Episode: 103 | Aired: September 27, 2001
Finch gets a job as Snoop Dogg's assistant after Jack fires him for sleeping with Allie. Nina, Elliott, and Maya declare war on Finch's replacement.
Episode: 104 | Aired: October 11, 2001
Betsy, a new security guard, is revealed to be Finch's junior college classmate who he claims was an obsessed stalker who assumed his personality. When Elliott efforts to zealously guard some special cannolis are undermined by his fear of Jack, Maya goads Elliott into confronting him.
Episode: 105 | Aired: October 18, 2001
Elliott regrets convincing Finch to give in to former classmate and current security guard Betsy's advances. After counseling Nina on how to ask for a raise, Maya discovers her own efforts to get more money have been helped by the fact that she's the boss's daughter. But when she takes Jack to task for his favoritism and asks to treated just like everyone else, Maya suddenly finds that she's not getting a raise after all.
Episode: 106 | Aired: October 25, 2001
As Nina grieves over the death of her best friend, Jack takes a liking to a voice activated wireless computer called The Executive Egg. Worrying that the Egg could put him out of a job, Finch announces that he wants to go back to college on a Gallo Foundation Scholarship.
Episode: 107 | Aired: November 01, 2001
Maya hires a smart new assistant who doesn't hesitate to use her beauty as an asset at work. Elliott offers to give Kevin's dismal love life a boost by arranging a blind date.
Episode: 108 | Aired: November 08, 2001
Finch and Elliott battle for the attention of a Maya's assistant, now a writer. Jack pits Maya against Nina in a war of ideas.
Episode: 109 | Aired: November 15, 2001
As their competition for the new writer Amy's attention intensifies, Finch and Elliott are taken aback when she approaches them both for a date. Jack goes to great lengths to get Kevin to accept a promotion but ends up corrupting him.
Episode: 110 | Aired: December 06, 2001
In hopes of persuading him to finance a new cable TV network, Jack allows a wealthy cable TV mogul to humiliate Elliott; Nina enlists Maya to keep Kevin from stalking her.
Episode: 111 | Aired: December 13, 2001
As the office Christmas party gets underway, Kevin is excited to have as his cousin, actor Ray Liotta, as his guest. When Maya and Ray are introduced, she is delighted to discover that he shares her passion for Christmasm but soon discovers the dark side to his holiday obsession. Meanwhile, dressed as Santa, Jack comes to his daughter Hannah's defense by telling a little boy bully that he wont be getting any presents for Christmas this year. Nina and Finch struggle to write a new Christmas carol.
Episode: 112 | Aired: January 10, 2002
After admitting that she was a teenage mom, Nina prepares to meet her long lost daughter and asks Finch to pose as her son. Meanwhile, upon returning from England with a dartboard, Jack challenges a reluctant Elliott to a match, which leads into a prickly situation.
Episode: 113 | Aired: January 17, 2002
Nina discovers that she and her granddaughter have a lot of wild ways in common. Jack, after turning to Finch and Elliott for help in choosing just the right gift, is stunned when Maya spurns his birthday presents.
Episode: 114 | Aired: January 31, 2002
Actor Ray Liotta makes a plea on The Tonight Show to revive his romance with Maya. As Nina readies her one-woman show for The Blue Match Dinner Theater, Finch and Elliott conspire to break Jack of his fascination with his new antique desk once owned by George Washington.
Episode: 115 | Aired: February 07, 2002
Finch creates an imaginary son in an effort to hire an attractive young au pair for himself. Jack submits Elliott to a loyalty test
Episode: 116 | Aired: February 28, 2002
An empty apartment in Maya's building provides the perfect opportunity for Finch and Kevin to be roommates, but Finch opts for his college dorms. Meanwhile, Jack buys the vintage car Elliott has been lovingly restoring since high school.
Episode: 117 | Aired: March 07, 2002
Maya agrees to date Nina's self-righteous, blind ex-boyfriend. When Finch enrolls in a television production class, he invites Elliott to be the first guest on "Finch Attack," his campus TV station talk show.
Episode: 118 | Aired: March 25, 2002
Maya falls in love with the offices dimwitted but hunky exterminator; Finch and Elliott amuse themselves by paying Kevin to eat garbage.
Episode: 119 | Aired: March 28, 2002
Maya learns that Elliott secretly took a photograph of her in the nude. Jack hires Finch a tutor/massage therapist to help him pass his final exams.
Episode: 120 | Aired: April 04, 2002
Jack cancels a vacation to pursue his dream of writing the Great American Novel, then pays an English professor to write it for him. In Jack's absence, Maya, Nina, and Elliott battle over running the magazine.
Episode: 121 | Aired: April 11, 2002
Office infighting in front of designer Kate Spade causes Jack to engage a corporate therapist to work with the staff.
Episode: 122 | Aired: April 18, 2002
A student crew documents the making of Finchs film class project, The Burning House, loosely based on his childhood. As Finch struggles with a cast that includes Nina and actor David Hasselhoff, everyone involved gets an opportunity to weigh in with their own candid observations. However, Jack threatens to derail the film after he demands that Hasselhoff apologize for accidentally scratching his car in the parking lot.
Episode: 123 | Aired: April 25, 2002
As Jack attempts to demonstrate his patriotism, Elliott accuses Finch of stealing his grandmother.
Episode: 124 | Aired: May 02, 2002
Jack uses Maya to try and outdo rival Alan Thicke, landing all of them in therapy. Nina breaks up Finch's air guitar band after she falls in love with the lead guitarist.