It's Valentine's Day, and the TGS crew is celebrating by pulling an all nighter to put together a new episode. While Pete completely forgets the holiday, Kenneth and Cerie may be starting an office romance. Meanwhile, Liz wonders if Dennis is back in her life after she receives flowers from a secret admirer and newly divorced Jack wants to party with Tracy, who for once wants to spend a night alone with his wife instead.

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.

Amid a health scare that sees him growing close to his mother's nurse, Jack helps Tracy and his wife Angie develop a "post-nup" and gets Jenna an audition to play Janis Joplin. Jenna thinks Liz is only attracted to a little person because she wants a child.

Jack's biological father's health hangs in the balance as the pair start to build a relationship. Liz draws some attention as a relationship expert, despite her own many failed relationships, after an appearance on a talk show. Tracy is invited to speak at his old high school and Kenneth helps him overcome some embarrassing memories from those years.

The tables are turned when production begins on Liz’s new talk show, “Dealbreakers,” and she experiences what its like to walk a mile in Jenna’s shoes. Jack, dealing with pressure from Devin, calculates to make “Dealbreakers” a success. Meanwhile, Tracy takes on the ultimate Hollywood challenge in order to prove his commitment to his wife. Everyone pitches in to help Tracy reach his goal including Kenneth, Dotcom and Grizz.

Liz uses her newfound confidence to solve Pete's problem with a difficult editor (Paul Giamatti); Jack tries to cheat mortality; Tracy vows to be present when his wife gives birth.

Budget cuts at the company impact the "TGS" gang. Elsewhere, Liz's New Year's resolution adds a potential snarl to Jack's wedding; Jenna and Danny share a dressing room; and a health scare hits Tracy.

A reality TV series trails Tracy, which Liz tries to exploit for her own gain. Jack does his own exploiting: He attempts to make a fast buck off natural-disaster telethons. And Lutz sets out to increase his worth in the event of an apocalypse.

Angie's reality show visits "TGS", resulting in a red-faced situation for Jack, Jenna pining for attention, and Liz leading a scheme to lure Tracy back from Africa. Meanwhile, Frank reconnects with a lost love.

Angie brings "Queen of Jordan'' back to TGS. News about Avery forces Jack to confront his feelings for her mother, and Liz finds herself in a feud.