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.
Jack asks Liz to deal with a group of German TV execs so he can spend more time with C.C. but Liz has fallen in love with a piece of real estate. Tracy buys a cappuccino machine and gets Kenneth addicted to caffeine.
While the entire cast and crew is obsessed with watching the season finale of MILF Island, Liz tries to keep Jack from knowing that she is the person who made negative comments about him to a newspaper journalist.
Jack asks Liz to get her ex-boyfriend Dennis for the show after he becomes a hero for saving someone at a subway station, and tries to get Tracy to become an African-American spokesman for the Republican party.
Liz has a positive pregnancy test, and thinks that Dennis is the father. Meanwhile, Jack regrets taking the Homeland Security position, Tracy finishes his pornographic video game, and Kenneth tries to get a job at The Olympics.