While Bill goes out with Linda, he becomes intimidated when he discovers that she's a former UN ambassador. Meanwhile, Michael is told by a board member of his co-op that his overly frisky dog -the Sheriff- must be neutered and Darlene bonds with her lesbian sister's girlfriend.

Bill's advice to the group this week is to look for new beginnings, but Bill puts his new relationship with Linda at risk when he tries to make ex-wife Anne jealous at a homeowners association meeting. During the meantime, Dave tries to help out his lazy older brother who has been forced to move out of his mom's house while Inger offers employment to Darlene who lost her job.

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.