Charlie tries to get the mayor to a dentist before an important photo shoot. Caitlin hires a new male assistant only because he's attractive. Carter and Stuart deal with someone who keeps parking a bike in their parking space.

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.

Caitlin goes out of her way to prove that she's fun after a blind man won't date her because she's not. Charlie accidentally talks Claudia into becoming a nun; she leaves Paul. The mayor researches religion.

Paul convinces his mother that he is dating Caitlin, so she won't be upset that Claudia left him. Charlie tries to prove to Caitlin that his girlfriend isn't dumb. A quickly made balloon for the Thanksgiving parade goes awry in New York.

Caitlin and Charlie fight the attention of Caitlin's new friend. Carter, Stuart and Paul compete for a trip to New Orleans with the mayor.

An overworked Charlie causes problems after beating the mayor at racquetball. Paul's annual request for a raise is approved by the mayor after his loss of self esteem. Stuart hires an actor to go out with Carter.

Mike has been in Zimbabwe for three weeks, so Paul teaches Caitlin about celibacy. Stuart convinces Angie that he's a biker guy. War on unemployment forces the mayor to work at a burger joint.

Paul struggles to find the best joke for the mayor's Christmas card. Carter convinces Caitlin to volunteer with him at a retirement community. The mayor's attempt to be more involved in the office process goes awry.

In an attempt to get over Claudia, Paul decides to move into a college dorm. Caitlin tries dating, after ending her relationship with Mike--but doesn't have much luck. The Mayor builds an access ramp after he gets caught parking in a handicapped parking space.

Caitlin sets the mayor up with her neighbor, Judith, who becomes way too much of an influence on the mayor. Carter helps Stuart prepare for a million dollar shot at a Rangers' game. Paul thinks he's Canadian.

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.

When a supermodel sues the mayor, Charlie hires his old college friend to defend him. Charlie finds himself torn between two friends after Scott hits on Caitlin. Meanwhile, Paul and Stuart compete for the same woman.

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.

Julia's having a hard time dealing with her kiss with Charlie, so he asks her out. Their first date is a nightmare. Meanwhile, the mayor and his staff take the subway to prove that the mayor is in touch with the people. The train gets stuck in a tunnel, screwing up Charlie's plans for a second date. Meanwhile, Paul tells an exclusive cafe that Carter is Cuba Gooding Jr. to get reservations.

The mayor's daughter Meg returns and inspires Caitlin to be more spontaneous and free. Paul, Stuart and Carter give Charlie advice about compromising with Julia. This leads to Charlie deciding he's ready to commit, while Julia decides she's not.

Stuart is hired to write a porno movie. Charlie and Caitlin compete for a donation from a wealthy male chauvinist. After Paul poses as the Mayor's son for a golf tournament, he becomes confused when the Mayor actually begins paying attention to him.

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.

Caitlin falls hard for a rich, young, sexy philanthropist. The Mayor is threatened when Charlie temporarily takes over as acting Mayor, and Paul becomes addicted to Carter's nicotine gum.

Charlie attempts to interfere with Caitlin and Tim's burgeoning relationship. Meanwhile, Carter hires his sister to work at City Hall and will go to any length to avoid people discovering their connection.

Charlie and Caitlin fight as she plans to go to the Caribbean for a week with Tim on the night of a police ride-along. On the ride-along, Charlie is shot...by Paul. Charlie fakes the severity of his injury to get Caitlin's attention. Charlie and Caitlin almost kiss, but Tim interrupts. Meanwhile, Carter and Stuart worry that they bicker like an old married couple.

The Mayor hires Chad, an old prep school buddy who is now a bum. Charlie and Caitlin double date with Tim and Charlie's crazy ex. However, Tim dumps Caitlin, who calls Charlie to come over. They kiss; he freaks out and just wants to be friends, but reconsiders and shows up on her doorstep later. The mayor remembers why he and Chad didn't get along in the first place.