Stacy's staying with Carter and Stuart while her apartment is fumigated. Her partying cramps their style. Trying to outdo NASCAR driver Jeff Gordon and NBA player Jayson Williams, the Mayor promises his kidney to a young boy. Unfortunately, his doesn't match--but Mike's does. Meanwhile, Mike's playing the jealousy game with Nikki and promises to donate his kidney to the boy in hopes that she'll break up with Arthur for him. But when she offers him a chance to speak up about his feelings, he's anesthetized for his surgery and can't say anything.

The staff pesters Nikki for details about her sex life with Mike. James asks Mike to invest his life savings in an Internet company, but when Mike holds off on investing, the stock goes up several points, and Mike must find a way to make the money back. Meanwhile, the mayor has an action figure made of himself but unfortunately, they're all anatomically correct.

Mike tries to convince Nikki that nothing is going on between himself and Heidi Klum. The mayor doesn't understand that Janelle wants to break up with him. Janelle gets Mike to do it for her, but Nikki overhears Mike talking to Carter about it and thinks that Mike is going to break up with her. After Rags poops in his shoe, Stuart gives him to Heidi. Nikki breaks up with Mike. The next day, there is tension in the office. Carter tells Nikki the truth. She goes to Mike's apartment where Mike is hung over. As he goes back into his room to put on his pants, Heidi sits up in his bed...

Mike invites Caitlin to his Christmas party as his only guest but his plans at romance are spoiled when she arrives with a date. Paul finds John McEnroe's headband in the City Hall clothing drive box. James finds a second job as a suicide hotline operator. Stuart installs a chin-up bar in the mayor's office, which the mayor promptly injures himself on.

The mayor prepares for a three-day trip across New York on his new campaign bus. Paul and James grow mustaches when they think that Carter's gets him the best assignments. Nikki becomes a female version of Stuart when she consults him for dating advice. After Mike discovers that Trevor has asked Caitlin to marry him again, he accidentally hits him with the bus. Mike and Caitlin kiss but their session is interrupted when Mike reveals he was deliberately aiming for Trevor.

Caitlin prepares to marry Trevor and elopes to Paris, where Mike follows and reveals that he loves her. James becomes angered with the mayor when he receives an undeserved war award. Stuart asks Nikki to pose for a ""charity"" swimsuit calendar.

Caitlin causes a misunderstanding when she believes that Charlie is taking a Spanish class to improve relations with the Latin American community. Paul and the mayor struggle to create office water-cooler talk. Stuart becomes jealous of the time Carter has been spending with Caitlin.

Paul, Stuart and Carter rope reformed gambler Charlie into their poker night, and are responsible for his subsequent gambling bender. Caitlin tries to teach the mayor to be more self-sufficient.

Carter discovers an old love letter written by Stuart. He decides to set Stuart up with the addressee of the letter, a woman who turns out to be Stuart's ex-wife. The woman quickly manages to set a whipped Stuart into his old rut. Meanwhile, Caitlin hires an image consultant when the mayor's approval ratings go down. The consultant discovers that the mayor has a problem with women, causing Charlie to make himself over. And also, Paul worries that he's unrecognizable.

Charlie tries out for a minor league baseball team, trying to relive his high school glory days. Caitlin encourages the pitcher to go easy on him. The mayor receives a death threat so he gets a bodyguard. After discovering that his job requires him to come into contact with the mayor so often, Paul receives a bodyguard also. Rags spends a day at the office.

The mayor hires a political strategist to act as his campaign consultant. The consultant, Robin, is a bit of a psychic, predicting that a date of Charlie's will result in disaster, so Caitlin rushes to save him. As Stuart becomes more involved with Michelle, she tries to determine whether she is pregnant with Carter's artificially inseminated child yet. Stuart realizes that he may be the father after revealing that he forgot protection one night. However, Michelle discovers that she's not pregnant.

Charlie endangers his relationship with Jennifer when he realizes that he loves his staff more than her. The Mayor decides to propose to Claire, but she says no because he's in the public eye and must be dishonest. This causes problems, because it's Election Day, and a truth-telling campaign by the Mayor could jeopardize his re-election.

Caitlin takes a trip down memory lane and realizes that she and Charlie met years before and that he was the reason why she lost what might have been the best relationship of her life. Flashback to a preppy and conservative Caitlin and a cool, life-of-the-party Charlie at an old college bash. The flashback makes Caitlin realize that her current boyfriend, Tom, might not be right for her, and she ends up kissing Charlie! Meanwhile, the Mayor bartends at a fundraiser at which Paul is trying to pick up a woman, and the woman's friend has fallen for Carter, who is gay.