About the Show

The Gambler - 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.

In the Company of Dudes - 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.

The Image Maker - 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 hiresan 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.

Trainstopping - 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.