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20 Episodes 1999 - 2000
Episode 1
Wed, Sep 22, 1999
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 that she has succumbed to the siren call of hookerdom. Norm gets Laurie to help him hit on Shelly, the new probation officer in the office.
Episode 2
Wed, Sep 29, 1999
Realizing that his wiener dog, Wiener Dog, can make $200 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.
Episode 3
Wed, Oct 6, 1999
To impress Shelly, Norm tries to get a bunch of toys for the orphan toy donation box for which Shelly is trying to collect. Helping him out is his brother, who has just come to town.
Episode 4
Wed, Oct 13, 1999
Laurie helps Norm confront his fear of death after Danny's father passes away, so that Norm can console Danny.
Episode 5
Wed, Oct 20, 1999
Norm tries to convince Shelly to date him and 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.
Episode 6
Wed, Oct 27, 1999
After being blackmailed by her opponent because of Norm, Laurie tosses him out of her campaign and takes up the services of Denby, who proclaims to have worked for Nixon. Norm accidentally says "I love you" to Shelly, and becomes paranoid when Danny and Artie start warning him this will lead to a relationship ultimatum. And then Shelly announces she has a job offer in Colorado.
Episode 7
Wed, Nov 3, 1999
Norm slips and says "I love you" to Shelly, so he tries to convince her that he uses the phrase with everyone. Laurie runs for city council against an opponent who is threatening to close half of the city's social-service offices. Look for a hilarious sight gag.
Episode 8
Wed, Nov 10, 1999
To emerge from his depression after Shelly breaks 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.
Episode 9
Wed, Nov 17, 1999
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.
Episode 10
Wed, Nov 24, 199930 mins
Norm and Denby try to pick up women to get over 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.
Episode 11
Wed, Dec 1, 1999
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.
Episode 12
Wed, Dec 15, 1999
At the office Secret Santa drawing, 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.
Episode 13
Wed, Jan 5, 2000
Danny awaits Taylor'a decision on whether to go out with him; Laurie's twin sister visits--or "the hot one" as Norm dubs her; complications arise.
Episode 14
Wed, Jan 19, 2000
Unable to meet his rent and faced with the landlady moving into his place of her own accord, Norm gets a job as a male escort, which shocks Taylor.
Episode 15
Wed, Jan 26, 2000
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.
Episode 16
Wed, Feb 9, 2000
Norm continues to pursue Jenny although she's engaged; Norm and Jenny's fiancé verbally battle for her love.
Episode 17
Wed, Feb 16, 2000
Things between Norm and Jenny become strained when Norm is worried about getting married after only a couple weeks of knowing each other.

Episode 18
Wed, Mar 1, 2000
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.
Episode 19
Wed, Mar 8, 2000
Norm tries to think of a way to pay for Jenny's veterinary studies; Jenny's fiancé takes his revenge upon Norm for stealing her away at the altar; Taylor, Laurie, and Danny enlist Denby's help with a dead man.
Episode 20
Wed, Mar 15, 2000
Danny becomes jealous when a former football player Taylor knows 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.