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 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.

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.

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.

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.

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.

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 hallucinates seeing his dead wife Janie. He takes it as a sign that he has to take of himself. Steven has broken up with Ashley, so he and Ryan go out on the town. In group, Lauren tells the group she has to pass her real estate exam.

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.

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.

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.

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.

When the group settles on a date for their holiday party, it happens to fall on what Mr. K believes will be the end of the world. Ryan invites Anne along on his annual trip to wine country with Steven and Lauren worries her boyfriend is ready to pop the question.

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 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.

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, still pained from the breakup with Simone, backslides into his old gambling habit, though sternly warned by Lauren to steer clear. But when he receives the life insurance check for his deceased wife, it’s more than he can bear and he starts making bets on anything and everything. Meanwhile Anne meets a stunning, young bookstore clerk, Brittney, who turns out to be all beauty and no brains.

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 woos an attractive group member, but Janie's ghost materializes as he feels great guilt for dating again. Elsewhere, some of the ladies set out to buy a wedding dress for Lauren.

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.

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.