Tracy wants Josh to be fired, because he doesn't like Josh's impression of him. Liz tells Josh to stop making the impression, but he doesn't. Cerie is engaged to a guy whom she only has known for 3 months and Liz kind of worries that Cerie is making a mistake to marry. After talking to Cerie about marriage and kids, Liz can hear her biological clock ticking. She tells Jenna about her concerns and Jenna tells the complete staff. Jack is very stressed out, especially because of his mother, who constantly calls him from her retirement home.
Jenna and Liz meet two people working at NBC whom they call the head and the hair, because they don't know their names. Jenny sends Liz to ask the head for a date, but Liz ends up with the hair. Just for one day, Jack works for Kenneth and gets to know some of the uncomfortable work Kenneth has to go trough. Tracy realizes that his autobiography is due the next day and involves a main part of the staff in the writing process.
Jack asks Liz to accompany him to a very classy event, which leads to the assumption that this will be a date. Jack first tells her it is not a date until they meet his ex-wife at the party and Jack introduces Liz as his girlfriend. Jenna sneaks herself into the party, because she wants to meet the Austrian Highness, whose birthday is celebrated at the party. Tracy uses the NBC office as a party spot and invites some female dancers over. One of the dancers tries to seduce Pete into cheating on his wife and he even thinks about doing so. Kenneth tries to stop him.
Liz makes the staff work on Valentine's Day all night long. While Liz gets flowers and she doesn't know who send them to her, Pete forgets about the Valentine's Day, which is also his wife's birthday. Jack meets with Bianca to make their divorce final. To celebrate that he is divorced, Jack goes with Tracy into a bar, but Tracy has to leave because he wants to spend time with his wife. Jenna has got the feeling that Frank doesn't like her, which turns out to be true when he tells her so. Meanwhile, the staff tries to talk Kenneth into hooking up with Cerie.
Kenneth becomes part of Tracy's entourage. And, while Kenneth treats Tracy honestly, it turns out that other members of Tracy's entourage have let him win computer and basketball games and even laugh about his jokes, when they are not funny, just to please him. Jenna is voted as one of the funniest women by a magazine and when giving an interview for the magazine gets mis-quoted about the American army troops. This gives her a bad public image. To correct this, she wants to give another interview but it seems as if she has no idea what she is talking about. Jack wants...
Liz dates an African American man called Steven and when they don't hit it off, he accuses her of racism. Jack tries to mend a feud between Tracy Jordan and rap producer Ridikolus by having the former present the Source awards and the latter endorse his Donaghy wine.
Eddie, Jack's brother, comes for a visit, who tells him that their father died. It turns out that Jack hasn't seen his father in 17 years and that Eddie took care of him for the rest of his life and is now broke and his now to live in the YMCA. While their first meeting ended in a fight, it is now time for them to reconcile. Liz is supposed to fire 10% of her staff and, as everyone finds out, the staff tries to please her as much as they can to not get fired. During aerobics Liz meets the guy who accidentally send her flowers on Valentine's Day and his girlfriend. ...
After the fireworks-disaster Jack is taken away the microwave department by Don Geiss. Geiss also talks to Tracy, who tells him about his movie project "Jefferson" in which Tracy wants to play Thomas Jefferson, who turned out to be one of his ancestors. When Geiss turns the ideas down, Tracy plans to shoot an own "Jefferson" promotion on his own to convince Geiss that the movie is a great idea. Liz is very happy with Floyd and Jack wants to meet him. So, Jack, Floyd and Liz are having dinner together, but Jack is very sad about being taken away the microwaves and ...
Tracy goes AWOL before the final show to avoid the "Black Crusaders," but Kenneth reveals that he's actually staying with his cousin. Meanwhile, the pressure of his imminent wedding and a visit by his mother lands Jack in the hospital.
An angry Jerry Seinfeld goes to 30 Rock to confront Jack after he learns that Jack plans to digitally insert him into every current NBC program. Meanwhile, Liz buys a wedding dress, even though her marriage prospects are slim.
Jack is in the running for the G.E. chairmanship and hires a private eye to dig up any dirty secrets. The P.I. exposes Jack's enormous cookie jar collection (he was collector of the year under the pseudonym Victor Nightingale) and advises him to get rid of it. Jenna is more successful than ever now that she's overweight, but panics when it turns out her happiness is making her lose weight.
Liz befriends a female comedy writer from the 1960s who was one of her idols, until she realizes how pathetic the woman's life is now. Meanwhile, Jack has to find a way to talk Tracy out of taking up dog fighting.
Jack has a one night stand with a Democrat who is campaigning against one of NBC's sister companies, Liz suspects her neighbor is a terrorist, and Kenneth tries to raise money to buy Jack a pair of pants.
C.C. wants to go public with her relationship with Jack after talking with Liz, Toofer and Frank take their feud to dangerous levels, and Jenna becomes jealous because she thinks Tracy is getting more attention.
Jack gets attached to Liz's nurturing parents because they provide the love and support he never got from his mom. The staffers get ready for their raunchy holiday party, but Kenneth changes their plans at the last minute.