On September 22, 2003, the first episode of the television sitcom Two and a Half Men premiered starring Charlie Sheen (Charlie Harper), Jon Cryer (Alan Harper), and Angus T. Jones (Jake Harper). The series followed the two and a half men as they Sheen’s character lives a hedonistic life. That lifestyle led to many dates with beautiful women as the series progressed.
After Sheen’s departure from the show, Ashton Kutcher (Walden Schmidt) filled the void playing a recently divorced billionaire. Sheen leaving didn’t stop the flow of estrogen on the show by any means. Since ending in 2015, what are those lovely ladies up to these days?
Kelly Stables – “Melissa”

A woman who had a recurring role on the show was Melissa, played by Kelly Stables. She was Alan Harper’s receptionist, who Charlie tried to get to fall for him. Eventually, she started a relationship with Alan. The relationship ends with Alan breaking up with her over a text.
Today, Stables is a recurring character on the TV show Superstore. She’s landed plenty of roles throughout her acting career as well. Stables has a husband, Kurt Patino, and a son as well.
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Jennifer Taylor – “Chelsea”

At the beginning of Charlie’s relationship with Jennifer Taylor’s character Chelsea, he strictly saw her as a one-night stand. Over time, that changed as Charlie began to grow feelings for her. As a result, Chelsea had the pleasure of becoming the first woman Charlie ever professed his love to. She ends up leaving him for Alan’s lawyer.
Taylor is now married to Paul Taylor. One of her most recent TV appearances comes from the hit series Shameless. Taylor also has two shows still in post-production.
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Courtney Thorne-Smith – “Lyndsey McElroy”

Courtney Thorne-Smith played a slightly masculine character by the name of Lyndsey McElroy. She enjoyed drinking and was Alan’s on-and-off romantic partner. She had a serious drinking problem as well. She was very caring, but also a super flirt.
Smith played this role for five years and once it ended, she took a break from the Hollywood lifestyle. She did do a voice a character on the adult cartoon show Robot Chicken before appearing on Fresh Off The Boat.
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Emmanuelle Vaugier – “Mia”

Emmanuelle Vaugier’s character Mia was a dance instructor who didn’t give Charlie the time of day. It wasn’t until she found out that Charlie had a nephew who was also interested in dancing that she decided to give Charlie a chance. The two almost get married but that fails when Charlie tells her his brother won’t move out.
The Canadian actress, model, and singer continued to thrive after appearing in this series. She locked down various roles and continues to make her career blossom.
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Megan Fox – “Prudence”

During season one, Megan Fox plays a granddaughter who can’t be left alone at home. She ends up getting brought to Charlie’s beach house, where everyone was left stunned by her figure and looks, even Jake!
Fox might be one of the biggest stars on this list. A cameo in this show probably ranks towards the bottom of her career accomplishments. After appearing in huge blockbuster films like Ninja Turtles and Transformers, Fox has been relatively missing from the acting scene.
Up next, someone who appeared to be innocent but deep down had another side…
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April Bowlby – “Kandi”

April Bowlby’s character portrayal on the series is that of a young, sweet, and somewhat innocent charmer. Beneath the surface, she enjoyed sleeping with older men, including Charlie. She somehow ends up getting Charlie, Alan, and Alan’s former lawyer too! In the end, she chooses to marry Alan but dumps him after accepting a new job.
These days, you can still catch Bowlby acting. She’s appeared in shows like The Big Bang Theory, How I Met Your Mother, and Drop Dead Diva. The actress also gained some extra notoriety over her relationship with Josh Groban.
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Holland Taylor – “Evelyn Harper

Holland Taylor played Evelyn Harper, Charlie and Alan’s neglectful mother. Many argue that she could easily be the funniest character on the show. Both of her sons tried their hardest to avoid her as much as possible. She would also get with older men for their assets and money.
Taylor still powers through as a recognizable and respected figure in Hollywood. Her talent has allowed her to land jobs in the industry and we love to see her do what she does best
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Marin Hinkle – “Judith Harper-Melnick

Marin Hinkle played Alan’s first wife, Judith Harper-Melnick. She was also the biological mother of Jake Harper. The relationship she had with Alan was so bad that she admitted to only being happy while pregnant with Jake! The two eventually divorce and she goes on to marry Jake’s pediatrician.
Today, Hinkle is still sharpening her acting chops. You might have noticed her in the CBS series, Madam Secretary. She also was in Homeland and Speechless. Hinkle has a successful marriage with Randall Sommer.
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Allison Janney – “Beverly”

Alan met Allison Janney’s character Beverly via a dating site. He really wanted to impress her so he told Beverly that the beach house was all his. Upon feeling bad about her recent divorce issues, he comes clean and reveals that the house is Charlie’s.
How could you not recognize Allison Janney? She’s been in hit movies like Hairspray and Juno. The work she’s done in acting has earned her seven Primetime Emmy Awards, a Golden Globe, and Academy Award, and much more!
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Brooke Shields – “Danielle Stewart”

Brooke Shields played a girl with a partying past, but that didn’t stop Charlie from setting her up with Alan. Alan tells Danielle Stewart that he’s going to change for her, something no other guy has told her. After Danielle tells Charlie, “I’ve slept with a lot of guys and even a few women and even with couples,” he all of a sudden wants her and fights Alan, causing her to leave.
Clearly, Shields was already a prominent actress before she appeared on this show. She grabbed her first lead role at the age of 12. You might have caught her on Law & Order: Special Victims Unit.
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Jeri Ryan – “Sherri”

Sherri was a type of girl Charlie had never encountered before. She was very skilled at the art of playing hard to get and would constantly lead Charlie to have relations with her. He thought he was the one getting used so he plotted revenge and that’s what led to their downfall.
Jeri Ryan might be best known for her role on Star Trek: Voyager which helped her earn four Saturn Awards. Her latest work is a project called The Relic.
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Kimberly Williams-Paisley – “Gretchen Martin”

After one of Alan’s ex-girlfriends begins dating another guy, he decided it would be a bright idea to date that guy’s sister, Gretchen Martin. She becomes a recurring character as she keeps up a relationship with Alan’s alter ego, Jeff Strongman. She eventually calls him out on all his lies and dumps Alan.
You might recognize Kimberly Williams-Paisley from Nashville or According to Jim. She appeared in the later episodes of Two and a Half Men, so after the show, she slowed down acting a bit. She’s probably too busy focused on her marriage with Brad Paisley.
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Judy Greer – “Bridget Schmidt”

As Ashton Kutcher’s character gets into the swing of things, the audience soon finds out about his past aka his divorce with Bridget Schmidt. He loved her so much that he was willing to take his life for her. After she discovers that he’s dating someone else, she tries to get him back but it was too late.
Judy Greer is a well-established director, actress, model, and author. Greer has also done great work as a voiceover actress for animated shows like Archer and StoryBots.
Did you know that there was a royal involved in the show?
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Melanie Lynskey – “Rose”

Melanie Lynskey’s character Rose ended up becoming a regular on the show and one of the audience’s favorites. Charlie thought it was only a one-night stand, but it escalated to an obsession. Charlie eventually falls for her and they decide to get married, but Charlie’s character passes away before they make it official.
Hailing from New Zealand, Lynskey plays roles where she is soft-spoken, quirky, and flawed. After this show, she went on to win multiple awards in other acting opportunities.
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Heather Locklear – “Laura”

While Alan was going through a rough patch trying to get his divorce settled, something happened. In true Charlie fashion, he messed things up by sleeping with Alan’s attorney, Laura. After Charlie broke his promise being available to her whenever she wanted, she sabotaged Alan’s divorce proceedings.
Even before appearing on the show, Heather Locklear was a well-established name. She’s fought through a publicized divorce and a few health issues. Locklear is ready for more roles, as she’s appeared on Fresh Off the Boat in 2017.
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Gail O’Grady – “Mandi”

Remember Kandi from earlier? Well, this is her mother, Mandi, played by the great Gail O’Grady. She first appears when she comes looking for Kandi, but ends up getting intimate with Charlie for the whole day! Kandi and Mandi looked so much alike, the neighbors mistook them for twins.
O’Grady is a producer and an actress. She’s booked tons of lead roles for television movies that ultimately led to her gaining three Primetime Emmy Award nominations. In her personal life, she’s gone through six marriages, all of which have not worked out.
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Missi Pyle – “Miss Pasternak”

“I don’t think limits,” a famous quote from the fastest man in the world, Usain Bolt. That must have been Charlie’s inspiration because it didn’t matter who the woman was, he would pursue her. That included Miss Pasternak, Jake’s teacher. Charlie starts dating her and she begins to give Jake good grades without him earning it. Then, Charlie found out she was mentally ill so he dumped her.
In the real world, Missi Pyle is quite accomplished. She’s been in Charlie and the Chocolate Factory, 50 First Dates, and more blockbusters! She keeps busy by working on multiple projects.
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Paget Brewster – “Jamie Eckleberry”

Flickr/ The Celebs Fact
In season one, we learn of an acquaintance from Charlie and Alan’s past named Jamie Eckleberry. They called her “Ugly Eckleberry Hound” when they were kids but as an adult, Jamie lost a lot of weight and became a bombshell. Charlie and Alan both try to hit on her and she is able to get revenge on them both by rejecting them.
Jamie is played by Paget Brewster, who is best known as Special Agent Emily Prentiss on Criminal Minds. These days, you can catch her as the voice of Della Duck on Duck Tales.
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Miley Cyrus – “Missi”

Outside of Alan’s and Charlie’s plethora of flings and girlfriends, what fans really liked to see was any of Jake’s love interests. After all, the kid has been on the show since he was, well, a kid and it’s always interesting to see how they grow up. One of his first girlfriends was Missi, though we don’t meet this character until season ten.
Missi first appears in the episode “You Do Know What The Lollipop Is For,” when Jake comes home from the Army. After Jake goes AWOL, Missi feels uncomfortable about his feelings for her and she convinces him to return to the Army.
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Justine Eyre – “Gabrielle”

Canadian actress Justine Eyre appears in season five as Gabrielle. She starts out as Charlie’s girlfriend but manages to get whisked away by Alan, who steals Gabrielle as revenge for Charlie previously stealing one of his girlfriends in high school. After Alan feels bad, Charlie encourages him to keep dating her only for Alan to discover her “bedroom style.”
Prior to her guest spot on Two and a Half Men, Eyre was known for her role as Karen on Ocean Ave. Most recently, she appeared on the Hallmark Channel’s Winter Castle.
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