Kristin Dattilo as Cindy | Then
Cindy was one of the characters that stood out for not getting into bed with Charlie. For a guy that can easily urge any woman to have sex with him, Charlie certainly did not take Cindy’s rejection well.
She ended up being Jake’s first “crush” and ends up being on one of his erotic drawings.
Krista Allen as Olivia Pearson | Then
Though she was already a girlfriend of Charlie in the past, Olivia was formally introduced into the show when Charlie, Alan, and Jake Harper visited their mother at a dinner.
Everything turns out to be a wreck when Olivia and Charlie start talking about their failed relationship. The heated discussion involved Olivia throwing her drink in Charlie’s face, ending the dinner prematurely.
Krista Allen as Olivia Pearson | Now
Krista Allen is a comedian and actress, moving on to being renowned for her appearances in the television series, Days of Our Lives and Baywatch. She’s also recognizable for her appearances on the big screen in Hollywood blockbusters such as The Final Destinations and Anger Management.
In addition to her career in acting, Allen also spends her time headlining across Los Angeles as a stand-up comedian.
Kristin Dattilo as Cindy | Now
Kristin Dattilo went on to establish her career, landing her distinguishable role as Yola Gaylen on The Chris Isaak Show. She also appeared on hit shows like CSI: Crime Scene Investigation, Dexter, Beverly Hills, 90210, Friends, and Veronica Mars.
After taking some time off to take care of her two children, Dattilo is now developing multiple projects in the industry.
Liz Vassey as Kate McLaughlin | Then
Kate is the nice, single mother who was introduced to Charlie at Jake’s soccer game. Upon meeting him, Kate finds it hilarious that Charlie appeared to look wasted and eventually starts hitting it off with conversations.
She made another appearance on the show but as Charlie’s dermatologist, Michelle. The scene ends up being absolutely priceless when she is seen removing a mole off of Charlie’s behind. The two begin to date until Michelle finds out about Charlie’s other woman.