Ep 23. Charlie and the Secret Gigolo

Charlie and the Secret Gigolo is the 23rd episode of the second season of Anger Management. In this episode, Charlie Sheen plays Charlie Goodson, a therapist who helps people with their anger issues, while himself struggling with a rage problem.

The episode begins with Charlie's patient, Lacey (played by Noureen DeWulf), telling him that her boyfriend (played by Derek Richardson) has become distant and she doesn't know why. Meanwhile, Charlie's therapist, Dr. Freeman (played by Jane Lynch), insists that they do a role-playing exercise to help Charlie deal with his anger.

Later on, Charlie is surprised to find out that his daughter, Sam (played by Daniela Bobadilla), has posted a video of him losing his temper and going on a rant. This leads to Charlie getting a phone call from an old friend, Chris (played by Tim Bagley), who needs his help.

Chris tells Charlie that he's been working as a gigolo and he needs Charlie to cover for him for one night. Charlie is hesitant at first, but Chris says he'll pay him a lot of money. Charlie agrees to do it and meets his client, a woman named Sherrie (played by Kerri Kenney-Silver).

Meanwhile, Lacey's boyfriend reveals to her that he's been seeing a therapist and she assumes it's Charlie. She confronts Charlie about it and he denies it, but she doesn't believe him. She follows him to his secret gigolo job and assumes he's cheating on her.

Things get even more complicated when Charlie's ex-wife, Jennifer (played by Shawnee Smith), also shows up at Sherrie's house, trying to get Charlie back. Charlie manages to juggle all of his women, but eventually, he gets caught.

In the end, Charlie admits to Lacey that he's been moonlighting as a gigolo and she surprisingly supports him. Meanwhile, Dr. Freeman is happy with Charlie's progress and awards him with a trophy for completing their role-playing exercise.

Overall, Charlie and the Secret Gigolo balances the show's trademark humor with some genuinely heartfelt moments. The episode offers a fresh take on Charlie's character and explores his vulnerabilities and insecurities. With its strong performances and clever writing, this episode is sure to keep viewers entertained from start to finish.