1. HOW I PAID FOR COLLEGE has been described as "if David Sedaris had re-imagined THE CATCHER IN THE RYE." Do you think the analogy to THE CATCHER IN THE RYE is appropriate and, if so, how?
2. The book is set in the fictional bedroom community of Wallingford, NJ. Could it have been set in another part of the country and, if so, where and why?
3. The story takes place in 1983-84, Ronald Reagan's "Morning in America." How do you think the Reaganite atmosphere affects the behavior of the characters? How are today's teenagers different from those in the 1980s and how do you think they would act in similar circumstances?
4. During the book, Edward is confused about his sexuality. What do you think of this confusion? Is he straight, gay or bisexual? How does his sexuality impact his plans and schemes?
5. In most classic coming of age stories, the parents are either absent, unavailable or dispensed with quickly. (Think of Holden Caulfield, Huck Finn and Harry Potter.) What is the point of having the parents absent and what do you think would have happened if Edward's parents had been around?
6. What role do the supportive adults (Aunt Glo, Mr. Lucas and Kathleen) play in Edward's life?
7. HOW I PAID FOR COLLEGE is in development at Columbia Pictures to become a major motion picture. Who do you see playing the characters?
8. Edward and his friends are obsessed with musical theater. What do the musicals discussed (GREASE/A CHORUS LINE, PIPPIN/YENTL) illustrate about the characters?
9. When Edward visits Mr. Lucas' apartment, Mr. Lucas talks about how books gave him a reason to live after his accident ("I kept reading, just to stay alive. In fact, I'd read two or three books at the same time, just so I wouldn't finish one without being in the middle of another--anything to stop me from falling into the big, gaping void"). What do books and reading mean to you?
10. Throughout the book, other works of literature are referenced (OEDIPUS REX, ANTIGONE, HAMLET, GREAT EXPECTATIONS, DAVID COPPERFIELD, PORTRAIT OF THE ARTIST AS A YOUNG MAN and GO TELL IT ON THE MOUNTAIN) How do these works relate to the themes in HOW I PAID FOR COLLEGE?
11. Throughout the book, various religious elements are present (a Buddha, a New Age mom, nuns and priests; Edward even plays Jesus in GODSPELL). Discuss the relevance of the religious imagery and its significance.
12. Along the same lines, discuss the relevance of Frank Sinatra.
13. In Greek drama, a deus ex machina refers to the entrance of a god (on a piece of stage machinery) who uses his divine powers to solve all the mortals' problems. HOW I PAID FOR COLLEGE contains a very intentional deus ex machina. How does it relate to the themes of the book?
14. The complicated plot is set in motion by Edward's overwhelming desire to be an actor. But, after reading the book, do you think Edward would be successful as an actor?
15. Is there a moral to HOW I PAID FOR COLLEGE?
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