A famous actor, Bobby Moore, once Nick's roommate, comes to Nick's class to research a movie role as a class clown. While Nick idolizes Bobby, he is also jealous of Bobby's success and insecure about his own decision not to pursue acting. At first, Bobby's antics are amusing, but he soon disrupts the class and shows disrespect for the literature that Nick teaches. Nick realizes that he is proud to be a teacher. Later, after Elana declines a date with Nick, he sees her at a restaurant with Bobby. Nick angrily confronts Bobby and tells Elana that he is attracted to her. Elana admits that she liked what Nick said. Meanwhile, when Davey has trouble learning material for a scholastic contest, Nick devises an innovative way to teach him.

Mezz wants to date Diane Fox, the school's sexy computer specialist whom he has known since they attended school together. Diane was never interested in Mezz because she is adventurous, so Nick vows to remove Mezz's inhibitions. Nick invites Mezz, Diane and Elana to dinner at a restaurant on top of a tall building. While the women are in the bathroom after dinner, Nick and Mezz climb out onto an overhanging gargoyle. Instead of being impressed, their dates have no idea where they went. Stranded, the guys must be rescued by a police helicopter. Meanwhile, when Fust rejects the students' ideas for the school newspaper, the kids revolt in pursuit of journalistic freedom.

When the school experiences a severe budget crisis, Emerson announces a carnival to earn revenue. While everyone is planning the event, Jordan begins arriving late to school and failing to do his homework. Nick meets with Jordan's parents and discovers that Jordan may be unhappy because they constantly bicker. Nick thinks he has helped Jordan's parents' relationship, but Jordan later blames Nick for their upcoming divorce. Even worse, Jordan ignores his friends and drinks alcohol during school. Meanwhile, the budget problems seem to have no effect on Mezz, who easily acquires all the supplies he requests from Emerson. But Mezz soon realizes that Emerson is overcompensating because he is black and she is afraid of treating him differently.

Sophia adores the baby of her friend Annie, until Sophia must baby-sit during a study session at Sophia's home. When Annie doesn't return until the next morning, Sophia confronts the reality of parental responsibility. Meanwhile, Mezz finds out that grouchy Yaroker has a weakness for cute babies. Nick's love life couldn't get worse when his first date with a woman is also his last with her. Emerson advises him, suggesting that Nick may be afraid of commitment.