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- Season 5 overviewOct 12, 2000-May 10, 200122 episodesSeason 5 episodes1. Hit the Road, Jack Oct 12, 2000
- Finch avoids Nina; she has other plans; Elliot erases Jack's message.
- 2. A Night at the Plaza Oct 19, 2000
- Finch tries to raise Jack's spirits with an impromptu performance by his new band.
- 3. Mum's the Word Oct 26, 2000
- Nina begins dating a famous actor whose mother is determined to keep her away.
- 4. Donnie Returns Nov 2, 2000
- Elliott's scheming younger brother returns, claiming to be a successful insurance salesman.
- 5. Choosing to Be Super Nov 9, 2000
- Maya's high-school friend is hired to give a motivational speech.
- 6. Brandi, You're a Fine Girl Nov 16, 2000
- A boy, who was Finch's best friend in childhood, is now a woman.
- 7. The First Thanksgiving Nov 23, 2000
- Jack has a fling with Elliott's mother before Thanksgiving Day dinner.
- 8. Slamming Jack Dec 7, 2000
- Finch is exiled to the basement, where he discovers Jack's first assistant.
- 9. Dogday Afternoon Dec 14, 2000
- When Jack's lottery numbers come up, Finch has to tell him he spent the ticket money on coffee.
- 10. Finch and the Fighter Jan 4, 2001
- Finch dates a female boxer and gets into trouble with her jealous ex-girlfriend.
- 11. The Gift Piggy Jan 11, 2001
- Nina and Maya fight over the intentions of a bridal shower invitation.
- 12. The Proposal Jan 25, 2001
- Elliott decides to propose to Maya, but mishaps complicate his plans.
- 13. The Proposal Feb 1, 2001
- Elliott's fear of marriage antagonizes his relationship with Maya.
- 14. The Auction Feb 8, 2001
- Elliott attends a charity auction with a professional escort (Lucy Lawless).
- 15. Mayas and Tigers and Deans, Oh My Feb 15, 2001
- Maya disapproves of the new intern's handling of his girlfriend.
- 16. Sid & Nina Feb 22, 2001
- Nina is tricked into attending the bar mitzvah of a 13-year-old who has a major crush on her.
- 17. Where's Poppa? Mar 15, 2001
- Jack worries that Maya's new love-interest may be her illegitimate brother.
- 18. Erlene and Boo Mar 29, 2001
- Nina's visiting sister sparks jealousy when she woos the Blush staff.
- 19. Fanny Finch Apr 19, 2001
- Finch urges his mother to go out with heartbroken Jack; Elliott tries to help a photographer.
- 20. Sugar Momma Apr 26, 2001
- A romance novelist woos Finch; Nina criticizes a handicapped actor.
- 21. Maya Stops Thinking May 3, 2001
- Maya has a fling with a man who turns out to be the new creative consultant at Blush.
- 22. At Long Last Allie May 10, 2001
- Jack's ex-wife demands a position as a Blush columnist as part of their divorce settlement.