Liz meets her longtime idol, Rosemary Howard, and invites her to be a guest writer on "TGS with Tracy Jordan". However, Rosemary's ideas turn out to be too much for the show, prompting Jack to pressure Liz into firing her. Meanwhile, Jack takes Tracy to a therapist to explain to him why he must do the opposite of what he is told, and Jenna ruins Kenneth's page jacket, causing him to compete in a page-off to keep his job.

In the second season finale, Jack moves on to a new job involving politics in Washington, but the position is not quite what he anticipated. Meanwhile, Liz suffers a pregnancy scare, Kenneth confronts rival page Donny when applying for a summer job, and Tracy works on his latest invention.