Mike Flaherty unexpectedly visits from Washington, meets his replacement Charlie, and ruins Charlie's attempts at wooing Caitlin. Meanwhile, Randall begins dating Judge Claire Simmons, who is separated from her husband, but not divorced.
Randall tries to impress Claire by having a tree cut down, only to find out that the tree is an historic landmark. And Charlie tells it to a stranger, who turns out to be the campaign manager for Randall's opponent Julian Wheeler.
Charlie and Caitlin obtain damaging photos of Julian Wheeler in retaliation for him slamming Randall in campaign ads. Carter's coworkers help impress an adoption agency official and friend Michelle strikes up a friendship with Stuart.
Charlie sleeps with Julian Wheeler's campaign manager Jennifer Duncan. Caitlin and Paul both befriend Robin Jones, but Randall thinks Robin is only using Paul for sex. Randall's approval rating is up with young voters.
Caitlin's mother (played by Michelle Phillips) has been pressuring Caitlin to get married so she passes off Charlie as her boyfriend at her cousin's wedding. Paul is invited to a fashion show by a childhood friend (played by Rhea Durham).
The mayor's opposing candidate makes fitness a campaign issue but the opposition's wife (played by Elizabeth Mitchell) runs in his place after he has a heart attack. Charlie and Caitlin help each other out of bad dates.
On Election Day, the staff is nervous over the close race. Mayor Winston proposes to Claire (played by Farrah Fawcett) while Charlie continues his relationship with Jennifer (played by Denise Richards).
Randall's new girlfriend Christine is the receiver of his late mother's artificial heart. Caitlin dates an older man named Tom while Charlie dates Tom's daughter, and the four of them wind up in family counseling.
Carter's dog dies. The mayor looks into charitable foundations to make a donation. Meanwhile, Caitlin surprises Charlie on his birthday with a visit by his estranged con man father (played by Martin Sheen).
Randall asks Charlie to keep tabs on his niece Stephanie, who makes passes at him. Paul's latest gaff is of the romantic variety and takes place on a "Blind Date" TV show. Carter buys an expensive coat and Randall purchases a new Corvette.
Randall's insomnia is linked to Paul receiving a lucrative job offer from a senator. Carter joins the Big Brother program, but his visiting Little Brother Spencer winds up spending time with Caitlin and a very uncomfortable Charlie.
Paul feels depressed when his divorce is finalized, so Carter feigns heterosexuality to help him play the dating game. Charlie and Caitlin have a flashback to their first meeting - in 1988 during a political event for Michael Dukakis.
At a mayors' conference, Caitlin feels awkward because Charlie once had an affair with the organizer, so Caitlin tries to make Charlie jealous. Randall renews his long-standing professional rivalry with Mayor Stone Taylor of Los Angeles.