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.
Liz tries to make a stand and refuses to take a flu shot in a show of solidarity with her coworkers--until she discovers that her island vacation is not canceled. Meanwhile, Jack and Elisa break some rules to begin dating.
After an Asian economic meltdown, Tracy gives some irresponsible advice on "Larry King Live," and Jack and Elisa's relationship could be in jeopardy. Meanwhile, Liz tries to get her cell phone back from a cabbie who's blackmailing her.
Jack gets the writers to come up with a name for GE's new pocket microwave, Liz unsuccessfully tries to get out of jury duty, Dr. Spaceman gives Jenna pills to help her stay awake, and Tracy deliberately tries to get fined by the FCC.
Liz feels uncomfortable when she joins his unusually handsome boyfriend in "the bubble," Tracy decides to quit the show rather than negotiate a new contract, and Jenna tries to cut her hair for publicity and attention.
Jack tries to turn an accidental obituary for Jenna into a marketing opportunity for her Janis Joplin-based biopic. Meanwhile Liz makes friends with a group of single women while away from work for sexual harassment.
Jack has second thoughts about marrying Elisa when he finds out she killed her first husband for cheating. Meanwhile, Jenna tries to hook up with a sexy paramedic, and Tracy's wife asks him to get a tattoo of her.
Jack brings in several famous musical artists to perform a benefit song so his biological father can get a kidney, Tracy is afraid to speak at his high school's graduation, and Liz finds a talent in giving irresponsible relationship advice.