Farm-fed Jane Sokol is sent to New York to manage Chelsea Steven's magazine and television show after it is bought by the Ferber Corporation, but is totally thrown by her dealings with the eccentric gourmet --- who immediately goes through Jane's purse to learn about her and interferes in her relationship with her ex-fiance.
After the apartment for her magazine makeover becomes unavailable, Chelsea convinces a reluctant Jane to allow her apartment to be used -- insisting that Jane stay with her during the renovation. Jane, however, is not prepared for the extreme eccentricities of her benefactor -- who proves to be a drill sergeant: waking Jane at the crack of dawn to pluck chickens, shear sheep, plow fields and perform endless farmyard chores. Jane thinks things couldn't get any weirder until Chelsea reveals her biggest secret -- Chelseatown, a miniature town in the attic that Chelsea has designed in her own honor.
The incompetence of Chelsea's assistant Terry comes to a head after he sends Chelsea to the wrong address for lunch -- resulting in a near mugging. Having only hired Terry as a favor to a friend -- his aunt, Chelsea uses the friend's coma as an opportunity to have Jane fire him. After several failed attempts, Jane is finally able to convince Terry that he is no longer wanted and hires Chelsea a new assistant who is organized and efficient -- not to mention gorgeous, but pangs of guilt send Chelsea chasing after Terry.
When Jane tells Chelsea that there is no budget for her new super-equipped van, Chelsea's arrogant lawyer Bobby convinces her to cut the staff's holiday bonuses to free up the funds. But after Jane offers the alternative solution of dropping Bobby from retainer and putting him on his hourly rate, Bobby retaliates by playing a series of practical jokes on her. Jane refuses to stoop to his level by responding to his tactics, until he finally pushes her too far -- and Jane proves that she can out-prank the prankster.
A heartbroken Chelsea thinks her ex-husband is pining for her 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 to break the news of his homosexuality to his elderly parents when they visit from England, while the staff notices that his father is quite a flamer himself.
Wanting to make a good impression on her visiting boss, Jane is devastated when the personality clash between Mr. Ferber and Chelsea becomes an all-out scene in a restaurant -- and later a one night tryst -- which results in the infatuated Mr. Ferber leaving his wife and contemplating suicide.
After being labeled frivolous and empty-headed in a magazine article, Chelsea jumps at a chance to boost her public image by participating in a talk show to discuss current events in the Middle East. Realizing that Chelsea knows absolutely nothing about politics and that the show's producers intended her to humiliate herself on national television, Jane volunteers to tutor her on the show's discussion topic. Chelsea bones up all night on the topic of the Middle East, but is completely unprepared when she finds out that Terry forgot to give her the message that the topic had been changed to NAFTA.
Jane decides to surprise Chelsea by inviting her childhood idol, world-famous TV gourmet Gloria Utley, to appear alongside her on Live with Regis & Kathie Lee. Unaware that Gloria is now a burned-out boozer, no one is prepared for a drunken display by the loony Gloria on live television -- especially Chelsea.
Jane meets a charming soap opera star, Dax, and begins a whirlwind romance, ignoring Chelsea's warnings that he is too vain and self-absorbed. Later, when Jane tries to wash her hands of the bubble-headed soap star, Chelsea devises a scheme to free her from the needy actor by stealing a tragic plot straight from the soap operas (which she has started watching in preparation for her guest appearance). Meanwhile Terry is bullied by an abusive deliveryman.
Chelsea covets a valuable Chinese dinner plate of Jane's, but after Jane refuses to part with it for sentimental reasons, Chelsea uses an office mix-up to get her hands on it. Unfortunately, she accidentally breaks it and has to replace it with one from her own prized collection -- despite having discovered that Jane's was a fake.
Jane convinces Chelsea to accept a dinner invitation from an old friend -- her first date since her divorce -- but is shocked when Chelsea announces her sudden engagement to the man. Jane urges Chelsea to use common sense and not rush into marriage too quickly -- but Chelsea is having too much fun planning an extremely lavish, extravagant wedding. Meanwhile, Chelsea puts a number of her society guests, including Carol Channing, to work creating elaborate decorations for her nuptials.
In an effort to win recognition as a humanitarian, Chelsea agrees to host a garden party for a large charitable foundation in the fight against substance abuse. Unfortunately, she buys fresh produce from a roadside vendor and mistakenly serves ""magic mushrooms"" at the party -- leaving her high society guests somewhat dazed and uninhibited. Meanwhile, Terry finds a wing nut in a candy bar, prompting Trudy to embellish the facts in a complaint letter to the manufacturer.
In the final episode, which was never broadcast on CBS, Chelsea was doing a video shoot in her home for her new TV special. When an obnoxious neighbor's noisy pet pig, Alfonso, becomes overbearing on the audio track, Chelsea threatens Mrs. Oliver to shut the pig up. Later that day, Jane accidentally backs her car up over Alfonso and kills him, and at the advice of Trudy and Mr. John, decides not to say anything and let Chelsea take the blame. So when Chelsea gets sued by Mrs. Oliver for $50,000 in what the press dubs ""Porky Gate,"" Jane has decide whether or not to remain silent.