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.

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.