Liz and Jenna's free-spirited friend Claire (Jennifer Aniston) visits New York and falls hard for Jack. Kenneth, distressed over the new page uniforms, turns to Tracy who cheers him up with a surprise involving the cast of Night Court.

Liz is opposed to going to her high school reunion, but Jack manages to convince her otherwise. Meanwhile, Don Geiss (Rip Torn) wake up from his coma only to shock Jack with his declaration of who will be GE's CEO.