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22 Episodes 2000 - 2001
Episode 1
Thu, Oct 12, 200021 mins
Elliot hears Alley break up with Jack on the answering machine. He accidentally erases the message. Finch shares a passionate kiss with Nina and then insults her by telling her she's not his type. Seduction and revenge put Nina on top.
Episode 2
Thu, Oct 19, 200022 mins
Jack checks into Plaza and he can't find any peace and quiet after Maya and Elliot have an argument, Nina comes uninvited and Finch makes a live performance of his boy band.
Episode 3
Thu, Oct 26, 200022 mins
Maya learns of Elliot's criminal past. Nina dates a famous television actor, whose rough-n-tough nomad character melts away once she discovers he lives with his mother. Mamma's not about to share her boy with another woman.

Episode 4
Thu, Nov 2, 200022 mins
Elliot's brother Donnie who once feigned being mentally challenged so that he could be waited on by his mother returns. He claims to have found a job but is in trouble with some loan sharks but Maya is completely skeptical. When he is supposedly beaten up and winds up in a hospital, she thinks it's a con because all of the hospital staff were at the bistro where she and Elliot met Donnie, thinking they were there to make it appear that they were in bistro. So Maya attacks Donnie.
Episode 5
Thu, Nov 9, 200022 mins
Maya's high school friend tells her he is responsible for a bad rumor that caused her unpopularity. He's come back to make it up to her. Jack dreams about Kevin killing him. His nightmares continue until he confronts Kevin in an elevator.
Episode 6
Thu, Nov 16, 200021 mins
Finch meets up with an old friend and is ashamed of his feelings; whilst Elliot gets back at Nina for treating her assistant badly.
Episode 7
Thu, Nov 23, 200021 mins
Everyone will spend Thanksgiving at Jack's country house.
Episode 8
Thu, Dec 7, 200022 mins
When Jack makes Dennis do frivolous errands, Dennis has a meltdown. Jack then sends him to another department where he learns is where Jack sends anyone he gets ticked off with. And Elliot is uncomfortable when he meets Maya's gynecologist who is a good looking guy. He asks her to get another one but she refuses. He later catches the man in a strip club and when he tells Maya she doesn't believe him.

Episode 9
Thu, Dec 14, 200022 mins
Maya and Elliot take in a lost dog. Everything is fine until Finch convinces Elliot that Maya has gotten the dog to test his fatherhood skills. Meanwhile Jack wins the lottery but Finch never bought the ticket in the first place.
Episode 10
Thu, Jan 4, 200122 mins
Finch dates a female boxer with a jealous ex-girlfriend. Elliott, Jack and Nina fool Maya into believing that they're smarter than she is.
Episode 11
Thu, Jan 11, 200122 mins
Maya and Nina have a quarrel over the intentions of giving out invitations to the bridal shower.
Episode 12
Thu, Jan 25, 200122 mins
Elliott's impulsive decision to propose to Maya has dire consequences.
Episode 13
Thu, Feb 1, 200122 mins
Maya gives Elliott the ring back. Elliott proposes again and passes out again. Maya comes to the realization that Elliott is not interested in what she is and kicks him out of their apartment.
Episode 14
Thu, Feb 8, 200121 mins
Elliot and Maya go on dates after their breakup. Finch tries to jeopardize the auction of Jack' collection after he feels betrayed.
Episode 15
Thu, Feb 15, 200121 mins
Ashton Kutcher plays a new intern that Finch immediately develops a man crush on, Nina starts dating a magician who creeps everyone out and "boops" Elliot's nose, Pamela Anderson also appears.
Episode 16
Thu, Feb 22, 200125 mins
Finch DJs a bar mitzvah for a kid who has a crush on Nina. Jack and Elliot set their sights on the same woman.
Episode 17
Thu, Mar 15, 200122 mins
Maya and Harrison, a son of Jack's close departed friend become close. Jack gets very nervous, when he looks into the possibility that Harrison might actually be his son.
Episode 18
Thu, Mar 29, 200122 mins
Everyone likes Nina's younger sister Erlene, who comes to New York for a visit. Nina is jealous and plots to give her the boot.
Episode 19
Thu, Apr 19, 200121 mins
When Finch's newly single mom shows up, he tries to fix her up with Jack so that he can be part of Jack's family. He sabotages Jack's current relationship for the plan to take effect. Elliot learns that a once great photographer has been slumming at Nina's, he's now a 'down and out'. So Elliot tries to help him.
Episode 20
Thu, Apr 26, 200122 mins
Finch becomes a boy toy for a loaded, middle-aged novelist. Nina is asked to co-host the American awards.
Episode 21
Thu, May 3, 200122 mins
Nina convinces Maya to stop over thinking her dating life and just go for it. Eliot tries to get Finch to do something good.
Episode 22
Thu, May 10, 200122 mins
Nina pesters Eliot to set up a therapy session with his new girlfriend. Alie wants Jack back.