Episode: 081 | Aired: October 12, 2000
Elliott accidentally erases a phone message in which Jack's wife says she's leaving him. Finch torments Nina by refusing her sexual advances.
Episode: 072 | Aired: October 19, 2000
Unaware of Jack's impending divorce, Nina and Finch plan a surprise party assuming he and Allie are having a baby. Seeing her dad's divorce as a wake up call, Maya tries, but fails, to get Elliott to read a magazine article about communication between couples. Moving to the Plaza Hotel, Jack tries to avoid everyone.
Episode: 083 | Aired: October 26, 2000
Nina starts dating a popular TV star, only to find that he lives with an overbearing mother. Meanwhile, when Maya presses him to vote in an upcoming election, Elliott is forced to admit he can't because of a prison record that he's kept hidden for many years.
Episode: 084 | Aired: November 02, 2000
When his conniving brother Donnie suddenly returns, Maya warns Elliott to be careful of being conned into giving him money. Finch uses a mind control trick of Jack's to get Nina to admit she broke a prized porcelain cat.
Episode: 085 | Aired: November 09, 2000
Maya's high school best friend, now a motivational speaker, offers to make amends for having falsely accused her of selling out some classmates fifteen years ago. As Elliott presses Maya to go to her class reunion so he can show off an expensive new suit, Jack is disturbed by dreams of being killed by Kevin.
Episode: 086 | Aired: November 16, 2000
Finch discovers that his childhood best friend had a sex change. Elliott tries to get Nina to stop mistreating her new assistant by claiming her father is Calvin Klein; Nina believes him and gets her promoted to be Elliott's boss.
Episode: 087 | Aired: November 23, 2000
Maya's carefully planned Thanksgiving Day dinner takes a turn for the worse when Jack ends up in bed with Elliott's mother. Finch suspects Jack of sleeping with his date, too. Seeing how much Jack is taken with the date's ideas for the magazine, Nina decides she must impress him with her own youthful attitude.
Episode: 088 | Aired: December 07, 2000
After an angry outburst aimed at Jack, Finch is exiled to a distant, and dismal, satellite office. Elliott, after getting a look at Maya's handsome gynecologist at a strip club, suggests she start seeing a female doctor whose office is in the building.
Episode: 089 | Aired: December 14, 2000
When Maya persuades him to adopt a stray dog, Elliott worries that she may be testing his interest in having children; when Jack's regular numbers win the lottery, Finch has to tell him that he never bought the ticket.
Episode: 090 | Aired: January 04, 2001
Finch falls for a female boxer who has a jealous ex-girlfriend. Jack, Elliott, and Nina cheat at the game BrainFever in order to prove they are smarter that Maya.
Episode: 091 | Aired: January 11, 2001
Elliott discovers Finch is his traffic school instructor. Maya and Nina bond at an employee's bridal shower. Jack becomes fascinated with Kevin's pet tarantula.
Episode: 092 | Aired: January 25, 2001
Sensing pressure from Jack, Elliott decides to take Maya to dinner to surprise her with a proposal. When Nina's hometown cancels its Nina van Horn celebration, Maya brings Nina to the dinner. Things come to a head Jack has to get the engagement ring from Finch.
Episode: 093 | Aired: February 01, 2001
After collapsing during his marriage proposal, Elliott tries to convince Maya that he really does want to get married. Finch discovers that Nina rented out Jack's office to make pornographic movies. And in order to keep it a secret from Jack, Nina agrees to give Finch's own autobiographical porn film script to the movie's director.
Episode: 094 | Aired: February 08, 2001
When Maya has a date for a charity auction, Nina sets Elliott up with a high priced call girl. Auctioneer Finch gets revenge on Jack, who has thrown away a gift Finch gave him.
Episode: 095 | Aired: February 15, 2001
As Maya seeks revenge for an intern's heartless remarks, Elliott and Jack struggle to tell Nina that her latest boyfriend is gay.
Episode: 096 | Aired: February 22, 2001
After dropping by the office to speak with Finch about deejaying his upcoming Bar Mitzvah party, a thirteen-year-old develops the hots for Nina and tricks her into attending. Meanwhile, a woman becomes a pawn in Jack and Elliott's game of dating and dumping her.
Episode: 097 | Aired: March 15, 2001
When Maya is attracted to the son of an old family friend, Jack worries that the guy might actually be her brother. Meanwhile, in order to persuade Elliott to continue letting him stay at his apartment, Finch pretends to have been the victim of a burglar's attack.
Episode: 098 | Aired: March 29, 2001
When her younger sister arrives in town, Nina ends up being ignored. Meanwhile, Jack tries to find out who booed him in a speech at the office. This episode contains 3 alternate endings.
Episode: 099 | Aired: April 19, 2001
Finch tries to engineer a romance between his mother and Jack; Elliott and Maya team up to revive the career of a famous photographer.
Episode: 100 | Aired: April 26, 2001
A celebrated romance novelist supplies Finch with toys in exchange for sex; Nina's harsh critique of a disabled star's wardrobe brings some unwanted publicity.
Episode: 101 | Aired: May 03, 2001
Maya discovers that her one-night stand has been hired to work at Blush. Elliott tries to enlist Finch in an effort to change the world by doing nice things for others while Nina bribes him to help her get on their boss's good side.
Episode: 102 | Aired: May 10, 2001
In order to restore their marriage, Jack's ex-wife asks for a job at the magazine. Nina pressures Elliott for an appointment with his therapist girlfriend and inadvertently breaks them up.