1. Hit the Road, Jack
Air date: 2000-10-12 · 30 min
After their moment of passion, Finch decides it's a bad idea to take things further with Nina. Nina becomes determined to find out why. Meanwhile, Elliot overhears, and then accidentally erases a message from Allie telling Jack she is leaving him.
Open episode 1 ↗2. A Night at the Plaza
Air date: 2000-10-19 · 30 min
Tired of everyone's pity after the news of his impending divorce, Jack heads off to the Plaza Hotel. When Finch turns up with his new band, Jack loses his cool.
Open episode 2 ↗3. Mum's the Word
Air date: 2000-10-26 · 30 min
Nina begins dating the star of a TV show who has been filming outside Blush 's office. She soon discovers that he lives with his mother, who is determined to destroy their relationship. Elliott confesses to Maya that he once spent a month in jail.
Open episode 3 ↗4. Donnie Returns
Air date: 2000-11-02 · 30 min
Elliott's brother Donnie returns as a successful insurance salesman in need of a loan. Maya, however, remains convinced that Donnie is up to his old tricks, even when he is beaten up. Jack and the rest of the staff discover that silence is not always a good thing.
Open episode 4 ↗5. Choosing to Be Super
Air date: 2000-11-09 · 30 min
Maya's high school friend tells her he is responsible for a bad rumor that caused her unpopularity and that he has come back to make it up to her. Jack dreams about Kevin killing him. His nightmares continue until he confronts Kevin in an elevator.
Open episode 5 ↗6. Brandi, You're a Fine Girl
Air date: 2000-11-16 · 30 min
When Finch reunites with his childhood friend, he is shocked to learn that he had a sex change and is now a woman named Brandi. Elliot gets back at Nina for treating her assistant badly.
Open episode 6 ↗7. The First Thanksgiving
Air date: 2000-11-23 · 30 min
The gang gathers for Thanksgiving at Jack's mansion in the Hamptons. Nina is convinced that Jack will fire her for being unhip. Jack sleeps with Elliott's mom, but Finch is convinced that Jack did the dirty deed with his date instead. And Maya just wants to put the perfect dinner together.
Open episode 7 ↗8. Slamming Jack
Air date: 2000-12-07 · 30 min
Finch is banished to the mailroom after insulting Jack. Elliott tries to prove that Maya's hunky gynecologist is a frequent visitor to strip clubs.
Open episode 8 ↗9. Dog Day Afternoon
Air date: 2000-12-14 · 30 min
Jack's numbers come up in the lottery, but Finch spent the money on coffee instead of the lottery ticket. Meanwhile Maya and Elliot get a dog, but Finch and Nina convince Elliot that Maya is using the dog as a substitute for a baby.
Open episode 9 ↗10. Finch and the Fighter
Air date: 2001-01-04 · 30 min
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.
Open episode 10 ↗11. The Gift Piggy
Air date: 2001-01-11 · 30 min
When the new girl in marketing asks Nina and Maya to her bridal shower, they are convinced the only reason is so that she gets more gifts. Nina confronts Robin, and Nina and Maya end up arguing. Meanwhile Elliot has to go to traffic school and Finch is the teacher.
Open episode 11 ↗12. The Proposal (1)
Air date: 2001-01-25 · 30 min
Jack's engagement ring is returned as part of his divorce settlement. This inspires Elliott to propose to Maya. He agonises over the perfect proposal, but it is almost ruined when a depressed Nina tags along. Elliott convinces her to leave, only to sabotage the event himself by having a panic attack when she accepts his proposal.
Open episode 12 ↗13. The Proposal (2)
Air date: 2001-02-01 · 30 min
Elliott proposes to Maya a second time, and she accepts again. However, Elliott has another panic attack. Maya later decides that she cannot stay with him, and kicks him out of their apartment. Finch discovers that Nina rented out Jack's office for a porn shoot, and demands she show the director a script he has written. The director loves his work, and wants to shoot the film in Jack's office.
Open episode 13 ↗14. The Auction
Air date: 2001-02-08 · 30 min
When Elliot discovers that Maya has a date for the Blush Charity Auction, he asks Nina to set him up with someone to help make her jealous. So Nina sets him up with a doctor but when she can't make it, she hires an escort instead.
Open episode 14 ↗15. Mayas and Tigers and Deans, Oh My
Air date: 2001-02-15 · 30 min
Finch and Maya project their insecurities on the new intern, Dean. Nina is dating the famous magician, Zigmund, who everyone is convinced is gay and Elliot believes is flirting with him.
Open episode 15 ↗16. Sid & Nina
Air date: 2001-02-22 · 30 min
Finch DJs a bar mitzvah for a kid who has a crush on Nina. Jack and Elliot like the same woman.
Open episode 16 ↗17. Where's Poppa?
Air date: 2001-03-15 · 30 min
Jack fears that Maya's new boyfriend may be his illegitimate son from a one night stand many years before. Meanwhile, Finch has been living with Elliott since Maya kicked him out of her old apartment. When Elliott decides that it's time for him to go, Finch goes to long lengths to be able to stay.
Open episode 17 ↗18. Erlene and Boo
Air date: 2001-03-29 · 30 min
Nina's younger sister come to visit, bringing up feelings of jealousy in Nina when the staff falls in love with her. Meanwhile, Jack is determined to find out who booed him during a speech to the office.
Open episode 18 ↗19. Fanny Finch
Air date: 2001-04-19 · 30 min
Finch's mom comes to visit and finds romance. Elliot meets a famous photographer who is down on his luck.
Open episode 19 ↗20. Sugar Momma
Air date: 2001-04-26 · 30 min
Finch becomes the boy toy of a popular romance novelist. Nina says the wrong thing on the red carpet of an award show.
Open episode 20 ↗21. Maya Stops Thinking
Air date: 2001-05-03 · 30 min
Maya picks up a guy in a bar and finds he's not quite who he claims to be. After being the recipient of an act of kindness, Elliot tries to convince Finch to pay it forward to Nina.
Open episode 21 ↗22. At Long Last Allie (1)
Air date: 2001-05-10 · 30 min
Allie returns and asks Jack for a job at Blush, but she has ulterior motives. Nina meets with Elliot's new girlfriend, who is a psychiatrist, but their session means trouble for Elliot.
Open episode 22 ↗