The real-life relationships of the Two and a Half Men cast

Over the years we have fallen in love with some of the best characters on TV. From laughing along with their joy to shedding a tear or two during those oh-so emotional moments, sitcoms have given us some of the most memorable scenes to date. So it may be no surprise that we so quickly fall in love with the starring characters of the show. When it comes to the stars of Two and a Half Men, everyone brought something to the show to make it their own.

Whether it was the perfectly times comebacks or the loveable personality, the show would be nothing without the stars of the series. So just what happens when the cameras on the Two and a Half Men set stop rolling? Is Charlie Harper really the womanizer he is made out to be? Does Alan Harper ever find someone to love? Please tell us Herb Melnick is able to find someone to call his own?!

Back in 2003, our screens were graced with a brand new Chuck Lorre creation. Two and a Half Men. The sitcom was like no other that had ever appeared on our screens as we got to watch brothers Charlie Harper (Charlie Sheen) and Alan Harper (Jon Cryer) raise Alan’s son Jake Harper (Angus T. Jones) together. Although the show focused on the three main characters, there were plenty of other personalities that became entwined in the storyline over the seasons. It wasn’t just the drama on the show that kept us hooked all those years, either. No, the drama that came from outside the filming studios had us on the edge of our seats. With two of the leading cast members leaving the show, how would TAAHM go on without them?

The series officially came to an end three years ago, but that doesn’t mean these actors’ lives have slowed down in Hollywood. Over the twelve years of the show’s run, we got to see various actors and actresses grace our screens. With so many relationships on the show, did the actors learn anything about how to – or how not to – date? Perhaps some of the stars hit it off on the set and have been happily married ever since? Maybe they watched the unwindings of the on-screen relationships and thought better than heading into the world of love? Sadly, Hollywood isn’t always a place for fairy tales. Sometimes these stars get caught up in the whirlwind of the moment, and often these choices can have disastrous effects…

Sarah Paulson and Holland Taylor (dating 2015 – present)

During the show, Holland brought Evelyn Harper to life. Evelyn was the often self-centered and vain mother of Charlie and Alan. Although her TV character was often seen dating and marrying (or trying to marry) various wealthy men, in real-life Holland has settled down for the long run with Sarah Paulson. The couple publicly announced their relationship in 2015. The fellow actress shot to fame after landing roles in thriller series, American Horror Story. There may be a 30-year age gap between the two, but they aren’t letting anything hold them back. In fact, they have both spoken about how they are the best thing to happen to each other.

Mila Kunis and Ashton Kutcher (married 2015 – present)

After Charlie Sheen’s dramatic exit from the show, Ashton Kutcher took over as the leading role by playing adorable and heartbroken millionaire and tech genius Walden Schmidt. Shortly after Ashton joined the show, Mila Kunis made a guest appearance. Of course, it wasn’t the first time the pair had teamed up on-screen. The couple had already spent eight years working together on the sitcom, That ‘70s Show. Nearly two decades after first meeting, in 2015, the duo finally tied the knot. The two have gone on to become one of the most loved couples in Hollywood. Mila and Ashton are now also parents as they have both a daughter and a son.

Randall Sommer and Marin Hinkle (married 1998- present)

Judith Harper-Melnick: Jake’s mother and ex-wife to Alan. On the show, the character ran through a number of marriages that all ended in disaster. While Marin may have played the unlucky in love character, in reality, her life is quite the opposite. Marin met director Randall Sommer back at the beginning of the ‘90s, and the pair were dating for six years before finally walking down the aisle in 1998. To date, the couple appear as though they are stronger than ever.

Roger Fishman and Courtney Thorne-Smith (married 2007 – present)

TAAHM has seen many women come and go as they date various members of the Harper family, with Lyndsey being no exception. Over the series, she was in an on/off relationship with Alan until they finally call it quits. While Courtney struggled to find love on the show, in real-life she has been nothing but successful. The actress met Roger Fishman, the president of the social media video developing company, Zizo Group, and the pair said “I do” 2007. One year later the couple welcomed Jacob, their first son.

Patricia McDonald and Ryan Stiles (married 1988 – present)

Ryan has been performing comedy since before comedy was a thing after he landed a spot on the improv series, Whose Line Is It, Anyway? It was his life in stand-up that meant that Ryan was in the right place at the right time. While performing at the Punchlines Comedy Club, there was one very special lady in the audience: Patricia. The waitress was working at the club when she locked eyes with the comedian, and the rest is history. The pair have since gone on to have three children together.

David Cross and Amber Tamblyn (married 2012 – present)

Jenny Harper made waves on the show when she appeared as the illegitimate daughter of Charlie. It isn’t just the on show that Amber has caused a stir, either. Back in 2012, the actress walked down the aisle with fellow actor, David Cross. David is best recognized as Tobias Fünke in the sitcom Arrested Development. However, it was the 20 year age gap that had everyone talking. Regardless of the gossip, the pair have gone on to settle into married life and even welcomed their first daughter in February 2017.

Josh Groban and April Bowlby (2009 – 2010)

On TAAHM, April Bowlby guest starred as the ditzy Kandi for seventeen episodes. Chuck Lorre must’ve enjoyed her acting style as the actress has recently made a guest appearance on his other sitcom, the Big Bang Theory. Even though April is used to being in the limelight, she tried to keep her private life just that. However, that didn’t stop rumors from circling that April was dating singer Josh Groban for a year. Could the stories have been true?

Chuck Lorre and Emmanuelle Vaugier (dated 2010 – 2012)

The co-creator of the sitcom couldn’t stay away from Emmanuelle when she was cast to play Mia for twelve episodes. For two years the pair were in a happy relationship until Emmanuelle discovered Chuck’s hidden secret. He has been having an affair with another woman while the actress had been working away. The news was too much, and the pair ended up calling the relationship off. For Chuck, his career has only continued to grow as he has created hit sitcoms such as Mom, and The Big Bang Theory.

Ashley Vachon and D.B. Sweeney (married 2000 – present)

On the show, D.B. played Lyndsey’s ex-fiancé who went on to become a close friend with Alan. It wasn’t just TAAHM that saw the actor drop to one knee. No, in fact back in 2000 D.B. wed author Ashley Vachon. The writer is best known for her romance novels Billionaire’s Romance and Pregnancy Romance. The pair quickly welcomed two children, Cade and Cody. Sadly for D.B. at the moment, it looks as though his children are more interested in sports that they are following in his acting footsteps.

Lord Frederick Windsor and Sophie Winkleman (married 2009 – present)

For 18 episodes we got to see Walden and Zoey’s relationship blossoming, unraveling, and ultimately end. While on-screen relationships may not be this actresses forte, in the real world Sophie has landed herself a royal catch. Lord Frederick Windsor is the son of Prince Michael of Kent who just so happens to be the Queen’s first cousin. We’ve got it. This means Sophie is now officially a Lady since marrying into the family back in 2009. The pair share one daughter, Maud Elizabeth Daphne Marine Windsor.

Ginny Gardner and Graham Patrick Martin (dating 2014 – present)

It wasn’t just playing Eldridge on TAAHM that saw actor Graham Patrick Martin shoot to fame. Over the years the actor has become famous for his character Rusty Beck in the police drama, Major Crimes. For the last few years, Graham has been dating fellow actress Ginny Gardner who was thrust into the limelight after landing a part in the sitcom, The Goldbergs. The pair both continue to act, with Ginny even landing some movie roles in recent years.

Dean E. Johnsen and Judy Greer (married 2011 – present)

This actress has won the hearts of the nation for her varied acting roles. Although on TAAHM the actress played Bridget, Walden’s ex-wife, Judy is best known for her role as Cornelia in the sci-fi Planet of the Apes franchise. It was her roles in the movies that saw Judy plan a particularly unique wedding day. She met TV producer Dean Johnson who just so happened to be a major fan of the films, too. So it only seemed fitting that their wedding have a Planet of the Apes theme!

Sarah Trigger and Jon Cryer (married 1999 – 2004)

Alan: the loveable other half of the Harper brothers on TAAHM. On the show, the character finds himself in various troublesome relationships before finally settling down with Gretchen. In reality, the actor walked down the aisle in 1999 with Sarah Trigger, a retired actress herself. Sadly, the marriage wasn’t to last, and the couple spent months battling out their divorce in the courtroom just five years later. Together they have one son, aptly named Charlie, but Sarah’s recent request of $88 a month for child support was overruled by the judge.

Paul Taylor and Jennifer Taylor (married 1997 – present)

This actress played Chelsea, another one of Charlie Harper’s ex-fiancées, during her time on TAAHM. While her character’s love life may have been unkind, in reality, Jennifer has just passed her China wedding anniversary with husband, Paul Taylor, after twenty years of marriage. Jennifer tied the knot with her songwriter husband back when she was only 25 years old, but has never looked back. In fact, their marriage makes the pair one of the strongest couples in Hollywood! Together, Jennifer and Paul have gone on to share two children together.

Kurt Patino and Kelly Stables (married 2005 – present)

On the show, Melissa was the sweet ex-girlfriend and receptionist of Alan Harper. In real-life, it appears as though Kelly Stables is just as lovable. The actress walked down the aisle in 2005 with her producing and screenwriting boyfriend, Kurt Patino. Over the years, Kurt has written a number of his own short films, including Soul Fire Rising and Cup O’ Joe, as well as running Patino Management Company, a talent agency in Burbank. The pair have gone on to share two sons, 5-year old Kendrick and two-year old Kellen.

Donnie Wahlberg and Jenny McCarthy (married 2014 – present)

This star appeared on TAAHM when she was cast to play Courtney Leopold, the con-artist who manages to manipulate Charlie. However, in 2014 there was no manipulation needed as Jenny walked down the aisle with Donnie Wahlberg. The name may sound familiar, and you’d be right. Donnie is the older brother of Hollywood actor, Mark Wahlberg. Although he has since gone into acting himself, Donnie first made his claim to fame after helping to found the hit ‘80s boy band, New Kids on the Block.

Amanda Crew and Clark Duke (2008)

Before appearing on the show, Clark had made his claim in Hollywood after landing roles in the comedy movie Hot Tub Time Machine, as well as the comedy-drama show, Greek. However, it was playing the role of Walden’s roommate, Barry, in 2014 that welcomed Clark to the TAAHM family. Back in 2008, Clark had just released a movie where he starred alongside Amanda Crew when the rumors began to spread. Their on-screen chemistry had everyone in Hollywood talking, but the pair never confirmed they were in a relationship.

Ben Koldyke and Maggie Lawson (married 2015 – present)

Ms. McMartin was the social worker assigned to Alan and Walden when they are desperate to adopt a child into their family during the final season of the show. Before becoming part of the cast, Maggie had already become famous for her role as Detective Jules O’Hara in the detective comedy-drama, Psych. The actress has appeared in a vast number of hit shows and movies over the years, but it was working on the 2013 sitcom Back in the Game that saw the star meet beau, Ben Koldyke.

Noah Engh and Rachel Cannon (married 2013 – present)

Although Rachel only appeared in one episode of TAAHM, the actress has enjoyed a thriving career so far. On the show, Rachel brought Chloe, Charlie’s girlfriend, to life. However, things weren’t all simple as Enrique Iglesias aka Fernando also had his eye on Chloe. In reality, this actress has her eyes firmly on her man, Noah, as the pair tied the knot in 2013. The couple mainly keep away from the media but do send out updates on Instagram of their family life with their son, August.

Demi Moore and Ashton Kutcher (married 2005 – 2013)

Before the days of ‘Milton’, there was another Hollywood power couple dominating the red carpet: ‘Ashmi’. Ashton and Demi walked down the aisle back in 2005, and they looked as though they were in for a smooth ride. Unfortunately, it wasn’t to last. Everything came crashing down after eight years as Demi learned of Ashton’s affair with 22-year-old Sara Leal. The divorce lasted over a year, and Sara reported how the romance ruined her life – it seems as though it wasn’t a good outcome for anyone involved.

Chris Henchy and Brooke Shields (married 2001 – present)

Brooke flew into the show for special guest appearance as Alan’s blind date, Danielle. The model had already been married to tennis player Andre Agassi for two years, but the pair filed for divorce in 1999. Two years later Brooke was walking back down the aisle with Chris Henchy. Chris is also an actor who is best known for his Will Ferrell films, such as Daddy’s Home and The Other Guys. Thankfully for Brooke, this time it has worked out as the couple have been married for the last seventeen years.

Stephen Ringer and Aly Michalka (married 2015 – present)

Before her time in the show, Aly made her claim in Hollywood as Keely for the Disney Channel show, Phil of the Future. Aly is also the other half of the musical sister group Aly and AJ. it was in 2013 that Aly first got the chance to appear in TAAHM as Brooke, a role she continued to play for five episodes. Since her time on the show, Aly has said “I do” to writer/director/cinematographer Stephen Ringer who has directed various indie films over the years.

Brad Paisley and Kimberly Williams Paisley (married 2003 – present)

During season eleven we were introduced to Alan’s ex-girlfriend, Gretchen. While the show was one of the smaller roles of her career, the actress has been used to life in the spotlight ever since 2003. Fifteen years ago the actress tied the knot with the country music legend, Brad Paisley. According to Brad, he fell in love with Kimberley after seeing her star in the comedy movie, Father of the Bride. At 19 years old, the singer cast the actress in his I’m Gonna Miss Her music video, and the rest is history.

Sean Penn and Emmanuelle Vaugier (2015 – 2016)

Both Sean Penn and Emmanuelle Vaugier had roles in TAAHM over the years as Sean guest starred as himself as part of Charlie’s men’s group. It wasn’t long after Sean’s breakup from actress Charlize Theron that he was seen cuddled up to his TAAHM co-star. Reports say the pair were holding hands and whispering to each other, with other sources confessing they were in a relationship for a year. However, neither of the two ever confirmed the rumors.

Jimmi Simpson and Melanie Lynskey (married 2007 – 2014)

In the background, or the bushes, of the show was one of the leading characters: Rose. Even though she was Charlie’s stalker, you couldn’t help but love her. Back in 2007, Melanie, who played Rose on the show, walked down the aisle with Jimmi Simpson. The actor is best known for his stints in the sitcom It’s Always Sunny in Philadelphia, and the thriller shows House of Cards and Westworld. Although their divorce was finalized in 2014, the media dubbed it at the nicest separation; the pair didn’t use lawyers and settled everything themselves.

Julia Stambler and Charlie Sheen (dating 2017 – present)

Even though this star has been in the headlines for his many failed relationships over the years, it looks as though Charlie has finally found someone to settle down with. At 26 years old, model Julia Stambler is officially half of Charlie’s age, but it doesn’t look as though either of the pair are bothered. In fact, Julia has defended her boyfriend over the years as well as pushing friends away that have raised concerns about his illness.

“Stalker Sarah” and Angus T. Jones (dating 2012 – present)

Over the years we got to watch Angus grow up as he starred as the half from TAAHM. Sadly, by the tenth season, the actor chose to leave, even going as far as to trash talk the show. As if that wasn’t enough, Angus had even more shocking revelations in store for the world when he announced his new girlfriend: “Stalker Sarah”. Sarah has become famous for her many photos with celebrities over the years, but no one expected this outcome after bumping into Angus.

Eric Michael Zee and Ming-Na Wen (married 2005 – present)

On TAAHM, Ming-Na played the character, Judge Linda Harris. As with many women on the show, Linda fell victim to Charlie’s womanizing ways. What started out as a close friendship between Linda’s son and Charlie soon escalated to a relationship between Charlie and Linda. Sadly for the judge, a picture of Charlie having a taste of her ear came out after she won the award for Judge of the Year. Thankfully, Ming-Na has a much simpler love life in reality as the actress have been married to Eric for nearly thirteen years.

Greg Coolidge and Brooke D’Orsay (dating 2012- present)

Way back at the beginning of the show we were introduced to one of Charlie’s many girlfriends, Kate, played by actress Brooke D’Orsay. The character made several reappearances over the years, including cropping up in the tenth and eleventh season when she began dating Walden. In reality, this actress is a lot more refined as she likes to keep her private life away from the media. Although we know she is in a relationship with Greg Coolidge, there are unconfirmed rumors the pair have already tied the knot.

Casey Anderson and Missi Pyle (married 2008 – 2013)

Jake’s fifth-grade teacher, Delores Pasternak, was another woman on TAAHM that feel for Charlie’s charming ways. Sadly, the teacher believes that she is in a long-term relationship with her new boyfriend who is only looking to have some fun, Charlie doing as Charlie does breaks it off with Delores before the romance goes any further. This doesn’t go down well. One nervous breakdown later and Delores has lost her job. In reality, Missi has also gone through a breakup of her own as she divorced survivalist and naturalist Casey Anderson after five years of marriage.

Bodhi Elfman and Jenna Elfman (married 1995 – present)

A year before appearing in TAAHM, Jenna Elfman wrapped up filming the five-year-long sitcom that forged her career: Dharma and Greg. The actress played the title role for the entire run of the show before being cast as Frankie for two episodes in the first season of TAAHM. Way back in 1991 before either of her hit shows, Jenna starred alongside Bodhi Elfman in a soft drink commercial. The pair instantly hit it off, and have been married for the last two decades.

Adam Rosenblatt and Tricia O’Kelley (married 2007 – present)

Tricia O’Kelley was first cast to play Brooke in TAAHM way back during the first season of the show but didn’t make her grand return until the eleventh season. Even though she didn’t appear in the show, Tricia was able to land roles in the teen drama The Secret Life of the American Teenager, and the sitcoms The New Adventures of Old Christine, and Malcolm in the Middle. In between all her acting work, Tricia met and fell for Adam Rosenblatt. The pair wed in 2007, and are still married over a decade later.

Paul Brown and Nicole Forester (married 2008 – present)

Appearing in TAAHM was the first step along a very successful career for Nicole Forester. The actress played Camille for two episodes in season two of the show. Shortly after, Nicole landed roles in the comedies Will and Grace, and Monk, as well as a part in the sci-fi hit Star Trek: Deep Space Nine, and a leading role in the soap Guiding Light. In 2008, Nicole walked down the aisle with Paul Brown, and the couple have gone on to have two children together.

Denise Richards and Charlie Sheen (married 2002 – 2006)

Over the years Charlie Sheen has hit the headlines for a string of relationships. His real-life womanizing ways gave the actor a head start on TAAHM as his character, Charlie Harper, wasn’t far from the truth. However, in 2002 Charlie put a ring on model Denise Richards’ finger. The pair went on to share two daughters, but sadly the relationship ended after four years. Their initial separation was anything but amicable, but these days the two appear to be back on good terms.

Liam Hemsworth and Miley Cyrus (married? 2009 – present)

Season ten of the show saw country legend Miley Cyrus take one of the starring guest roles as Missi. During her time on the show, Missi catches the eye of both Walden and Jake, but neither is to last. In reality, Miley has gone through a rocky relationship with actor Liam Hemsworth. The pair began dating back in 2009 and were even engaged during 2012. Although the couple later split, things are all back on, and the pair are back together. There are even rumors the two secretly tied the knot. Could they be true?

Theodore Melfi and Kimberly Quinn (married present)

In season five we got to see Kimberly Quinn bring the role of Donna to life for two episodes. Following her stint in the show, Kimberly went on to reprise her role in the crime hit CSI: NY, as well as the drama shows Secret Life of the American Teenager and Grey’s Anatomy. In reality, the actress has tied the knot with screenwriter Theodore Melfi. Some of Theodore’s work has even starred the legendary actor Bill Murray.

Anthony Michael Jones and Alicia Coppola (married present)

While Alicia may have no relation to the famous director Francis Ford Coppola, this actress doesn’t need the name to land her roles. Back in the second season, Charlie tries to woo Alicia’s character, Dr. Michelle Talmadge. However, his plan flops when Charlie hasn’t realized the pair used to date. In real-life Alicia had much more control over her love life as the actress has married producer, writer, and actor Anthony Michael Jones. The pair currently share three daughters together.

Dr. Marc Mani and Heather Locklear (dating 2013 – present)

Sitcoms wouldn’t be complete without the addition of Heather Locklear somewhere. In TAAHM, the actress took on the role of Laura Lang who works as Alan’s divorce lawyer. However, when Charlie seduces Laura, things begin to go wrong. Back when Heather was in high school she met and fell for Marc Mani, but ended up going through a string of failed marriages instead. A few years and one fraud charge for the doctor later and the pair are happily engaged.

Lisa Joyner and Jon Cryer (married 2007 – present)

The show would have been nothing with Alan, the other half of the Harper clan. Although the actor has starred in various productions over the year, the world will forever recognize Jon Cryer as Alan Harper. The actor tied the knot for the second time in 2007 when he met and fell for celebrity gossip and news reporter, Lisa Joyner. Hopefully, Lisa hasn’t dug up any dirt on her new beau as the pair adopted a daughter together in 2009.