Mike shows up at Caitlin's to announce that he's met someone. Meanwhile, the mayor is dating a judge who's not yet divorced. Charlie suggests that the mayor break it off, but after getting some advice from Mike, he decides to let the mayor do what makes him happy. Charlie impresses Caitlin but Mike interrupts again to announce his engagement.

The mayor's approval ratings are going down, thanks to his relationship with the not-yet-divorced Judge Simmons. Charlie convinces the mayor to seek quiet time with Claire at a friend's house--only he didn't anticipate the mayor showing up at his. Paul hires a publicist to improve his image. After going to a friend's baby shower, Caitlin becomes obsessed with having a baby. Carter lets her watch Rags for a day, but he swallows Charlie's pager. Caitlin decides not to have a child, but apparently, Carter does.

Charlie discovers that Jennifer's ex is a woman. He becomes jealous when watching her be affectionate with Caitlin, something Caitlin dismisses until Jennifer kisses her on the lips. Claudia and Paul's divorce settlement may be affected by the mayor's bickering with Judge Claire.

Charlie endangers his relationship with Jennifer when he realizes that he loves his staff more than her. The Mayor decides to propose to Claire, but she says no because he's in the public eye and must be dishonest. This causes problems, because it's Election Day, and a truth-telling campaign by the Mayor could jeopardize his re-election.