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Following the sudden death of his wife, sports radio personality Ryan King is forced to attend grief counseling. Feeling it unnecessary, he does so reluctantly, and with minimal participation, until it becomes clear that this may actually help him in unexpected ways.
Frustrated with the "all talk, no action" philosophy of Lauren, Ryan urges Sonia to dump her boyfriend. When the consequences get out of control, Ryan realizes Lauren may be wiser than he realized. And while trying to keep busy and avoid being lonely, Ryan makes increasing demands on his assistant, Carrie. Meanwhile, Ryan rekindles George's love of basketball.
Ryan struggles to keep the group and his "real life" separate, but comes to learn he'll get better faster if he really lets them in. Meanwhile, Steven wants to be there for Ryan and help him overcome his loss, but his efforts to do so are awkward and comical.
Ryan is thrilled to be accepted into Jeremy Roenick's hockey game - a game he has been trying to play in for ten years. Unbeknownst to Ryan, he's been invited out of sympathy. Meanwhile, the group creates collages in an exercise that Ryan blows off, and Anne, hesitant on attending a lesbian wedding agrees to bring Ryan as her plus one.
Ryan comes to grips that he doesn't have Janie around to cook or shop for him anymore. The group discovers that Lauren caves under pressure when taking tests and decides to help her study for her real estate certification exam. Meanwhile, Steven has broken up with his girlfriend and enlists Ryan to be his wingman to go out on the town.
Ryan manifests a textbook symptom of the grieving process - compulsive eating - but he rejects the notion that he is a "grief cliché." After meeting the man in Lauren's life, Ryan offers unsolicited advice in getting them to the next stage of their relationship. Meanwhile, Ryan tries to snap Danny out of his robust fantasy life.
Ryan has never liked celebrating his birthday, but when the group plans a scavenger hunt for him, he reluctantly plays along. Meanwhile, Ryan agrees to let Sonia look after Steven after he's undergone a colonoscopy, and Mr. K and Anne bond over their passion for 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 Amy pays a visit to her old college friends Ryan and Steven, the guys unexpectedly begin to compete for her affection. Meanwhile, Ryan invites the support group to the K-Bal offices for Thanksgiving, Lauren's qualifications are tested by Owen's mom and Anne's kids meet Ryan for the first time.
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.
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 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 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.
Despite Lauren's warning to Ryan of no dating among group members, he continues to pursue Simone but each time things heat-up with them, Janie's ghost appears, throwing Ryan off his game. The group helps Ryan deal with the guilt he feels as he starts dating again. Meanwhile Anne, Yolanda, Sonia, and Fausta decide to buy Lauren a wedding dress and use Owen as a body double.
STARS-Ryan's prideful indignation over having to read a live commercial for a male enhancement product causes him to stage a walkout, only to be replaced by Terrell Owens whom he just hired as a temporary assistant. Lauren obsesses over a single low group evaluation score and solicits help from George to find out who gave her the poor rating. Meanwhile Simone invites Ryan to a meditation center where he does everything but calm himself. And in group, it's Anne who helps put Ryan back on track with the truth.
STARS-When Simone tells Ryan not to wear his wedding ring, he can't seem to get rid of it no matter how hard he tries. That doesn't stop him from asking Simone to move in with him, spurred on by an encounter with his sad, middle-aged bachelor friend, Hughie. Meanwhile Anne, desperate for a babysitter, reluctantly accepts Mr. K's offer to fill the job and as a result she grows closer to her kids.
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. Lauren comes to Ryan's rescue by fleecing him at poker and in the aftermath, Ryan bonds with Anne over their respective lost loves.
Ryan's show is rated #1 but even this new, exalted status does not provide the personal happiness he wants in his life. Lauren explains that happiness comes from within and real joy can only be found by helping others. Ryan attempts to achieve inner happiness by helping Danny hook up with Sonia but she fancies the stranger, Carlo instead. Meanwhile Owen and Anne snoop around the house of the strange Mr. K only to leave more disturbed than when they arrived.
Anne offers to set up Ryan with a new acquaintance, Talia, a recent widow struggling to find her emotional direction. When the three go out together, Talia ends up heavily flirting with them both. Meanwhile Lauren accidentally attracts a man away from Yolanda who has gone on an Asian singles cruise to find a man for herself.
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.
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.