Urn-Ed Run – 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.
Fast Breakup – Ryan becomes jealous of a mascot. In addition, Ryan helps Lauren navigate her perplexing love life, and Ryan receives a boozy, flirty phone call from his secretary.
Matchup Problems – 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 …
Go For The Gold Watch – 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 w…
Double Down – It gets dicey when Ryan falls back into his old gambling habit following a breakup. Elsewhere, Anne meets a sightly young bookstore clerk.
Ring and a Miss – 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.
Go Deep – 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 (Bill Cobbs) to find out who gave her the poor rating. Meanwhile Simone (Piper Perabo) 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.
Pass Interference – 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.
Comeback Player of the Year – 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).
Gooooaaaallll Doll! – Ryan decides to go on his first date, but he’s on a slippery slope when snowboarder Shaun White (playing himself) ends up being his romantic rival. Elsewhere, Yolanda lands a job at a hospital.