Roy is depressed over his recent breakup with his girlfriend. Jen applies to be the company's Entertainment Manager, despite not caring that the position was originally done by a man who would act as a pimp and take clients to seedy places. Roy likens Jen's job to that of Fredo from The Godfather. Douglas tries to have a feminist committee take back the "Shithead of the Year" award they gave him. Following a disappointing visit with the clients to see The Vagina Monologues, Jen turns to Moss and Roy for ideas. Moss, who has been devising his own Dungeons & Dragons-styled role-playing game, invites Jen's clients and Roy for a session.