The group is committed to following Bill's rule of the week -- taking a risk. Bill also follows his own rule by using one of Petey clients, a therapist with questionable methods and with whom he shares a waiting room, to help him break into his ex-wife's house to take back their mattress. Meanwhile, Dave tries to earn respect from his co-workers, and Darlene and Michael's rendezvous is interrupted when Jonathan arrives with a problem.

This week advice to the group is about persevering through difficult situations. Bill has his own to deal with when he tries to re-enter the dating scene after 25 years, and invites a pretty woman to an impromptu party but she doesnt show up. Meanwhile, Darlene is upset with Michael because he forgot about their anniversary, Dave accidentally eats some tainted brownies before departing for a co-worker's birthday party, and Jonathan invites the group to a popular yogurt shop in order to bond on his birthday.