Episode: 032 | Aired: September 22, 1998
Finch tries to hijack a surveillance videotape of him and Jack's nanny in a compromising position. When Maya has her wisdom teeth pulled, Nina attempts to convince Elliott not to help Maya get home from the dentist.
Episode: 033 | Aired: September 29, 1998
Jack tricks Maya into getting the upstairs neighbor to move so he can build a steam room at work, while Nina frets about the arrival of her old modeling rival and friend.
Episode: 034 | Aired: October 27, 1998
A Halloween episode: Maya discovers how Jack deceived her on Halloween many years ago. Finch swears he's not afraid of the movie Psycho, as Elliott and he try to find out if Nina's friend Binnie really exists.
Episode: 035 | Aired: November 03, 1998
Finch challenges Maya to play a good practical joke. Jack looks into plastic surgery.
Episode: 036 | Aired: November 10, 1998
After Finch conspires to set Maya up on a date with female model, Maya and she turn the tables on him. Meanwhile, after Jack insists that Nina and Elliott treat him just like anyone else at the office, their harsh sarcasm forces him to reconsider his decision.
Episode: 038 | Aired: November 17, 1998
Maya is convinced that her new boyfriend is sending her messages by way of the puppets he uses on his childrens television show. Meanwhile, as Nina invests in an exclusive and trendy nightclub, Elliott regrets sharing his inner thoughts about being a woman with Jack and Finch.
Episode: 037 | Aired: November 17, 1998
Elliott promises to get revenge after Finch is taken advantage of by a woman. Meanwhile, after making a bet with billionaire Donald Trump, Jack enlists Nina to help him lose weight.
Episode: 039 | Aired: November 24, 1998
Jack turns to the staff for ideas to get back on the list of the most influential New Yorkers, while Star Wars's Mark Hamill stalks Finch.
Episode: 040 | Aired: December 08, 1998
Nina is despondent at the retirement of a longtime rival. Jacks desire to gain fame by naming a park after himself backfires. Maya meets a man who constantly takes his shirt off in public. Elliott wears dangerous shoes.
Episode: 041 | Aired: December 15, 1998
Maya fights with Jack over the availability of a "Sneezing Charlie" doll. Finch seeks revenge for a measly Christmas gift. Nina criticizes a handsome mans casual clothes.
Episode: 042 | Aired: January 05, 1999
Maya tries to convince Elliott that his slow-witted brother is a fake. Meanwhile, Jacks efforts to build a shelf for Finch uncovers a pneumatic tube message system hidden inside the office walls, and Nina accepts an influential designers gift of a parakeet.
Episode: 043 | Aired: January 12, 1999
Jack is upset when Mayas old high school boyfriend suddenly reappears. Meanwhile, as Nina nervously prepares for a television talk show, Finch begins interviewing new internship candidates.
Episode: 044 | Aired: February 02, 1999
Mayas efforts to woo a handsome presidential candidate are disrupted when he falls for Nina instead. As Jack decides to give up his private office in order to work among the staff, Finch recognizes that a Six Million Dollar Man doll Elliott stole as a child is now a valuable collectors item.
Episode: 045 | Aired: February 09, 1999
Following his divorce, Finchs dad starts dating Nina. Elliott scares Tyra Banks with Jack's stun gun
Episode: 046 | Aired: February 16, 1999
Finch tries coming to grips with his dads engagement to Nina. As Jack prepares to bid on some solid gold golf tees once owned by Ernest Hemingway, Elliott asks him to speak with Tyra Banks and explain the stun gun incident.
Episode: 047 | Aired: February 23, 1999
Mayas plan for a murder mystery theme party backfires when a grouchy neighbor dies on her doorstep.
Episode: 048 | Aired: March 02, 1999
When Maya gives him Elliotts birthday present to wrap, Finch plays a practical joke by switching it with Perskys gift. Meanwhile, a racehorse Jack co-owns with singer Robert Goulet begins acting up.
Episode: 049 | Aired: March 23, 1999
Finch tries to keep from being identified as the magazines new advice columnist. A mistake forces Nina to have lunch with an acquaintance she doesnt really like. Elliott offends one of the magazines biggest advertisers.
Episode: 050 | Aired: April 06, 1999
Maya and Elliott clash with each other when her photography teacher asks her to do a nude self-portrait. Meanwhile, though Nina hires a new assistant, he spends all of his time entertaining Jack with magic and annoying Finch.
Episode: 051 | Aired: May 04, 1999
Though happy to have been nominated for a Fashion Magazine Excellence Award, Maya is stunned to learn that it was for an article her father chose instead of the one she submitted. Elliott admits that the photo for which he was nominated was actually taken by a monkey. Nina struggles to come up with an acceptance speech. Finch schemes to get seated next to a model.
Episode: 052 | Aired: May 04, 1999
Jack tries to replace Steve Garvey with Maya as pitcher for the offices annual softball game against Cosmo.
Episode: 053 | Aired: May 11, 1999
While Nina suggests Jack hire a personal trainer, Elliott feels left out when Maya and Finch collaborate on a screenplay.
Episode: 054 | Aired: May 18, 1999
Maya challenges Nina to make better choices in life, especially when Nina has to choose between an escaped-convict ex-boyfriend and the FBI agent whos looking for him. Meanwhile, Jack, Finch, and Elliott all start betting on each others habits and idiosyncrasies.
Episode: 055 | Aired: May 25, 1999
To impress an old high school classmate, Finch engineers a date with an emotionally vulnerable supermodel. In a separate effort to make an impression for a magazine article about art in the executive suite, Jack sends Elliott out to buy a suitable painting. But when hes unhappy with Elliotts choice, Jack buys one on his own, oblivious to its sexually charged subject matter.
Episode: 056 | Aired: May 25, 1999
Finch struggles to get married to supermodel Adrienne before her ex-boyfriend finds out. Maya and Elliott argue whether or not Finch and Adrienne love each other