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Jane Sokol is sent to New York to manage Chelsea Stevens' magazine and TV show after it is bought by the Ferber Corporation, but she's totally thrown by her dealings with Chelsea, who goes through her purse and meddles in her relationship with her ex-fiance.
When Chelsea decides to redecorate Jane's apartment for a magazine makeover, she convinces a reluctant Jane to stay with her during the renovation; Jane discovers how eccentric Chelsea really is when she reveals her biggest secret – Chelseatown, a miniature town she designed in her attic.
Jane wants to make a good impression on her visiting boss, but she is horrified by the personality clash between Chelsea and the condescending Mr. Ferber who has become hung up on Chelsea after a one-night stand.
Jane surprises Chelsea by inviting her childhood idol, world famous gourmet Gloria Utley , to appear alongside her on Live with Regis & Kathie Lee – unaware that Gloria is now a burned-out boozer.
After being labeled frivolous and empty-headed in a magazine article, Chelsea jumps at the chance to boost her public image by participating in a Politically Incorrect-style talk show to discuss current events in the Middle East.
No longer able to deal with the incompetence of her assistant Terry, Chelsea asks Jane to fire him – which winds up being easier said than done; meanwhile Trudy and Mr. John fawn over Terry's replacement, Matthew.
Chelsea incites an office rivalry between Jane and her arrogant lawyer Bobby in an effort to cut costs so she can buy an expensive super-equipped van; When Jane cuts Bobby's salary to provide the money for the vehicle, Bobby retaliates by playing a series of practical jokes on her.
Chelsea becomes consumed with getting her hands on Jane's valuable Chinese dinner plate, but when Jane refuses to part with it for sentimental reasons, Chelsea uses an office mix-up to get her hands on it; meanwhile, Trudy dates a guy who seems too good to be true.
Jane convinces Chelsea to accept a dinner invitation from an old friend, Jeff – her first date since her divorce – but is shocked when Chelsea announces her sudden engagement to the man.
Jane begins dating charming soap opera star Dax Chandler, ignoring Chelsea's warnings that he's too vain and self-absorbed; meanwhile, Terry is bullied by a creepy delivery man and Chelsea finds herself addicted to soap operas.
Chelsea thinks her ex-husband Grant wants her back when she and Jane run into him at a charity dinner with his latest girlfriend – who is Chelsea's spitting image; meanwhile, Mr. John is forced by his lover to tell his aged parents that he's gay.
In an effort to win recognition as a humanitarian, Chelsea agrees to host a garden party for a charitable foundation in the fight against substance abuse; unfortunately, she buys fresh produce from a roadside vendor and mistakenly serves psychedelic mushrooms to her guests. Meanwhile, Terry finds a wingnut in his candy bar, so Trudy writes a letter of complaint that lands them both in hot water.
Chelsea is blamed for killing the pet pig of her obnoxious neighbor Mrs. Oliver, which in fact was accidentally run over by the last person anyone would suspect: Jane.
