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.

Ryan is invited to play a pick-up hockey game with Jeremy Roenick. Later, Ryan finds out it was a setup sympathy invitation. In Group, Lauren has everyone make a collage to express their feelings. Ryan attends a lesbian wedding with Anne.

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.

The group celebrates Ryan's birthday with a scavenger hunt. Elsewhere, Sonia cares for Steven following his colonoscopy, and Mr. K and Anne connect over their love of musicals.

Though Ryan is reluctant to take Owen under his wing, he begins to realize Owen may need a big brother figure in his life. Meanwhile, Yolanda decides she's ready to graduate from the group and Steven hires a new K-Bal Girl.

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 receives an invitation from Bob Costas, his hero, to take part on his new TV show while Fausta invites everyone in the group to her niece's Quincenierra - everyone except Anne. Meanwhile, after completing a major project at work, Mr. K searches to find a new way to contribute and make a difference.

Despite Carrie’s warning, Ryan wants to get his first date out of the way and asks Carrie’s flaky friend, but not without a little competition from Shaun White. Meanwhile, Yolanda starts a new job at the hospital where Sonia works and tries to reinvent herself.

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'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 finds a new rival in the K-Ball Mascot. Also, Ryan is unsure how to handle a flirty, drunk-dial call from his secretary Carrie. In a strange role reversal, Ryan becomes counselor to Lauren in her confused love life while the group prepares a bachelorette party that will never be.