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.
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.
Liz has to spend Christmas without her family for the first time in her life. As compensation she participates in a 'Letters to Santa' charity program and buys presents for poor children. Jack accidentally hits his mother with his car just before leaving to Rio. Now stuck with her in New York, he decides to force the cast of TGS into putting on a live Christmas Eve special so at least he won't have to go home.