- Dean Lila Bolander, Dean of Admissions and Professor
- Dean Borak, Dean of Pennbrook
- Chancellor Murphy, Bridget Murphy's father
- George Feeny, Professor
- Writing Professor in How to Succeed in Business
- Physics Professor in Ain't College Great?
- Another Professor, cohort of the physics professor
- Guidance Counselor Myron
- Professor Cookmand, Drama Professor
- Stuart, Philosophy Professor (formerly)
- Their sports team was the Pennbrook Penguins.
- Lost 20 years running to their rival, an Amish school. In real life, the Amish for the most part only complete elementary education, believing vocational skills are sufficient for their society.
- Pennbrook Middle School is a real school in Pennsylvania.
- Jack, Rachel and Eric graduated from Pennbrook in 2000; however, it is hard to imagine Eric graduating a 4 year program in 3 years.