Greg breaks his cardinal rule and spends time with Rachel at school – in front of people. While hanging around Rachel, Greg gets to know the “Upper-Middle-Class Senior Jewish Girl Sub-Clique 2a” (114), which includes Naomi Shapiro and Anna Tuchman, neither of whom Greg particularly cares for but tolerates because they are Rachel’s friends.

Against his better judgment, Greg agrees to have lunch with them in the cafeteria one afternoon, a repulsive condiment-throwing, cheese-slicked room he’s not “set foot in for years” (116), when Madison Hartner joins them at their table. Madison is the “insanely hot girl” whom Greg made cry in the fifth grade with his incessant insults, and his crush on her endures to this day (118). According to Greg, Madison falls into one of two categories of hot girls: she’s not an “Evil Hot Girl,” so she’s a member of the “Hot Girls Who Are Also Sympathetic Good-Hearted People and Will Not Intentionally Destroy Your Life” (119). Greg warns that even though the latter category of girls does not intend to harm you doesn’t mean they won’t. Unsure when, if ever, this opportunity will present itself again, Greg finds a way to make Madison laugh by poking fun at his lunch.