The dedication of Old School reveals something of how Wolff might feel about his own education. If you wrote a book, would you dedicate it the same way?
What does the epigraph of Old School, a passage from a Mark Strand poem, mean? How does it relate to the novel's thematic concerns?
Why do you think Wolff left the narrator and even the school unnamed?
In Chapter One, the narrator maintains that his school disregarded issues of wealth and social background and judged its students entirely by their actions. Does this turn out to be true? How does his school compare to your own?
Early in the novel, the narrator says that his aspirations as a writer "were mystical. I wanted to receive the laying on of hands that had written living stories and poems, hands that had touched the hands of other writers. I wanted to be anointed." What does he mean by this?
Which of his classmates does the narrator feel closest to, and why?
How do the narrator's changing attitudes toward his grandfather demonstrate his process of maturing?
Discuss the portrayals of Robert Frost, Ayn Rand, and Ernest Hemingway. How does each influence the narrator?
Why might Chapter Six be titled "The Forked Tongue"? What are the larger implications of its very last sentence?
Why does Mr. Ramsey show such disdain for the use of the word "honor"? Do you agree with his attitude?
Over the course of the novel, the narrator writes two letters to girls. The circumstances differ, but he has the same reaction after sending each letter. What does this pattern of behavior reveal about his personality?
Why is the narrator shocked by Susan Friedman's attitude toward her own story, and toward writing in general? How valid is his unspoken response to her comments?
Why does the narrator feel such love and loyalty for his school, despite his final punishment?
The last sentence of the book is from the New Testament parable of the prodigal son (Luke 15:11-32). How might these be "surely the most beautiful words ever written or said"?