Meet the Real-Life Couples of the 'Two and a Half Men' Cast

Yahoo

27-07-2025

Nothing gets in the way of being a womanizer more than when your divorced brother and his jokester young son move into your Malibu home, which is exactly what happens to Charlie Harper (Charlie Sheen). Despite his brother, Alan's (Jon Cryer), unsuccessful romantic history and the limited dating experiences of his friend Walden Schmidt (Ashton Kutcher), behind-the-scenes they weren't so unsuccessful. Get to know the real life couples of the Two and a Half Men cast.
Jon Cryer and Sarah Trigger
Two and a Half Men star Jon Cryer's first marriage was a bit tumultuous. He was previously married to former actress Sarah Trigger from 1999 until 2004. During that time, Cryer and Trigger welcomed a child together, son Charlie, on June 27, 2000.
When the couple decided to split up, it was seemingly amicable until they embarked on a custody battle that turned contentious. Cryer initially won primary custody of their son, but Trigger was later awarded visitation rights. In 2009, Trigger allegedly hired a hitman to kill Cryer, though she denied the claims.
Jon Cryer and Lisa Joyner
In 2007, Cryer tied the knot with his second wife, entertainment reporter Lisa Joyner. Two years later, the couple adopted a daughter, Daisy.
'The key to a good marriage is 100 percent a sense of humor, because whenever there are hard things in a marriage—and there are— laughing about it makes the most wonderful difference,' Cryer said. 'It's about having somebody in your corner no matter what, and I feel so lucky to be that guy for my wife.'
Ashton Kutcher and Demi Moore
Ashton Kutcher met his first wife, actress Demi Moore, during a casual dinner with friends in 2003. The duo had a 15 year age gap at the time—with Moore40 to Kutcher's 25—but they began dating despite it.
In 2005, the couple exchanged vows with one another. After trying to have children, the duo suffered a late-term miscarriage in 2006, about six months into the pregnancy. Although they never had children together, Kutcher had a close bond with Moore's daughters.
The couple announced their split in November 2011, finalizing their divorce two years later.
Ashton Kutcher and Mila Kunis
Ashton Kutcher and Mila Kunis have a love story for the ages. The now married couple first met in 1998 while filming their hit TV show, That '70s Show, where the two portrayed a couple on-screen. However, Kunis was 14 at the time while Kutcher was 20 (she lied about her age when auditioning for the show).
Kunis recalled having a major crush on Kutcher when they first met and their first kiss on the show was Kunis' first ever.
'I was so nervous and uncomfortable,' Kunis said of their first kiss. 'I had the biggest crush on him.' Kutcher shared his own thoughts on it, explaining, 'I was so nervous. She acted so cool. She seemed as if she'd done it a thousand times. I was the one with the butterflies in my stomach.'
The two remained friends throughout the show and afterwards, while both dating and marrying other people. But in 2012, the friends reunited at the Golden Globes and soon after began casually dating. However, things turned serious quickly as they moved in together the same year and became engaged in 2014.
On October 1, 2014, Kunis and Kutcher welcomed daughter Wyatt. Less than a year later, the couple tied the knot on July 4, 2015, and on November 30, 2016, they welcomed son Dimitri. Kunis and Kutcher have been living happily ever since.
Charlie Sheen and Donna Peele
Two and a Half Men star Charlie Sheen met his first wife, model and actress Donna Peele, during an advertising campaign in New York in July 1995. The couple moved quickly and wed just a little over six weeks after meeting, in September 1995.
Their relationship ended just as quickly as it started as they were divorced by 1996. While Sheen's career continued to skyrocket, the model retreated from the entertainment industry.
Charlie Sheen and Denise Richards
Charlie Sheen and Denise Richards first met on the set of Good Advice in 2000, but it wasn't until Richards guest starred on Sheen's series, Spin City, in 2001 that they became close. They began dating in 2001 and quickly became engaged later that year, tying the knot in June 2002.
In March 2004, the couple welcomed their first child together, daughter Sami Sheen. Later that year, they announced they were expecting another child but before their daughter arrived, Richards filed for divorce in 2005. On June 1, 2005, the couple's second daughter, Lola, was born.
While they attempted to save their marriage, things officially ended in 2006.
Charlie Sheen and Brooke Mueller
Not long after his last marriage, Sheen wed actress Brooke Mueller, who he was introduced to by a mutual friend. The couple married in 2008 and were together for about three years, but not without complications.
In March 2009, they welcomed twin sons Bob and Max. During their marriage, there were domestic violence allegations against Sheen, while Mueller struggled with substance abuse. Sheen and Mueller divorced in 2011.
Conchata Ferrell and Arnie Anderson
Conchata Ferrell was in a loving marriage with husband Arnie Anderson for nearly 35 years. The actress married Anderson in 1986 and the two remained together until her death in 2020. They had a daughter, Samantha Anderson, and Anderson had two daughters from a prior marriage.
Holland Taylor and Sarah Paulson
Holland Taylor and Sarah Paulson first met about 20 years ago while at a dinner party, though both were in other relationships at the time. About a decade later, Taylor used social media to get Paulson's attention by sending her a DM, or direct message, on Twitter. Their relationship was confirmed in December 2015.
Despite their 32-year age gap—Taylor is 82 while Paulson is 50—the two have maintained a happy relationship for the past decade.
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