Taylor, whom Norm has helped stop being a hooker in the first season, starts her new job, as a social worker in the office, but Mr. Denby thinks she's succumbed to the siren call of hookerdom. Norm gets Laurie to help him hit on Shelly, the new probation officer in the office.
Realizing his wiener dog, Wiener Dog, can make $200 dollars a breeding session, Norm sets out to make some fast money off his dog to buy a baseball card for a young boy Shelly is a big sister to, so he can impress Shelly.
After Norm's relapse into gambling winds up having he, his brother, and his friends jailed, Laurie tries to break his addiction. Unfortunately, in order to bail out his brother, being held on thousands in unpaid parking tickets, Norm must see his bookie to collect on a win. Denby's marriage comes to an end, leaving Taylor blamed by Denby. Taylor's probation is up and she awaits decision whether she will be kept on the staff.
Norm and Denby try to pick up women to get over ex's; Denby's failed marriage and Norm's ended relationship with Shelly whom moved to Colorado. Heads butt when Denby and Norm win dates with the lady Norm has been trying to get.
It's the Secret Santa drawing at the office for Christmas and Danny gets Taylor, but things go wrong when Taylor is shocked and made uncomfortable by the gift she gets. Norm and Artie try to bring a merry Christmas to Laurie, whom doesn't like the holiday.
Laurie sets Norm up with a surprise date and when things go south, the two wind up usurping somebody's else limo that's going to a music awards ceremony, where the two become romantically involved. Taylor and Danny's relationship gets more serious.
In this episode, viewers are encouraged to pick up on 50 references to classic movies. Norm confronts his fear of doctors, Laurie confronts her fear of puppets; Danny confronts his fear of public speaking; Artie confronts his fear of peeing in front of strangers.
Norm tries to think of a way to pay for Jenny's veterinarian school studies. Jenny's fiancé takes his revenge upon Norm for stealing her away at the alter. Taylor, Laurie, and Danny enlist Denby's help with a dead man.
Danny becomes jealous when an old football player Taylor knew, shows up at the office as a new employee. Laurie struggles to understand why she doesn't win an award for being one of the best social workers, and seeks advice from her old teacher.