Norm meets a girl at a bar and becomes involved her, only to discover she is one of Laurie's clients undergoing counseling for getting involved in relationships just to get the attention of her violent boyfriend.
Danny worries over the upcoming of his dad (played by the epic Jack Warden), a strained relationship because the highly masculine father can't relate to his faltering son. Norm befriends Danny's dad only to discover he's gay but in denial.
Norm, Laurie and Danny resolve to start relationships. A fan of Norm loves his hockey bad boy image, Laurie meets a Scottish guy and Danny buys a toupee and is pursued by an attractive woman. But Laurie can't get sleep and Norm is too cute.
Norm gets drunk at a bar with a client and awakens to discover he has checked himself into rehab with the client who is a recovering alcoholic. Norm's supervisor is convinced Norm is an alcoholic and offers him freedom from work duties.
Denby arrives as the new supervisor in the office, taking the position Laurie hoped to get and make positive changes. When Norm gets tricked by Denby into helping him force Laurie to quit, Norm looks for ways to get Laurie to return.
Denby brings his son to the office to learn in a work environment before military school. The son tells Norm he wants to be a chef. Norm says to stand his ground. Denby makes Norm's life difficult unless he supports the military school.
Norm has a regretted fling with an evil office worker Laurie hates. Meanwhile, Laurie is forced to get her driver's license after Denby agrees to her proposed program Meals on Wheels, for which she has put herself down as a back-up driver.
Norm is the new "agony of defeat" on a sports show. He wants to save his image but is blocked from playing hockey because of his gambling. He thinks a grand gesture of social service will gain him a one game exception for a charity match.
To get back into shape for his one-time-only permitted allowance back into hockey, Norm realizes he needs help and enlists his old high school coach, Logan.
Taylor, whom Norm has helped stop being a hooker, starts her new job, as a social worker in the office, but Denby thinks she's still turning tricks. 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.
In order to impress Shelly, Norm tries to get a bunch of toys for the orphan toy donation box Shelly is trying to collect for. Helping him out is his brother, who has just come to town.
Norm tries to convince Shelly to date him and he starts to win her over despite the fact she can't date a client. But then she finds he's been violating his probation requirement of no gambling.
Norm slips and says "I love you" to Shelly so he tries to convince her he uses the phrase with everyone. Laurie runs for city council against an opponent threatening to close half the social service offices in the city. Look for sight gag.
To emerge from the depression he is in because Shelly broke up with him, Norm takes Laurie's advice to help a client (played by Drew Carey) who also has a history of gambling addiction. When trouble ensues, Denby hopes for the worst.
Norm's relapse into gambling lands him, his brother, and his friends in jail. Laurie tries to break his addiction. To bail out his brother, being held on thousands in unpaid parking tickets, Norm must see his bookie to collect on a win.
Norm and Denby try to pick up women to get over ex's; Denby's failed marriage and Norm's ended relationship with Shelly who moved to Colorado. Heads butt when Denby and Norm win dates with the lady Norm has been trying to get.
Norm stumbles upon a self-proclaimed homeless, jobless teen who boxes like an upcoming pro, and selfishly uses him to make money to pay off his bookie.
It's the Secret Santa drawing at the office and Danny gets Taylor, but things go wrong as Taylor is shocked and made uncomfortable by the gift she gets. Norm and Artie try to bring a merry Christmas to Laurie, who doesn't like the holiday.