Mike Flaherty's replacement Charlie Crawford reports to work. Caitlin's efforts to avert a toll booth workers' strike hit a roadblock when the woman with whom she's negotiating turns out to be an ex-girlfriend of Charlie's.

Randall needs dental work, but his long-time dentist drops dead during the procedure. Charlie interviews personal assistants until Caitlin hires one based on looks. Stuart goads Carter into aggression when Carter's parking space is stolen.

Charlie never graduated school due to a missed Spanish final exam, and Caitlin does more harm than good in trying to help. Randall installs a water cooler. Stuart is jealous of Carter's friendship with Caitlin and uses Rags to get even.

Caitlin makes an appearance on Regis Philbin's live television show. Mayor Winston takes a vacation - well, sort of. Paul and Stuart mediate a dispute between paleontologists and construction workers.

An abrasive blind man finds Caitlin dull, spurns her, and causes her to try to improve her personality. In need of a religion refresher, Randall and Charlie accidentally wreak havoc on Claudia's religious education class and her future.

The staff tries to appease Native Americans by having an appropriate float in the Thanksgiving parade, but things go awry. Paul's visiting mother doesn't know that Claudia has left him and he is afraid to tell her.

Charlie's one-night stand with Caitlin's yoga class buddy Samantha doesn't go the way he planned. Paul, Stuart, and Carter compete to join Randall on a trip to New Orleans.

Charlie plays racquetball with Mayor Winston, beats him in a match, and crushes his ego. Paul campaigns to get a raise. Stuart hires an actor to date Carter.

Randall, Carter, and Charlie spend time working in a fast-food restaurant. Stuart tries to impress Angie by feigning expertise on motorcycling. Paul teaches Caitlin the rigors of celibacy.

Confiscated toys may become part of a photo op for Randall, who undermines Charlie's staff meetings. Carter persuades Caitlin to volunteer with him in a retirement home. Paul seeks jokes to enliven the City Hall holiday greeting card.

Paul moves into a college dorm. Charlie sets up Caitlin on a blind date with a bumbling optimist. Randall parks in a handicapped spot and makes amends by having a ramp installed in City Hall.

Much to Charlie's disdain, Mayor Winston's new girlfriend Judith usurps Charlie's authority by involving herself in policy issues at City Hall. Carter and Stuart brawl during a hockey game.

Paul, Carter, and Stuart goad Charlie into playing poker with them, not knowing that he is a reformed gambler. Caitlin helps Randall search for a new housekeeper, then vetoes every applicant.

Charlie calls a college buddy to defend Randall in a lawsuit after he ruins a model's coiffure at a charity fashion show, but the man has eyes for Caitlin. Carter coaches Paul on wooing an attractive new hire before Stuart goes after her.

Caitlin hires an image consultant to determine why Mayor Winston's approval rating with women has plummeted. Stuart's overbearing ex-wife comes back into his life, courtesy of Carter's bungled attempt at matchmaking.

Charlie gets trapped in a stalled train before his date with a woman he's desperate to impress. Carter's weird neighbor Kurt hits on him, and Paul helps by getting Carter reservations at a posh restaurant.

Randall's visiting daughter Meg decides to become a free spirit by dropping out of law school and moving south with her loser boyfriend. Charlie blows off a date with Julia to attend a sporting event with Stuart, Carter, and Paul.

Caitlin and Charlie vie for an important account. Randall bonds with Paul during a father / son golf tournament. Carter helps Stuart write the script for a pornographic movie during working hours.

Charlie fulfills a dream of playing minor league baseball, but Caitlin bribes the pitcher into going easy on him so he'll return to work. Randall receives a death threat and beefs up security, which Paul exploits to get revenge on Stuart.

When his wife's book turns out a great laugh, but at the expense of his male pride, mayor Winston gets so depressed he is unfit to appear in public and must be replaced by his top aids. Superrich most eligible bachelor Tim Connelly is very pleased he thus spends an evening with Caitlin, who is attracted to him, except his embarrassingly boyish obsession with a SciFi series, which even means their next date is a fan convention. Charlie has a ball getting mayoral attention. Stuart enjoys taunting his colleagues by helping stingy Paul steal Carter's nicotine chewing gum, so they'll both be tortured by its addictive properties.

Carter helps his sister get a job at City Hall, but lets Stuart and Paul think she is his lover. Randall thinks he looks like Charlton Heston. Charlie and Tim compete for Caitlin's affections.

When Tim doesn't just propose another evening with Caitlin but a trip to St.Barts, she has her first real row with Charlie. After the press finds out the mayors limousine was carjacked with him, Paul and Charlie in it, PR demands they spend a night with an officer on patrol in a police car, while Stuart and Carter ride a police horse together; Charlie gets shot -accidentally as a video camera proves, but by...- which brings Caitlin running back to him, only to find out it's just a superficial wound...

Caitlin finds that Charlie lied, and pulls a prank on him. Charlie dates a mentally unstable woman so that he seems unavailable. Randall offers a job to a high school classmate, now a hobo, to make amends for ruining the man's life.

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.

Mike's engagement falls through, so he immerses himself in his old job at City Hall, aggravating Charlie. Randall prepares for a charity fund raiser.

When Randall's approval rating drops because of his relationship with Claire, Charlie advises him to be discreet; so Randall and Claire freeload on Charlie. Paul hires a publicist.

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.

Randall's campaign consultant Robin has psychic gifts, which predict impending disaster for Charlie. Stuart dates the surrogate mother of Carter's child and realizes that he himself may be the father.

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.

Charlie and Caitlin have lunch with Jennifer, who makes a startling confession. A cooling between Randall and Judge Claire Simmons puts Paul's divorce settlement from Claudia in jeopardy.

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 delegates Charlie to decide which staff member will move into a beautiful new office. Caitlin tries to find out what the City Hall Santa Claus looks like before she dates him.

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.

Charlie is exhausted from keeping up with his much-younger girlfriend Tracy. Gay art dealer Martin Davis invites Randall, Carter, and Stuart to a fund raiser, where Martin and Carter might hit it off.

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.

A therapist helps Caitlin sort out her feelings for both Tom Crandall and Charlie. Carter tries to help Paul to prepare for an appearance on Larry Elder's call-in radio program.

Stuart extends his vacation, so a temporary replacement is hired and performs better than Stuart does. After much thought, Caitlin breaks off her relationship with Tom Crandall.

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.

Randall tries to please visiting Governor Riley. Charlie and Caitlin struggle to keep their affair secret and Stuart senses there's something strange in the office. Carter is getting a foster child.

Randall's visiting daughter Meg decides to become a free spirit by dropping out of law school and moving south with her loser boyfriend. Charlie blows off a date with Julia to attend a sporting event with Stuart, Carter, and Paul.

Charlie gets trapped in a stalled train before his date with a woman he's desperate to impress. Carter's weird neighbor Kurt hits on him, and Paul helps by getting Carter reservations at a posh restaurant.

Stuart extends his vacation, so a temporary replacement is hired and performs better than Stuart does. After much thought, Caitlin breaks off her relationship with Tom Crandall.

Paul, Carter, and Stuart goad Charlie into playing poker with them, not knowing that he is a reformed gambler. Caitlin helps Randall search for a new housekeeper, then vetoes every applicant.

Charlie fulfills a dream of playing minor league baseball, but Caitlin bribes the pitcher into going easy on him so he'll return to work. Randall receives a death threat and beefs up security, which Paul exploits to get revenge on Stuart.

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.

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).

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 finds that Charlie lied, and pulls a prank on him. Charlie dates a mentally unstable woman so that he seems unavailable. Randall offers a job to a high school classmate, now a hobo, to make amends for ruining the man's life.

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.