Season 5 · Episode 21 — Brotherly Love
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.
Season 5 episodes
E1Charlie Crawford is late for his first press conference as the new deputy mayor. He later runs into trouble trying to settle a tollbooth wo…
E2Charlie tries to get the mayor to a dentist before an important photo shoot. Caitlin hires a new male assistant only because he's attractiv…
E3Caitlin causes a misunderstanding when she believes that Charlie is taking a Spanish class to improve relations with the Latin American com…
E4Caitlin auditions for the job of co-host on ""Live with Regis."" Stuart and Paul work together supervising after bones are discovered under…
E5Caitlin 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…
E6Paul 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 hi…
E7Caitlin and Charlie fight the attention of Caitlin's new friend. Carter, Stuart and Paul compete for a trip to New Orleans with the mayor.
E8An overworked Charlie causes problems after beating the mayor at racquetball. Paul's annual request for a raise is approved by the mayor af…
E9Mike has been in Zimbabwe for three weeks, so Paul teaches Caitlin about celibacy. Stuart convinces Angie that he's a biker guy. War on une…
E10Paul struggles to find the best joke for the mayor's Christmas card. Carter convinces Caitlin to volunteer with him at a retirement communi…
E11In an attempt to get over Claudia, Paul decides to move into a college dorm. Caitlin tries dating, after ending her relationship with Mike-…
E12Caitlin sets the mayor up with her neighbor, Judith, who becomes way too much of an influence on the mayor. Carter helps Stuart prepare for…
E13Paul, Stuart and Carter rope reformed gambler Charlie into their poker night, and are responsible for his subsequent gambling bender. Caitl…
E14When a supermodel sues the mayor, Charlie hires his old college friend to defend him. Charlie finds himself torn between two friends after…
E15Carter 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…
E16Julia'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 an…
E17The mayor's daughter Meg returns and inspires Caitlin to be more spontaneous and free. Paul, Stuart and Carter give Charlie advice about co…
E18Stuart is hired to write a porno movie. Charlie and Caitlin compete for a donation from a wealthy male chauvinist. After Paul poses as the…
E19Charlie tries out for a minor league baseball team, trying to relive his high school glory days. Caitlin encourages the pitcher to go easy…
E20Caitlin falls hard for a rich, young, sexy philanthropist. The Mayor is threatened when Charlie temporarily takes over as acting Mayor, and…
E21Charlie attempts to interfere with Caitlin and Tim's burgeoning relationship. Meanwhile, Carter hires his sister to work at City Hall and w…
E22Charlie 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, C…
E23The 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,…