As the cast and crew of TGS with Tracy Jordan returns for a new season, Liz is excited to see Jack again. However, her excitement quickly fades as Jack insists that Liz is still not over Floyd. Meanwhile, Jerry Seinfeld shows up at Jack's office in an upset mood after Jack announces his newest plan. Finally, Kenneth becomes Tracy's office wife when Tracy separates from his wife and Jenna returns to set a whole lot heavier now that she has been involved in Mystic Pizza: The Musical!.

When Jack discovers that his boss is retiring, he decides to get in the competition for his position. Meanwhile, Jenna begins to enjoy her fame for being fat and along with Jack encourages Liz to get her act together. Finally, Kenneth makes it his mission to get Tracy and Angie back together.

Jack hires his own private investigator to lead GE in the wrong direction so that they will not be able to find any dirt on him that might put him in a compromising position. However, when he is asked to give up his cookie jar collection, Jack finds the task too much of a challenge. Meanwhile, Angie announces that she will follow Tracy at all times to keep him in line, which Liz believes to be good until she covers for Tracy and gets on Angie's bad side. Finally, Jenna starts to worry once she starts to lose all the weight she gained over the summer and her popularity begins to hang on the line.

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.