Liz and Jenna are expecting a visit from their old Chicago roommate, Claire. Liz says that Claire is exhausting and she doesn't know if she can keep up with her. A few minutes after Clair gets there, she invites them to an underground party.
Jack is attracted to Claire, and Liz warns him that she is crazy and not one to get involved with. Jack breaks the news that it's too late because he already slept with in the elevator, a few minutes after their initial meeting. Jack tells Liz that she is just jealous of Claire because she took away Liz's boyfriend many years ago.
Kenneth is sad due to the new page uniforms. Tracy wants to see Kenneth smile again so he gets Harry Anderson, Markie Post, and Charlie Robinson from Kenneth's favorite show, "Night Court" to meet with him. Kenneth tells them that this is the "greatest day of his life."
At a formal function, Claire serenades Jack by singing "Happy Birthday" in front of all of his GE colleagues. He takes her to the side and assures her that it is not his birthday and tells her that she needs to leave. Claire goes crazy and loudly threatens to commit suicide. Jack sees that Claire truly is not right in the head.
Kenneth is excited when he finds out that he can watch the "Night Court" wedding between Harry and Christine, the way it was promised to him by NBC years before. His dream is taken away when Markie Post and Harry Anderson fight and Markie walks off the set. Tracy does his best to convince Markie and Harry to make up and rehearse.
To help Jack, Liz gets Claire to get rid of her plans with him and go clubbing instead. Liz and Jenna wait at the club and realize that Claire is not going to show. They call Jack and warn him about potential danger. He finds Claire inside of his house and ends up sleeping with her again.
Liz sees Kenneth and Tracy shooting their "Night Court" reunion on the set and she tells him they have to shut it down. Kenneth pleads to continue the Harry and Christine wedding skit and they all gather for a big group hug.
Jack and Claire are waiting in line for a club. Claire realizes that now that she is with Jack, Liz isn't trying to impede in their relationship anymore. Because of this, she feels the relationship is getting boring. To prove that they are not boring, she plants a gun on Jack and tells the cops to chase him. Jack finally realizes that she really, truly is psycho.
As Tracy and Kenneth finish taping the final scenes of Christine and Harry's wedding, Harry declares it illegal to wear the new page uniforms. He demands the old ones should be brought back. Tracy tells Kenneth that he added that part in the scene especially for him, and Kenneth is delighted.