Ryan King, a radio sports personality, returns to work after grieving for his wife's recent death. His boss says he is not ready to return to work and must attend counseling. He reluctantly attends and meets others who also have to move on.

Ryan does not like to be alone in his house. At group, Ryan encourages Sonia to break up with her boyfriend. She does, but then becomes the cat lady. Ryan has to deal with the fallout. Also, Ryan helps George replace a lost basketball.

Ryan does not want to tell his landscaper his wife has died, but the group convinces him he has to do it. The landscaper builds a shrine to Jannie. Meanwhile, the group thinks Ryan does not like to be seen with them outside the meetings.

Grieving causes Ryan to become a compulsive eater, triggering an intervention from the group. Also, the group finds out that Lauren talks to her boyfriend Wyatt about the group members. She brings Wyatt to the group so they can meet him and he can learn about them.

An old college friend arrives, sparking a surprise competition between Ryan and Steven to win her affection. Meanwhile, Ryan takes the gang to the studio for Thanksgiving; Owen's mother scrutinizes Lauren's qualifications; and Ryan meets Anne's children.

When Ryan decides it's time to start dating again, Misty May-Treanor offers to help and invites him to play in a game of beach volleyball with her friends. Elsewhere, George outlives his doctors' predicted life expectancy for him and is ready to celebrate and Danny develops feelings for Sonia.

Ryan fears the group chemistry will change and feels threatened by the return of the very popular and beautiful former group member, Simone (Piper Perabo) who tries to force the group to choose between her and Ryan. Meanwhile Steven and Mr. K buddy bond and along with Terrell Owens, teach Ryan a lesson. Anne prevents Danny from being taken to the cleaners in his divorce.

Ryan stages a work walkout when he's forced to read a commercial for a male-enhancement product. Meanwhile, Ryan hires football's Terrell Owens as an assistant; Lauren receives a low evaluation score; and Simone takes Ryan to a meditation center.

Ryan dates a recent widow. Serving as his "wingman" is Anne, who ends up competing against Ryan for the widow's attentions. Elsewhere, Lauren unwittingly lures a man away from Yolanda.

Worried that his career is in shambles, Ryan travels to New York with Steven to interview as host of a national show, set up for him by Anne. Meanwhile, the group grumbles they're getting nothing out of their sessions and blame Lauren to such an extent that Yolanda and Sonia make up a big problem for her to fix. When both plans crash, the group finds renewed strength from their failures.