Lisa's (Maura Tierney) new assistant (guest star Tiffani-Amber Thiessen) is attracted to Dave (Dave Foley) Jimmy (Stephen Root) turns the men's room into a cigar lounge. With Joe Rogan, Andy Dick and Jon Lovitz.
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Paul's parents give Paul and Jamie a trip to the Caribbean. The only problem is, to use it they have to pretend to be Paul's parents, and it proves very difficult.
Paul is heading to Canada but Lisa has accidentally taken Jamie's purse by mistake which contains Paul's passport, so they run around town to find her.
Maya's past behavior makes it hard for Jack to get Hannah enrolled in Maya's old school Elliot and Nina discover they share a fascination with the same blues singer/songwriter.
A Woody Allen impersonator (Ed Crasnick) is drawn to Maya after she pens a favorable article about the filmmaker Jack loses his sight for a day.
Maya is upset when her father gives tickets to a Royal Shakespeare Company production and a flight to London to Elliott and Nina.
Despite warnings from Elliott, Finch falls for the beautiful Nikki Elston, and the staff must intervene.
Malcolm and Eddie switch places after betting each other that one could run the other's business better.
Malcolm hires a new chef and lands in hot water after purchasing stolen lobsters Eddie and Nicolette's affair comes to a crossroads.
Dave tries to convince the staffers they have a shot at winning at a broadcast awards ceremony hosted by Bob Costas.
Due to their lack of holiday spirit, Jimmy decides not to invite any of the WNYX employees to his annual Halloween bash.
Beth (Vicki Lewis) orders a video arcade game for the office, much to the delight of Mr. James and Dave (Stephen Root, Dave Foley).
Paul agrees to go with Jamie on a blind date with Nick and Fran. He then discovers that Mark, Fran's ex-husband, is back in town and working in their local restaurant.
Jamie is nervous about going back to college, so Paul does his best to encourage her. Paul panics when he realizes that he forgot to mail in her registration, so he rushes to the college to put things right before she gets there.
Jamie and Paul go out to dinner with both sets of parents. Their mothers begin to argue over the last scampi, but Jamie and Paul refuse to take sides. Lisa plays one set of parents against the other.
Blair has to compete for her boyfriend's attention when a movie star enrolls at Langley College.
Blair can't deal with Jo's increasing popularity.
Natalie's father dies unexpectedly.
Ann finds herself in her most serious romantic involvement since her divorce.
A teacher's critical remarks plunge Julie into a deep depression.
The real murderer of Peter Campbell is revealed Chester gets put in the same cell as Dutch.
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