The off-screen relationships of the Two and a Half Men cast

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Let’s face it, we have all wondered about the off-screen lives of our favorite characters in film and TV. There is something that fascinates us with the lives of celebrities, especially those that play recurring roles on television shows, because those are the ones we feel like we really “know.” When it comes to TV shows that span over several years, die-hard fans can often become obsessed with the on-screen lives of those we have come to “grow up with.” Of course, we all know that they are just actors and actresses, and that they aren’t really the people who they portray on our TV screens. However, we are still shocked when we find out that these people who we thought we knew so well, actually have lives of their own! How dare they! One of those shows that made us feel at home, was the long-running sitcom Two and a Half Men.


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The show was a huge hit from the first season, and we got to watch the Harper brothers and Jake grow up and develop into deeper, more complicated and meaningful characters along the way. Of course, it wasn’t only the two (and a half) men who we adored, it was also the dozens of women who played the show’s girlfriends, ex-wives, fiancés, moms, etc. What would the show have been like without the entertaining, unique, hilarious and strong women of Two and a Half Men? And who would the Harper brothers be without the many women who put them in their place?

Twelve years have passed since the series finale, and most of your favorite characters on Two and a Half Men are now married (or divorced) with kids or in serious relationships. While some on this list married or dated famous singers or actors, others chose to be with average non-famous people. One on this list is even dating their former stalker…

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Charlie Sheen and Denise Richards (divorced) 2002-2006

Charlie Sheen aka Charlie Harper on TAAHM, has made headlines with his many relationships. One of his most famous was with model turned actress Denise Richards (who also made an appearance on the show). Although the couple had a pretty messy divorce in 2006 after a somewhat brief marriage, they are putting their past behind them and doing pretty well at co-parenting their two daughters Sam and Lola. They frequently spend time together, along with Denise’s adopted daughter Eloise, as a family.

Holland Taylor and Sarah Paulson (dating) 2015-

Holland played the conceited and self-centered mother of the Harper brothers. Since 2015, Holland has publicly announced that she is dating the stunning American Horror Story actress, Sarah Paulson. Although there are over 30 years between the two, they don’t seem to mind. Holland recently called the relationship the “most wonderful and extraordinary thing” to ever happen in her life. And Sarah admitted that she is absolutely “in love.”

Ashton Kutcher and Mila Kunis (married) 2015-

Ashton replaced Charlie in the 9th season of TAAHM. Of course, he is no unfamiliar face in the world of acting. In 2015, he married his former That ’70s Show on-screen girlfriend Mila Kunis. The two are now one of Hollywood’s most adorable power-couples around, and also the doting parents to their two children; a 3-year-old daughter named Wyatt and 1-year-old son named Dimitri.

Marin Hinkle and Randall Sommer (married) 1998-

Marin played Alan’s ex-wife, and mother to Jake, Judith. Although she is known for her failed marriages on TAAHM, in real life it is quite the opposite. She has been married to her theater director husband Randall Sommer, since 1998. The two dated for a whopping 6 years until they decided to tie the knot, and they are still going strong after all these years. Talk about relationship goals.

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

Courtney played Alan’s on again off again girlfriend Lyndsey on the show, but in real life she is in a nice and steady relationship. After a short, one-year marriage with Andrew Conrad from 2000-2001, the actress settled down with Roger Fishman, the president of video-marketing agency Zizo Group, who she has been married to since 2007. A year after they got married they welcomed their first child, a son named Jacob.

Ryan Stiles and Patricia McDonald (married) 1988-

Ryan played Judith’s second ex-husband and friend of Alan, Dr. Herb. Before appearing on TAAHM, he was well-known for his spot-on and hilarious improv on the show Whose Line Is It, Anyway? At the very start of his acting career, in 1988, Ryan got married to a woman named Patricia McDonald. The two met at Punchlines Comedy Club where Ryan was performing stand-up and Patricia was working as a waitress. The couple have been going steady ever since and now have three children together.

Amber Tamblyn and David Cross (married) 2012-

Amber Tamblyn played Charlie’s illegitimate daughter and niece to Alan. In 2012, she married actor David Cross, who is known best as Tobias in the popular TV series Arrested Development. At 53-years-old, David is almost 20 years her senior, but they don’t mind one bit! On February 15, 2017, the two lovebirds welcomed their first child together, a precious baby girl named Marlow.

D.B. Sweeney and Ashley Vachon (married) 2000-

D.B. played Lyndsey’s former fiancé and Alan’s friend. The actor has been married to his lovely blonde wife, Ashley Vachon since 2000. Ashley, who is originally from Texas, works as a writer and is most well-known for her books Pregnancy Romance and Billionaire’s Romance. The pair are now the parents of two teenagers, a 13-year-old daughter named Cody and a 16-year-old son named Cade.

Sophie Winkleman and Lord Frederick Windsor (married) 2009-

Sophie played Walden’s British ex-girlfriend Zoey, and is now married to someone even more wealthy (and royal) off-screen. In 2009, she married Lord Frederick Windsor, who is a financial analyst as well as the son of Queen Elizabeth II’s first cousin Prince Michael of Kent. This makes Sophie (formally) Lady Frederick Windsor. The royal couple have one 4-year-old daughter who was given the long name, Maud Elizabeth Daphne Marina Windsor.

Graham Patrick Martin and Ginny Gardner (dating) 2014-

Graham played Jake’s best friend and Lyndsey’s son Eldridge on TAAHM. He is now well-known for his recurring role as Rusty Beck in the TNT series Major Crimes. Since 2014, he has been in a relationship with 22-year-old actress Virginia or “Ginny” Gardner. The young actress got her first big break on the series The Goldbergs where she played the recurring character Lexy Bloom, and has appeared in a few minor roles in TV shows and movies since then.

Judy Greer and Dean E. Johnsen (married) 2011-

Judy played Walden’s ex-wife Bridget, but is known now for her roles in the Planet of the Apes movies and as the voice of Cheryl on Archer. In 2011, she married television producer Dean E. Johnsen, who is known for producing the shows Real Time with Bill Maher and ABC’s Politically Incorrect with Bill Maher. Dean, who happens to be an avid Planet of the Apes fan, and Judy, who was in the films, decided to have a Planet of the Apes themed wedding in LA, where 200 of their closest friends and former cast mates attended.

Jon Cryer and Sarah Trigger (marriage #1) 1999-2004

Jon was married to his first wife, retired actress Sarah Trigger, for five years until they divorced in 2004. In 2000, they welcomed their first (and only) child together and named him (ironically) Charlie. The two had an ugly divorce and courtroom battles years later. In 2014, Sarah asked Jon for a whopping $88k a month in child support for their son, but was turned down by the judge.

Emmanuelle Vaugier and Chuck Lorre (dated) 2010-2012

Emmanuelle played a recurring role as Charlie’s dance teacher ex-fiancé. From 2010-2012, she was in a relationship with Chuck Lorre aka producer of TAAHM. Emmanuelle dumped her producer boyfriend after finding out that he was seeing another woman behind her back while she was working out of town. Chuck has moved on after the break up, and is currently writing/producing two hit CBS TV shows, The Big Bang Theory and Mom.

Kelly Stables and Kurt Patino (married) 2005-

Kelly played the role of Alan’s sweet receptionist and ex-girlfriend Melissa. In 2005, before her appearance on TAAHM, the blonde bombshell got married to screenwriter/producer Kurt Patino who wrote and produced a number of short films such as Cup O’Joe and Soul Fire Rising. He is also the manager of Burbank-based talent agency, Patino Management Company. The couple has two sons together, named Kellen and Kendrick.

Jennifer Taylor and Paul Taylor (married) 1997-

Jennifer played another one of Charlie’s ex-fiancés on the show, but in real life she has been in a happy relationship for the last 20 (!) years. Jennifer got married to songwriter Paul Taylor in 1997, when she was only 25-years-old, and the couple are as happy as the day they first met. The strong duo are also the parents to two children, a daughter named Samantha and a son named Jake.

Jenny McCarthy and Donnie Wahlberg (married) 2014-

The famous Jenny McCarthy made a guest appearance on TAAHM as the manipulative con-artist Courtney Leopold. She has been married to her second husband, Donnie Wahlberg, since 2014. Donnie is famous as one of the founding members of the ’80s boy band sensation New Kids On The Block. He is also famous for being the older brother to fellow movie star Mark Wahlberg, who holds a very close resemblance to his big bro! Donnie is now focusing on his acting career, and is currently playing himself (alongside Jenny) on the series Return of the Mac. He also is currently playing Det. Danny Reagan on the CBS series Blue Bloods.


Clark Duke and Amanda Crew (rumored) 2008

Clark played Walden’s nerdy friend and roommate on TAAHM, but before that he was known for his roles in the comedy film Hot Tub Time Machine and the ABC Family series Greek. Although Clark tends to play socially-awkward characters who can’t land a girlfriend, he was rumored to be dating his gorgeous former costar Amanda Crew during 2008. While the relationship was never made public, it was hard to deny the pair’s chemistry on and off screen.

Maggie Lawson and Ben Koldyke (married) 2015-

Maggie played the quirky and adorable social worker Ms. McMartin, who was assigned to Walden and Alan when they chose to adopt a child. In 2015, the actress best known as Det. Jules on Psych, got married to actor Ben Koldyke. The couple met while costarring in the ABC sitcom Back in the Game. Ben is now famous for his current role as the lead in the NBC series Mr. Robinson.

Rachel Cannon and Noah Engh (married) 2013-

Rachel appeared in only one episode as Charlie’s girlfriend Chloe, and love interest of fellow guest star Fernando aka Enrique Iglesias. The beautiful blonde, who is currently playing Deidre in the ABC comedy Fresh off the Boat, got married in 2015 to Noah Engh. Noah is a Canadian Indie singer/songwriter who is also known as “The Kid Fantastic.” While the couple have mostly stayed out of the limelight, Rachel does occasionally share photos of her husband and their adorable little boy named August on her Instagram page.

Ashton Kutcher and Demi Moore (divorced) 2005-2013

Before Ashton was married to his current wife/mother of his beautiful children Mila Kunis, he was married to actress Demi Moore. The two split after 8 years of marriage after Demi found out Ashton cheated on her with a young woman named Sara Leal. The two had a pretty nasty divorce that took over a year to be finalized, and Sara, who was just an average 22-year-old girl at the time, said she deeply regretted getting together with Ashton and even said that it ruined her life! Ouch.

Brooke Shields and Chris Henchy (married) 2001-

The exquisite model turned actress Brooke Shields played Danielle and Alan’s blind date in a guest appearance on TAAHM. Brooke has been married to husband number two, Chris Henchy, since 2001 and their romance is still going strong 16 years later. Chris is a screenwriter and producer who is best known for his work in several Will Ferrel movies such as The Other Guys, The Campaign and Daddy’s Home- as well as many other films and TV shows. The couple now have two daughters together, Rowan and Grier.

Aly Michalka and Stephen Ringer (married) 2015-

Aly played Jenny Harper’s girlfriend in the 11th season of the show. She is better as the “Aly” in the sister musical duo “Aly & AJ” and formerly as Keely in the Disney Channel series Phil of the Future. Since 2015, she has been married to cinematographer/director/writer Stephen Ringer, who wrote and directed the film Weepah Way For Now (starring Aly and AJ) as well as some other indie films.

Kimberly Williams Paisley and Brad Paisley (married) 2003-

Kimberly was known on TAAHM as Gretchen, Alan’s former girlfriend. If you didn’t already figure it out by her last name, the Father of the Bride actress is married to country music superstar, Brad Paisley. The lovely couple got married in 2003, and now are the parents to sons William and Jasper. They met back in 2001, when a 19-year-old Brad (who had a big crush on Kimberly after seeing Father of the Bride) casted her in his 2001 music video for the song “I’m Gonna Miss Her.”

Emmanuelle Vaugier and Sean Penn (rumored) 2015-2016

Shortly after his very public breakup with Charlize Theron, Sean Penn was spotted looking close and personal with with Emmanuelle at an Oscar award dinner. The two were later seen out and about holding hands and acting very much like a couple. Sources said that the pair were in a serious relationship for about a year, until it ended for unknown reasons in 2016.


April Bowlby and Josh Groban (rumored) 2009-2010

April played the ditzy, young and gorgeous Kandi on TAAHM. The still young and gorgeous actress is still acting today and recently made a guest appearance on The Big Bang Theory. As far as her dating life goes, she tends to live a pretty private life and keeps her relationships out of the limelight. However, she was rumored for having a brief relationship with award-winning singer/songwriter Josh Groban, who is best known for his 2003 song “You Raise Me Up.”

Melanie Lynskey and Jimmi Simpson (divorced) 2007-2014

TAAHM would not have been the same without Charlie’s adorable stalker Rose, played by the fabulous and hilarious Melanie Lynskey. Melanie married actor Jimmi Simpson, who is known for his roles on Westworld, House of Cards, and It’s Always Sunny in Philadelphia (just to name a few) in 2007. Sadly, their relationship ended in divorce in 2014. Fortunately, their divorce made headlines as one of Hollywood’s “nicest divorces ever.” Apparently, they didn’t even hire a lawyer and worked everything out by themselves. If only all divorces could end this well.

Charlie Sheen and Julia Stambler (dating) 2017-

Charlie Sheen is now on to relationship number… we don’t know we have lost track by now, but he does seem happy! As of June 2017, the former TAAHM star started dating 26-year-old model Julia Stambler. If you don’t feel like doing the math, that means that Charlie is exactly double her age! It doesn’t seem like Julia is bothered by his age (or his other.. issues) and says that she is proud to be his girlfriend.


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

The life of Angus T. Jones aka Jake, who literally grew up on TAAHM, took a strange turn of events after leaving the show during the 10th season. In 2012, he bashed the show and claimed that he had a religious awakening. That same year, he shocked everyone by dating “Stalker Sarah,” an internet sensation who is known for following and taking photos with thousands of celebrities. One of those celebrities who she followed just happened to be Angus, who also attends the same church as her. Five years later, the two are still dating.

Ming-Na Wen, Eric Michael Zee (married) 2005-

Ming-Na Wen played the role of Judge Linda Harris on Two and a Half Men, and she dated Charlie for a little bit. Charlie got really close to her son, and a bit too close to Harris. A photo of Charlie licking Harris’s ear surfaced the day after she won the Judge of the Year Award. In real life, Wen is married to Eric Michael Zee. The couple have two children together; a daughter named Michaela and a son named Cooper.

Brooke D’Orsay, Greg Coolidge (dating)-

Brooke D’Orsay played the role of Kate in eight episodes of Two and a Half Men. She went out with Charlie at the beginning of the show, and then made several other appearances in seasons 10 and 11, hooking up with Walden (then played by Ashton Kutcher). Brooke D’Orsay has been keeping her own private life under wraps, but we do know that she has been dating a guy named Greg Coolidge for some time.

Missi Pyle, Casey Anderson (Divorced) 2012-

Missi Pyle played the role of Delores Pasternak, Jake’s fifth grade teacher. Delores dated Charlie for a little while, but then she believes that she is in something long term with Charlie. Being Charlie, he breaks off the relationship, giving Pasternak a nervous breakdown and causing her to lose her job. Missi Pyle used to be married to naturalist and survivalist Casey Anderson. However, despite everything, the couple’s marriage didn’t survive.

Jenna Elfman, Bodhi Elfman (married) 1995-

Jenna Elfman may be best known for her role as Dharma on the hit TV series Dharma and Greg, but she also played the role of Frankie in two episodes of the first season of Two and a Half Men back in 2003. Elfman has been married for over two decades to Bodhi Elfman, a man she met while doing a soft drink commercial in 1991. The couple so far have two sons who they decided to name Story and Easton.

Tricia O’Kelley, Adam Rosenblatt (married) 2007-

Like many of the actresses on this list, Tricia O’Kelley was first introduced to us as Brooke in the first season of the series. She would not return until well into season 11. In the meantime, Tricia O’Kelley took on roles in shows such as Malcolm in the Middle, The New Adventures of Old Christine, and The Secret Life of the American Teenager. She even found time to fall in love and marry a man named Adam Rosenblatt, with whom she has two children.

Nicole Forester, Paul Brown (Married)-

Nicole Forester played the role of Camille at the end of the second season of Two and a Half Men. After that she exploded out onto the television scene, taking roles in Star Trek: Deep Space Nine, Monk, Will and Grace, and even got nominated for an emmy for her work as the lead in the soap opera Guiding Light. She married her husband Paul Brown, a man with whom she has two children; daughter Frances and son Paul III.

Miley Cyrus, Liam Hemsworth (Married?) 2016-

Believe it or not, country-pop superstar Miley Cyrus even played a role on Two and a Half Men. She appeared in several episodes as Missi, appearing in a couple of episodes in season 10. Missi vies for the affection of both Jake and Walden in the show. However, in the real world, Cyrus is only vying for the affection of one guy – actor Liam Hemsworth. The two got engaged, broke up, then got back together. There are rumors the two even got married in a secret ceremony.

Kimberly Quinn, Theodore Melfi (Married)-

Kimberly Quinn played the role of Donna in two episodes of the fifth season. She then went on to reprise roles in CSI: NY as well as The Secret Life of the American Teenager, Grey’s Anatomy, and Gypsy, amongst others. Kimberly is married to a man named Theodore Melfi, a screenwriter whose films have starred people such as Bill Murray. He has even been nominated for an academy award after writing the screenplay for Hidden Figures and St. Vincent.

Alicia Coppola, Anthony Michael Jones (Married) –

Alicia Coppola (not related to Francis Ford Coppola) played the role of Dr. Michelle Talmadge in the end of the second season of Two and a Half Men. Charlie tries to hit on her, but he fails to realize that the two had a previous relationship. Coppola is currently married to Anthony Michael Jones, and actor, writer, and a producer who has appeared in shows such as General Hospital. The couple have three daughters.

Heather Locklear, Dr. Marc Mani 2017-

Heather Locklear played the part of Alan’s divorce lawyer Laura Lang in the second season of Two and a Half Men. Charlie seduces her, and the two have an intimate night together. However, the two decide to keep the relationship a secret from Alan. In real life, Heather Locklear is engaged to surgeon (and convicted fraudster) Marc Mani. The two were high school sweethearts, but after several failed marriages, Locklear decided to go back to Mani.

Jon Cryer and Lisa Joyner (married) 2007-

Jon played Charlie Harper’s brother and roommate Alan Harper. Jon has been in several movies and TV shows, but he will most likely always be recognized for his lovable (and slightly miserable) character on TAAHM. Jon has been married to his second wife, Lisa Joyner since 2007. Lisa has worked as a reporter for celebrity news and gossip in LA for KTTV and KCBS-TV. She also is known for hosting InFANity on the TV Guide Network. The couple are still happily married, and adopted a baby girl in 2009 named Daisy.