Randall's insomnia is linked to Paul receiving a lucrative job offer from a senator. Carter joins the Big Brother program, but his visiting Little Brother Spencer winds up spending time with Caitlin and a very uncomfortable Charlie.

Paul feels depressed when his divorce is finalized, so Carter feigns heterosexuality to help him play the dating game. Charlie and Caitlin have a flashback to their first meeting - in 1988 during a political event for Michael Dukakis.