Крученый город, 5-й сезон

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 and the Mayor hires an old prep school buddy who is now a bum.