Caitlin tries to sabotage Mike's date with her visiting sister Catherine. Stuart joins the other staffers in taking an interest in art. Paul is upset to learn that Carter makes more money than Paul does, so Paul starts acting immaturely about the matter.

In order to improve Mayor Winston's political advertisements, Mike hires a British director named Trevor who turns out to be more than just an old friend to Caitlin. James obsesses over whether or not he is gay. Paul uses makeup to cover a skin rash.