Caitlin tries to sabotage Mike's date with her visiting sister Catherine. Stuart joins the other staffers in taking an interest in art. Paul is upset to learn that Carter makes more money than Paul does, so Paul starts acting immaturely about the matter.
Paul's raffle ticket glitch results in dozens of winners. James gets braces at the same time that the new mail girl finds him attractive. Stuart and Carter blackmail Caitlin in order to get out of doing her busy work for her.
In order to improve Mayor Winston's political advertisements, Mike hires a British director named Trevor who turns out to be more than just an old friend to Caitlin. James obsesses over whether or not he is gay. Paul uses makeup to cover a skin rash.
Mike hires New York's oldest living voter, a 107-year-old woman, for a job. Caitlin's romance with Trevor upsets him. Paul muscles in on James' Hey Guy. Carter accuses a landlord of discriminating against gays.
Carter's new boyfriend Alex may be coming on to Mike. Paul tries to impress a reporter from his hometown until Randall upstages him. A Good Samaritan contest brings out five finalists. Stu plays a fat neck gag on James.
Angry farmers fight Randall's land proposal, and their leader turns out to be an ex-rival of James, who may be able to save the day. Deidre had a fling with Paul years ago. Carter disapproves of Randall spending time with a rap singer.
Randall seems unaffected by his cold father's death and rides an emotional roller coaster; Paul uses the opportunity to kiss up to him. Staffers use Paul's Magic 8 ball to make simple decisions. Is Caitlin attracted to James?
Romantic sparks fly between Mike and Caitlin during Mayor Winston's listening tour. Carter tells Nikkie to be more aggressive toward the men she wants in her life. James and Paul decide that Carter is more successful than they are, so they try to duplicate his success by emulating his physical characteristics.
Mike continues his pursuit of Caitlin, despite her engagement to remarry Trevor. Stuart disrupts Carter's hunger strike against an environmental polluter. Randall, Paul, and James try to do maintenance work in the office.
Mike follows Caitlin to Paris in order to break up her engagement to Trevor. James preps Randall to receive an award that he may not have earned. Stuart asks Nikki to pose for a calendar so that he can donate proceeds to charity.
Mike abstains from sex for a week to prove that his feelings for Caitlin aren't just physical, and Caitlin doubts he can do it. Randall uses Carter's dog Rags to project an animal-friendly image to animal rights activists.
Muckraking reporter Wayne Sheridan wants to connect Randall's administration to organized crime. Several staffers make this easy, including Randall and Nikki. Randall gives a sanitation contract to a mobster, whom Nikki is dating.
When Sheridan goes public about the Winston administration's links to organized crime, Mike decides to take the fall and save everyone else. He submits his resignation, leading everyone to drown their sorrows and say their goodbyes.
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.
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.
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.