Dr Bill Hoffman is a well-renowned therapist. His marriage is ending and his daughter is dating someone as old as he is. In Bill's group therapy sessions, he gives advice to his patients, while trying to fix his own life's problems.
Bill tells his group to take a risk this week. He follows his own advice and breaks into his ex-wife's house to reclaim his mattress with Petey, a therapist friend, and one of Petey's clients. Dave tries to earn respect from his co-workers. Darlene and Michael try to spend the night together, but are interrupted by Jonathan who needs their help. Inger takes risks that wind up getting her numerous illnesses.
While in Group Therapy for Group Therapists, Bill discovers that his competitiveness may have led to his divorce. He decides to try and change his ways to win Anne back. Inger meets her online gaming husband, who happens to be three teenaged boys. Darlene takes some pictures for her real estate business. Bill believes Jonathan is lying about being able to run a six-minute mile.
Bill tells his group to find their voice. To try and get Anne back, he gets his band of fellow therapists, Pink Freud, to play in public. Jonathan speaks up in the locker room at his gym. David gets his repressed mother to open up.
Bill tells the group to nuture their relationships. He attends his daughter's birthday party and competes with his estranged wife's new boyfriend. Inger doesn't take the hint that her boyfriend doesn't want to go out with her anymore. Michael and Darlene fight. Jonathan tries to take his barrista friend to a Knicks game.
Bill is upset to find out that Inger has a life coach. When he goes to confront the life coach, he finds that she is attractive and wants to sleep with her. Jonathan is irritated with a gay man in his office, so he tries to get him fired.
Bill takes on a new client - a boxer named Kevin who has pent up rage. When he brings him to the group, the boxer gets inexplicably angry at Dave. Bill brings Dave to the boxing ring to help Kevin. Meanwhile, Inger meets an Asian guy on J-Date who is not Jewish.
Bill learns that Dave is dating his daughter Sasha. Although glad that she is not with Ira anymore, Bill is determined to break Sasha and Dave up. However, Raquel helps Bill realize he must use reverse psychology. Sasha breaks up with Dave and gets engaged to Ira. Meanwhile, Darlene tells Michael she won't see him anymore and Inger gets involved with her noisy neighbors.
Bill tries to re-enter the dating world. Dave gets invited to a work party of a girl he really likes. However he accidently eats his roomate's marijuana brownies before the party. Jonathan invites the group out for yogurt on his birthday. Darlene is upset with Michael because he forgot their anniversary.