Bill assigns the group to go out and make connections with other people. Dave tries to make a connection with a woman in his office that he has a crush on, Jonathan tries to make friends with a local coffee house barista, Inger tries her hand at internet dating, and Darlene spends time with a new man she just met who just happens to be fellow group member Michael. Meanwhile Bill discovers that Anne is in a relationship with the guy who sold him his car and that his daughter is dating her psychology professor a man old enough to be her father.
Songs: Paul Simon -- You Can Call Me All
The group goes a bit overboard when they undertake Bills rule of the week in taking a risk. At the behest of Petey, a therapist with questionable methods and with whom he shares a waiting room, Bill takes his own advice. Together with Petey and one of Peteys patients, Bill breaks into his estranged wife Annes house to take back their mattress for his own. Meanwhile Dave attempts to earn some respect from his office co-workers, and Darlene and Michaels rendezvous is interrupted when Jonathan shows up with a problem.
After being informed by colleagues from his Group Group -- group therapy for those who run group therapy -- that his competitiveness may have led to his impending divorce, Bill sets out to change his ways and woo Anne back. Meanwhile, Inger is in for a shock when she meets her online gaming husband, Darlene takes a disastrous stab at advertising for her real estate business, and Jonathan is taken aback when Bill doesnt believe that he can run a six-minute mile.
Bills advice to the group is to find their voice. Bill finds his by getting his band of fellow middle-aged therapists, Pink Freud, to reunite in order to woo Anne back by playing a gig. Jonathon speaks up against male nudity in the gym locker room and Dave finally gets his mother to open up to him about herself but he soon discovers that what she has to say was better left unsaid.
Sashas Birthday BBQ Bills rule of the week is for everyone to nurture their relationships. However, in trying to nurture his relationship with daughter Sasha, Bill finds himself competing with estranged wife Annes boyfriend, Kenny, for Sashas affection at her birthday party; Meanwhile Ingers rendezvous with an internet date goes south after she inadvertently insults him; Jonathan neglects to tell his wife that he has plans to go out with his male coffee barista friend to a Knicks game; and Darlene and Michael take a stab at nurturing their relationship but end up in an argument over the relevance of Tom Hanks.
Bill's advice to the group is to face their insecurities. Despite having completely different philosophies about therapy, Bill falls into a sexual relationship with Inger's crackpot life coach, Krista. Meanwhile, Inger follows Krista's instruction to hug a man, in this case, Dave, for three days in a non-sexual way, Jonathan jealously attempts to sabotage a flamboyant, funny co-worker who is liked by the rest of his colleagues, and Michael tries to prove that he could make just as much money as his clients by writing a screenplay which Darlene is horrified to discover is completely awful.
Bill's advice to the group is not to accept defeat. With his marriage in ruins, Bill decides to take on a new challenge at work -- sports psychology. He takes on a timid boxing client, Kevin. However, when the only thing that seems to stimulate Kevin's rage is physically harming Bill's other patient, Dave, Bill is confronted with an ethical dilemma. Meanwhile, Inger finds herself in a game of Jewish chicken when she dates an Asian man through J-Date -- and neither one will admit they're not Jewish -- and Michael becomes consumed with trying to beat his assistant's record at a Blackberry video game.
Dave starts dating Bill's daughter, Sasha, and Bill sets out to break them up until a colleague gives him some professional advice. Meanwhile, Inger decides to stop her noisy next-door neighbors from fighting; and Darlene breaks up with Michael (who becomes outraged), then meets Sasha's ex-boyfriend Ira , and the two immediately hit it off. After all, they both idolize Bill.
It's party time for Bill and the group. For Dave, it's a blowout thrown by a female coworker he has his eye on, but pre-party hunger pangs do him in. Jonathan invites everyone to celebrate his birthday---by standing in line for hours for frozen yogurt. Inger and the feuding Darlene and Michael show up. And Bill throws a raucous, if boring, beer bash at Anne's house to impress a woman he's afraid to ask out.
Bill goes on a date with Linda, but is intimidated by her when he finds out that she was once a UN ambassador. Meanwhile, Michael is told he must get his dog neutered. Elsewhere, Darlene is able to bond with her sister's girlfriend.
Bill advises the group this week to look for new beginnings, but Bill ends up risking his relationship with Linda after he attempts to make Anne, his ex-wife, jealous during a homeowners' association meeting. Meanwhile, Dave helps his older brother out when their mother forces him to move out; and Inger Darlene a job after she loses hers.