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.
Don Geiss is prepared to name Jack as his replacement instead of his future son-in-law, and Jack is ready to name Liz as his replacement. Tracy tries to create a pornographic video game.
Jack's career at GE is on the line with Don Geiss in a coma, one of Liz's old flames comes back to town, and the guys confront the Teamsters on their sandwich day to get an extra sandwich for Liz.
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.
Jack comes back to GE, and is willing to do anything to get himself back in power. Meanwhile, Liz gets a visit from a caseworker from the adoption agency.
Liz sits next to Oprah on her flight from Chicago to New York, Tracy and Jenna conduct a "social experiment" to settle a dispute, and Kenneth is disillusioned when he learns that some Olympic events were actually staged.
Jack ignores Liz's warnings and hooks up with her psycho ex-roommate from Chicago. Meanwhile, Tracy reunites some of the cast of Night Court for Kenneth, who is down about the changes in the pages' uniforms.
After Don Geiss wakes from his coma and tells Jack that he plans to remain as CEO, a snow-in forces Jack to go with Liz to her high school reunion--where Liz learns, much to her surprise, that she was the class bully.
Jack accidentally hits his mother with his car and he is nursemaid as she recuperates. So he makes the staff put on a Christmas special. Liz's mom is not hosting a family Christmas so Liz buys toys as part of a 'Letters to Santa' program.