Ryan seeks stardom by heading to New York with Steven and interviewing as host of a national show. Elsewhere, the group begin to grumble and crumble when it's believed they're not benefiting from their sessions.
Although his radio show is tops in the ratings, Ryan still can't find personal happiness. He pursues inner peace by trying to romantically connect Danny and Sonia, but she has eyes for someone else. Elsewhere, Owen and Anne explore quirky Mr. K's house.
Ryan's wedding ring causes complications. Meanwhile, Ryan asks Simone to move in with him after he has an encounter with his mirthless bachelor friend; and Anne hesitantly enlists Mr. K as a babysitter.
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 worries that the group chemistry will transform for the worse when a popular and attractive member returns. Elsewhere, Steven and Mr. K bond and teach Ryan a lesson with help from football's Terrell Owens (playing himself).
Ryan is invited to be part of a new TV show featuring his hero, Bob Costas (playing himself). Elsewhere, Fausta invites everyone except Anne to her niece's birthday celebration, and Mr. K completes a major project, then seeks a new way to contribute.
The gang throws a holiday party, but the bash falls on the same day Mr. K believes the world will end. Meanwhile, Anne tags along on Ryan's annual getaway to wine country, and Lauren fears her boyfriend will propose to her.
Ryan decides to date again and receives an invitation from Olympian Misty May-Treanor (playing herself) to play beach volleyball with her pals. Meanwhile, George celebrates living beyond his life expectancy, and Danny begins falling for Sonia.
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.
Grieving causes Ryan to become a compulsive eater, triggering an intervention from the group. Meanwhile, Ryan offers romantic advice to Lauren, and Ryan tries to pull Danny out of his sweeping fantasy world.
Ryan is invited to play in a hockey game featuring Jeremy Roenick (starring as himself), but he's been chosen out of sympathy. Elsewhere, the group creates collages in an exercise that Ryan finds useless; and Ryan accompanies Anne to a lesbian wedding.
Ryan goes against Lauren's mode of operation and takes action to solve Sonia's problem, but his efforts backfire. Elsewhere, Ryan showers his assistant with demands, and Ryan reconnects George with his love of basketball.