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.

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.

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 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 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.

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.

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.

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 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.

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.

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 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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.