An irreverent yet charming sportscaster who, after a loss, finds solace from members of his mandatory group therapy sessions.
Cast: Matthew Perry, Laura Benanti, Julie White, Suzy Nakamura, Tyler James Williams, Brett Gelman, John Cho, Tonita Castro, Bill Cobbs, Sarah Baker, Seth Morris, Allison Miller
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 (Allison Miller). 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.
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'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 (Seth Morris) hook up with Sonia but she fancies the stranger, Carlo (Ben Falcone) instead. Meanwhile Owen and Anne snoop around the house of the strange Mr. K only to leave more disturbed than when they arrived.
Ryan, still pained from the breakup with Simone, (Piper Perabo) 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, (Annie Heise) 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.
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.
Lauren hands out evaluation forms to her students; someone gives her a low grade and she struggles to find out who did it. Ryan hires Terrell Owens as an assistant while Carey is away. Ryan and Simone try to be the person the other one wants.
Ryan tries to continue a relationship with Simone but he keeps seeing Janie's ghost which prohibits him from moving forward. The women in the group want to wedding dress shop for Lauren, but she is not ready for it.
Simone, a former group member, returns to the group. Everyone is enthused because they all love her. Ryan is afraid she will change the group dynamics. Steven wants to teach Ryan a lesson and enlists the aid of Mr K and Terrell Owens.
Ryan misses the girl stuff he used to do with his wife, so he & Carrie become girlfriends. Ryan decides he is ready to date and asks Carrie's friend. Yolanda gets a job at the hospital but sabotages her own job by acting like a party girl.
Bob Costas asks Ryan to join him on a TV show he is hosting. Fausta invites everyone to her niece's 15th birthday party - except for Anne. Mr K's invention for a rocket trip to Mar's is claimed a success, but does not know his next project.
Mr K is ready for the end of the world when the Mayan calendar ends. He hosts a holiday/world end party. Since Anne is always grieving, Ryan invites her along to the annual trip to the wine country with Steven. Lauren's boyfriend proposes.
Ryan is ready to date again and updates his Facebook status to available. An Olympic beach volleyball winner invites him to meet her friends. It does not work out. Danny helps Sonia find her cat. George celebrates another year of life.
An old friend of Ryan and Steven's from college comes to town. Steven wants to date Amy and wants clearance from Ryan. Ryan is OK with this-until he actually sees Amy again. Ryan hosts Thanksgiving dinner for them and the group.
Lauren announces that Yolanda is graduating from therapy and will have a celebration party. Yolanda realizes she is not ready to leave after all. Meanwhile, Ryan takes Own under his wings as a big brother and helps towards his healing.
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.
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 comes to grips that he doesn't have Janie (Christine Woods) 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 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 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. ball.
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 grad school entrance exam. Meanwhile, Steven has broken up with his girlfriend and enlists Ryan to be his wingman to go out on the town.
A radio sport broadcaster is forced by his employer to attend a support group after the death of his wife.