. She’s absolutely stunning. Her first major role was in Wedding Crashers with owen Wilson. You may also remember her from The Texas Chainsaw Massacre: The Beginning. Since her time in the spotlight, things have changed a bit for the actress
Diora Baird as Wanda | Now
Since her time on Two And A Half Men, Diora Baird has starred in a few other roles. In 2014, she played a porn star in Beautiful Girl. She has also captured audiences with her recurring role in Cocked on Amazon. She has one child with her ex-husband, Jonathan Togo. Recently, she opened up about dating a female comedian Mav Viola.
Marin Hinkle as Judith Harper-Melnick | Then
Marin played Alan’s ex-wife, Judith Harper-Melnick, and she certainly did not make life easy for Alan. With the former couple sharing a son, Jake, they were often seen arguing about child support and alimony checks. There was further animosity since Judith liked to spend her alimony money on plastic surgery and luxurious purchases. She also married for the second time to Jake’s doctor, Herb Melnick, but this also ended in divorce when it was discovered that Herb was unfaithful to Judith with his secretary.
Marin Hinkle as Judith Harper-Melnick | Now
Following her role on Two and a Half Men, Hinkle has had a successful acting career and is currently starring on the CBS series Madam Secretary. Additionally, she has appeared as Dr. Miller in Speechless, and as Christine Lonas on Homeland. She has also starred in movies and just finished filming for Before/During/After. Hinkle has had more luck in her love life than she had in Two and a Half Men and is happily married to Randall Sommer.
Courtney Thorne-Smith as Lyndsey McElroy | Then
Lyndsey had many appearances on the show from season seven playing Alan’s love interest. It is hard to keep up with how many times the pair broke up and got back together, but it is certain to say that their relationship was very tumultuous. However, the pair had another connection since Alan’s son Jake was best friends with Lyndsey’s son, Eldridge. Lyndsey’s character was also known to be a heavy drinker, and this led to her lust for other men, including Walden, played by Ashton Kutcher.
Courtney Thorne-Smith as Lyndsey McElroy | Now
After playing Alan’s girlfriend, Lyndsey McElroy, on Two and a Half Men for a successful five years, Courtney Thorne-Smith decided to slow down her work in acting but has not given it up altogether. The actress has recently appeared in ABC’s new comedy series, Fresh Off The Boat, and has also offered her voice to the animated series, Robot Chicken. Meanwhile, Throne-Smith enjoys spending time with her son Jacob, and her second husband Roger Fishman when not acting,
Allison Janney as Beverly | Then
Alan met Beverly on a dating website, and she was soon invited to Charlie’s beach house. At first, Alan lies and claims the house is his in a way to impress his new friend. After Beverly opens up about her past marriages, Alan admits the truth that the house is his brother’s, but this does not seem to bother her. With her own demons to deal with, all things come to an end between the pair after Charlie walks into Alan’s room to find he has been tied up by Beverly.
Allison Janney as Beverly | Now
Allison Janney did not start her career on Two and a Half Men and is a very well known actress in Hollywood. She is probably best known for her role on The West Wing and has managed to keep a high profile in acting. Janney has appeared in award-winning films such as Juno, Hairspray, and The Girl on the Train, and is now a character on the CBS show, Mom, where she plays Anna Faris’ mother, a role that has earned her an Emmy Award.
Brooke Shields as Danielle Stewart | Then
Charlie initially introduces Alan to Danielle in a scheme to get him to move out of his house. Danielle was known to have been with many men in her past, and Charlie thought it was the time she settled for a lasting relationship. He thought his brother was the man for the job. However, after confiding in Charlie about her past, Charlie decides he wants to be with Danielle instead, and this results in the brothers fighting over her. In the end, Danielle leaves, and the Alan stays in the house.
Brooke Shields as Danielle Stewart | Now
Brooke Shields was cast as Danielle on Two and a Half Men already having a very successful acting repertoire. Having been working since she was a little girl, Shields is a highly recognized actress worldwide and, even in her early fifties, she continues to be recognized as the gorgeous model turned actress. With a long list of television shows and movies under her belt, she currently appears on Law & Order, and away from acting, she spends time with her husband Chris Henchy and their two children.
Jeri Ryan as Sherri | Then
Charlie met his match when he met Sherri. Known as quite the ladies man, Charlie found it too much that Sherri was similar to him in many ways. She was not one of the women that would fall for Charlie’s charm immediately and played hard to get, a trait Charlie was not a fan of, nor used to having to deal with. Eventually, this led to their downfall, but it did not stop her from going for Alan at one point. This too, however, did not last.
Jeri Ryan as Sherri | Now
The German-born actress continues to appear on television series following her stint on Two and a Half Men. She has appeared on shows such as Major Crimes, Body of Proof, and Helix, as well as Amazon Prime’s own show, Bosch. She was also cast as a Borg in the popular franchise Star Trek. Away from having her own successful acting career, she is happily married to her French chef husband, Christophe Eme, and the couple have two children together.
Kimberly Williams-Paisley as Gretchen Martin | Then
Gretchen Martin plays Larry’s sister who begins dating Alan. When meeting Gretchen, Alan decided to come up with an alter-ego and formed a new personality for himself. Claiming his son’s apartment is actually his, and that he doesn’t really live with his brother, was just one of the lies he formed alongside his new made-up identity. Gretchen, however, eventually finds out his lies and leaves Alan after admitting that she was previously married to a man who constantly lied to her.
Kimberly Williams-Paisley as Gretchen Martin | Now
Kimberly had been acting since a young age so Two and a Half Men was not her first acting experience. The actress was already well known for her role in the hit movie, Father of the Bride, and also appeared on According to Jim for eight years. Most recently, she has taken part in a festive film titled The Christmas Train, which is in post-production. As for her personal life, her hyphenated last name is from being married to country singer, Brad Paisley, and the couple have two children together.
Melanie Lynskey as Rose | Then
Anyone who was a fan of the show cannot forget Rose because Rose certainly made sure she was not to be forgotten after the one night she spent with Charlie. Having developed a deep obsession for Charlie, Rose stalked him regularly throughout the filming of Two and a Half Men. Eventually, Rose got what she had long desired with her and Charlie becoming engaged and running off to Paris together. However, Rose was never to have her happy ever after since Charlie died before they tied the knot.
Melanie Lynskey as Rose | Now
Before Melanie Lynskey became well known as Charlie’s stalker and a regular on Two and a Half Men, the New Zealand native had many appearances in other shows and films. Before being widely recognized as Rose, she appeared in Sweet Home Alabama and Heavenly Creatures, and is now filming for two new shows, one titled Castle Rock, and the other, Sunshine and Stephen King. Melanie Lynskey was also previously married to Jimmi Simpson but the pair eventually divorced in 2014.
Ming-Na Wen as Linda Harris | Then
Linda was another lady Charlie fell for, only to have to work very hard in order to win her over. After being introduced when Alan planned a double date involving his brother, Charlie thought Linda was very beautiful, but she just thought he was rude and was turned off by his personality. It turns out, however, that the two meet again when Linda is Charlie’s judge after he is charged with a DUI, and she decides to give him another chance. In true Charlie style, it doesn’t end well.
Ming-Na Wen as Linda Harris | Now
Ming-Na Wen was not new to Hollywood when she appeared in Two and a Half Men, and is actually the voice of the well-known Disney character, Mulan. Besides this notable role, Wen also starred on the hit television series, ER, as well as on shows such as Eureka and SGU Stargate Universe. Wen is still acting and can currently be seen in the sci-fi series Agents of S.H.I.E.L.D. Wen is married to Eric Michael Zee with whom she shares two children with.
Heather Locklear as Laura | Then
Charlie often chooses women who, in hindsight, he should have stayed clear from. Laura was one of those women since she was hired as Alan’s lawyer during his divorce from Judith. Having slept with Laura and promising always to be available to her whenever she wanted, Charlie eventually broke his oath and Laura took revenge. Unfortunately, the revenge was taken out on Alan when Laura decided to ruin the divorce settlement between himself and Judith. Consequently, Alan had to find a new lawyer.
Heather Locklear as Laura | Now
Heather Locklear made her appearance on Two and a Half Men as an already well-accomplished actress. Most famous for her roles on Melrose Place and Sin City, Locklear’s name had also made headlines for her very public divorce, as well as her health issues. Nevertheless, she managed to bounce back from both those obstacles and got her life back on track. She has since appeared on Franklin & Bash, and she now appears on Tyler Perry’s show, Too Close to Home.
Gail O’Grady as Mandi | Then
It was often hard for Charlie to resist any lady that came into his life, and it did not matter how he came to meet this person. This was even the case when Kandi’s mother came looking for her daughter and ended up at Charlie’s beach house. After welcoming his brother’s mother-in-law in, Charlie and Mandi spent the day together. It was argued that Kandi and Mandi looked very much alike, and were often mistaken for sisters, as opposed to mother and daughter.
Gail O’Grady as Mandi | Now
Before her stint on Two and a Half Men, Gail O’Grady appeared on the television show, American Dreams. After playing Mandi, O’Grady appeared on Ms. Fields and Revenge, continuing a successful acting career. Things cannot be said for her personal life, however, with O’Grady having had her fair share of husbands in the past. In fact, the actress has been married six times, with her last marriage to John Stamatakis ending in 2008. Nevertheless, she remains hopeful and is currently dating Chris Beyers.
Paula Marshall as Paula | Then
Paula was like a bright light who came into Alan’s life when they met in a nightclub. The pair hit it off instantly, but in true Two and a Half Men style, no relationship is smooth sailing. Well, Paula reveals to Alan she used to be a man called Paul and was married to Rachel. Paula admits she wants to be in an open relationship, so Alan starts dating Rachel. Eventually, however, the two ladies decide to give it another go and leave Alan.
Paula Marshall as Paula | Now
Paula Marshall has appeared in many television shows other than Two and a Half Men and some of these include, House, Law and Order, Murder in the First, Switched at Birth, and The Mentalist. Most recently, Marshall appeared in the movie, We Love You, Sally Carmichael! She is also married to fellow actor, Danny Nucci, who had his breakthrough acting role playing Fabrizio in the award-winning and highly acclaimed film, Titanic. Together, the married couple has a daughter named Maya.
Missi Pyle as Miss Pasternak | Then
As mentioned before, Charlie charmed every woman that came his way, and no woman was off limits, not even Jake’s elementary school teacher. Meeting another lady through Jake worked to his advantage this time around, with Miss Pasternak giving Jake good grades since dating Charlie. Upon discovering that she has a mental problem, Charlie is quick to dump her, but she appears seasons later to inform Charlie she is no longer allowed to be a teacher and is working as a dancer and living in a motel.
Missi Pyle as Miss Pasternak | Now
The Texas-born actress has continued her acting career following her appearance on Two and a Half Men. Missi Pyle has appeared on Inside Amy Schumer and Sing it, and is also set to appear on the movie release of Jumanji. She has also appeared in The Artist and Gone Girl, with other projects in the pipeline to be released. As for her personal life, Pyle has been married twice and is not looking to get married again anytime soon, so is currently taking a break from marriage.
Kimberly Quinn as Donna | Then
When Charlie met Linda on a double date with Alan, this was the same time Donna and Alan were introduced. Fortunately, this date went well for them and continued to do so till Alan decided he was bored of her and wanted to end it. Turning to Charlie for help on how to do so, he is advised to let her down gently. Choosing to follow Charlie’s advice does not work in his favor since Donna becomes hysterical over the news that Alan is breaking up with her.
Kimberly Quinn as Donna | Now
Following her appearance on Two and a Half Men, Quinn can currently be seen on multiple television shows including Twisted and Netflix’s own series, Gypsy. In her personal life, Quinn is married to producer Theodore Melfi, who is well-known for his work on movies such as St. Vincent and Hidden Figures. It is no coincidence then that Quinn got an acting role in St. Vincent by playing the role of Nurse Ana. It must be good to have a husband in such high places.
Tammy Lauren as Shannon | Then
Alan meets Shannon at Judith’s second marriage to Herb and later finds out from Charlie that Shannon was once engaged to Herb. Still both hung up on their previous relationships, the two attempt to make their former lovers jealous by pretending to get intimate at the wedding. Shannon does not hold back and even screams out Alan’s name for all the wedding guests to stop in their tracks and hear. This relationship, however, was not to last long and neither win back the hearts of their exes.
Tammy Lauren as Shannon | Now
During her appearance on Two and a Half Men, Tammy Lauren was a regular on The Young and the Restless and continued to play detective Maggie Sullivan on the soap opera after her romance with Alan ended. Otherwise, Lauren has not had much success in acting, having only appeared on a single episode of the show Criminal Minds in 2014. It is unknown if this is a personal choice, but it can be assumed that she has chosen to focus her attention on her marriage to fellow actor, Guri Weinberg.
Justine Eyre as Gabrielle | Then
Things were not always easy for the brother’s living in the same house with each other, and their relationship was often met with some obstacles. When Charlie started dating Gabrielle, Alan found out that Charlie had stolen a girlfriend from him in high school and decided to take revenge by stealing Gabrielle. Successful in doing so, he then decides to end it when he finds the situation “uncomfortable.” After his break-up, he goes home to find Charlie with his high school girlfriend, Charity, and Alan decides they are now even.
Justine Eyre as Gabrielle | Now
While Justine Eyre has not become a big household name like the other actresses who appeared on Two and a Half Men, she has had appearances on hit television series such as Mad Men, The Secret Life of the American Teenager, and CSI: Miami. Additionally, she has not acted since 2016, but that is not to say that she has given up on acting or will no longer be cast in future roles. Eyre is married to screenwriter, John Allen Nelson.
Maggie Lawson as Ms. McMartin | Then
Even after Charlie left the show, no woman was off limits for the remaining characters. The same went for the social worker, Ms. McMartin, who was assigned to Walden and Alan when they decided to adopt a child. The two men were given a child named Louis, but the adoption does not last long when McMartin discovers the pair are deceitful. Fortunately, McMartin changes her mind once again and begins dating Alan. Nevertheless, she then leaves him to begin a relationship with Walden.
Maggie Lawson as Ms. McMartin | Now
Similar to the other women who have been successful before and following Two and a Half Men, Maggie had the same luck. Lawson appeared in shows such as Psych, Angel From Hell, and The Great Outdoors. Currently, Maggie is set to play Juliet O’Hara in the movie version of Psych which is set for release at the end of 2017. Away from acting, Maggie is married to fellow actor Ben Koldyke who is best known for his role in the NBC series, Mr. Robinson.
Kelly Stables as Melissa | Then
Melissa was another woman who got her hands on both Charlie and Alan. Cast as Alan’s secretary, Melissa began dating Charlie but then started a relationship with Alan. Once again, however, Alan is discovered to have lied about his life, and this time it was about renting a home. Even while Alan is living with Lyndsey, the pair continues to have an on/off relationship, with Melissa asking for health insurance and a raise, until Alan eventually decides to end their relationship via text.
Kelly Stables as Melissa | Now
While her appearance on Two and a Half Men came to an end when Alan decided to move on, Kelly has remained very much on the Hollywood scene and continued to pursue her acting career. The actress was the voice in the animated show, W.I.T.C.H, and has appeared in films such as Horrible Bosses 2, as well as on television shows including Superstore and Malibu Dan the Family Man. She has been married to Kurt Patino since 2005, and the married couple has one song together.
Denise Richards as Lisa | Then
Before there was Alan, there was Lisa, who was Charlie’s girlfriend and lived in his home. Known for his struggle to commit, the issue arose when he was with Lisa, and he decided to break up with her. When Lisa tells him she wants to get married, Charlie lies by saying he has become a family man. This obviously worked since Lisa divorced her husband and gave Charlie another chance. The facade did not last long and his commitment phobia led to their downfall once more.
Denise Richards as Lisa | Now
The difference between this leading lady winning the heart of Charlie and all the others? Well, Denise was actually married to Charlie Sheen in real life. Denise Richards and Charlie Sheen were married from 2002 until 2006, and had two daughters, Sam and Lola, during that time. Although they ended on good terms originally, their divorce became a very public and bitter affair making many media headlines. Meanwhile, Richards is still a working actress and has adopted another daughter, named Eloise, since her divorce from Sheen.
Conchata Ferrell as Berta | Then
Probably the only woman that had no romantic link with Charlie when they appeared on Two and a Half Men was Berta, the maid who worked in Charlie’s home. Although Charlie did not get along with Berta, she was a series regular and offered a lot of comedy for her work in the beach house. Spending most of her time making fun of Alan and Charlie, she was a real fan favorite and was kept on the show after Charlie was killed off to become Walden’s housekeeper.
Conchata Ferrell as Berta | Now
Becoming widely known as Berta, Conchata will most likely always be most recognized for her role in Two and a Half Men. Conchata has had several acting jobs since the ending of the series and has appeared in the fantasy film Krampus. Currently, Ferrell has a reoccurring role as Shirley on the comedy show, The Ranch, where she stars alongside her former co-star Ashton Kutcher once again. She is married to fellow actor Arnie Anderson, and together they have a daughter.
Jenny McCarthy as Courtney Leopold | Then
Soon to be his step-sister was not something that would stop Charlie from dating Courtney, whose father was set to marry his mother. Alan sees early warnings that Courtney has sociopathic tendencies and warns his brother. Even after she convinces Charlie to buy her a Ferrari, as well as give her $50,000, that still does not stop Charlie from dating her. It all comes to an end when he finds out that her real name is Sylvia and she and her “father” are con-artists.
Jenny McCarthy as Courtney Leopold | Now
McCarthy had long made a name for herself as an actress before Two and a Half Men. While she had her own show in the 1990’s, she was also a Playboy bunny and had a very public romance with fellow actor Jim Carrey. From a previous relationship, she has one son who is autistic, and she advocates awareness for the condition. She also makes her views very public on her thoughts about being against giving disease preventing vaccinations to children.
Teri Hatcher as Liz | Then
While Judith had enough trouble dealing with Alan, and Charlie for that matter, things only got worse when her sister paid a visit to Jake’s birthday party. Although Charlie and Liz got together at Alan and Judith’s wedding, which Charlie, of course, does not remember, Liz makes a move on Alan at the party and consequently upsets Judith. However, we then find out that before Alan and Judith started dating, he had, in fact, tried to date Liz. Although they eventually end up in a room together, nothing actually happened.
Teri Hatcher as Liz | Now
Shortly after her role in Two and a Half Men, Teri Hatcher became a household name as Susan Mayers on the hit series Desperate Housewives. After starring in this role for eight years, Hatcher made television appearances on Supergirl and The Odd Couple. Hatcher, much like her character of Susan, has not been so lucky in love, having gone through two divorces and still on the hunt for her perfect love. She does have one daughter with her first husband.
Jaime Pressly as Tammy | Then
When Jake introduces his new girlfriend to his father, it is unsurprising that Alan was not best pleased with his son’s decision. His new girlfriend, Tammy, is a mother of three and owns her own tattoo parlor called Tammy’s Tatties while having her own tattoos to show off. However, it is not because of Alan’s disproval that the pair ends their relationship, but rather because Tammy finds out that the teen was once in a relationship with her own daughter, Ashley.
Jaime Pressly as Tammy | Now
Jamie Pressly is another Two and a Half Men alum who was already well known on the Hollywood scene. She has previously had roles in Not Another Teen Movie and I Love You, Man. Most recently, Jamie has decided to focus her attention on television and appeared on I Hate My Teenage Daughter and is currently a prominent feature on the CBS comedy, Mom. She was previously married to Simran Singh and has three daughters; however, the pair ended their relationship in 2011.
April Bowlby as Kandi | Then
Kandi was well known on the show for her ditzy personality. Having found her ways into Charlie’s arms originally, she also finds her way to those of Alan’s, and Alan’s former lawyer. Eventually, however, she ends up marrying Alan in a Vegas wedding and moves in with him. Just like Alan’s bad luck with love in the past, this proves to be no different after Kandi lands a part in the show, Stiffs, and chooses to break up with Alan.
April Bowlby as Kandi | Now
Just like many of the other leading ladies who appeared on Two and a Half Men, April continued to make a name for herself as a successful actress. She has appeared on other TV hit shows such as The Big Bang Theory, How I Met Your Mother, and Drop Dead Diva. Currently, Bowlby is filming a movie titled Love Me or Else, and is involved in a project called Reunion. She has also made news in her personal life for dating the well-known singer, Josh Groban.
Judy Greer as Bridget Schmidt | Then
When Ashton Kutcher was first introduced to the show, playing the role of Walden, we learned that he was divorced from Bridget. Having been so in love with Bridget and struggling to get past their break-up, Walden even goes as far as to try to take his own life when she refuses to take him back after believing he is too immature. This all changes when he begins dating Zoey and Bridget finds out, resulting in her paying a visit to Walden’s home and begging for him to take her back.
Judy Greer as Bridget Schmidt | Now
Judy Greer has made quite a name for herself, and not just with acting. She went behind the scenes by taking the role of casting director for the film version of Entourage and also lent her voice to animated shows such as StoryBots and Archer. Nevertheless, Greer continued to showcase her talents in front of the camera following her role as Walden’s ex-wife on Two and a Half Men and was recently cast in the remake of the hit movie, Halloween.
Sophie Winkleman as Zoey Hyde-Tottingham-Pierce | Then
The girl who eventually allowed Walden to get over his ex was Zoey. Besides having an incredibly long last name, Zoey was the good-looking British siren who won Walden’s heart, only to break it two years later when the single-mother declined his proposal. Walden later discovered that Zoey had been dating another man during their relationship, and as revenge, he gifts Zoey’s daughter a vicious dog for her birthday, a gift his former lover surely would have not been impressed by.
Sophie Winkleman as Zoey Hyde-Tottingham-Pierce | Now
This British beauty is in fact married to English royalty after tying the knot with Lord Frederick Windsor, the distant cousin of Queen Elizabeth. Although Winkleman is nobility through marriage, she has continued to appear on camera for her acting skills since her two-year stint on Two and a Half Men. She is currently filming a new show titled, Thrust, alongside Donald Sutherland and Hilary Swank. She has also previously voiced a character on the show Milo Murphy’s Law.
Krista Allen as Olivia Pearson | Then
Charlie comes face to face with a former flame when he goes to his mother’s house. At the time, his mother Evelyn had a boyfriend around at her house and had brought his daughter along, Olivia, who just happened to be one of Charlie’s past girlfriends. Things went downhill when it was discovered that the two were once involved with one another, and a few drinks were thrown in people’s faces. Things did not end well for Evelyn either since her boyfriend dumps her for a younger woman.
Krista Allen as Olivia Pearson | Now
Kirsta Allen appeared on Two and a Half Men having already secured a successful acting career since the 1990s. Her breakthrough role was on the popular soap opera, Days of Our Lives, which has been running for 53 seasons and made her a household name. She also appeared in films alongside her television appearances such as The Final Destination and Anger Management. Currently, she is set to star in upcoming films titled Best Mom, and a comedy film called Eleven Eleven.
Kristin Dattilo as Cindy | Then
Cindy was one of the very few Charlie failed at getting into bed with him. While he was not having much luck, his nephew, Jake, began to have a crush on Cindy and decided to draw some of her assets for a school art project. Meanwhile, Jake’s mother, Judith, meets Cindy and the two bond instantly over their tumultuous relationships with their fathers. After spending so much time together after their instant bond, Alan starts to speculate that the two are even dating.
Kristin Dattilo as Cindy | Now
Kristen is best known for playing Yola Gaylen on The Chris Isaak Show from 2001 to 2004 but has also had appearances on hit television shows. These include CSI, Dexter, Beverly Hills, 90210, Friends, Grounded for Life, and Veronica Mars. She is married to Jason Keller, and the couple has two daughters together, Eve and Quinn. She previously took time away from acting to focus on her children, and while pregnant with her second child, she discovered writing which she went on to pursue.