Discussion Questions For This Boy’s Life
1. Consider the book's epigraphs: "The first duty in life is to assume a pose. What the second is, no one has yet discovered."—Oscar Wilde. "He who fears corruption fears life."—Saul Alinsky. Why did the author choose these quotes? Do you think they fit the themes explored in This Boy's Life? Describe the primary pose assumed by each character. Is there tension between these poses and those of other "corrupt" ones that surface.
2. When applying to prep schools, Toby writes all of his own letters of recommendation and transcripts. He justifies this by suggesting that only he knows the truth about himself. Do you think this assertion applies to everyone? Who do you think is the true Toby? Why?
3. Alienation defines much of Toby's childhood, in part because of his fractured family. Once settled in Chinook, his mother, Rosemary, attempts to recreate a "real" family. Toby writes, "But our failure was ordained, because the real family we set out to imitate does not exist in nature" (112). Do you agree with this statement? Do you think the perfect family is a myth? What expectations does Toby have of his family?
4. After Toby moves to Chinook to “try things out,” Rosemary asks if Dwight and Toby are getting along, Toby lies: "I said we were. He was in the living room with me, painting some chairs, but I probably would have given the same answer if I'd been alone" (105). Why can't he tell his mother about Dwight? How does his lie relate to question #3?
5. The residual influence of fathers plays a prominent role in the story, hinging on brief glimpses of Rosemary's father, referred to as Daddy Roy (59-60), then Dwight as step-father, and the late emergence of Toby's biological father from back East. Compare the influence of these fathers on their children.
6. "But what I liked best about the Handbook was its voice, the bluff hail-fellow language by which it tried to make being a good boy seem adventurous, even romantic. The Scout spirit was traced to King Arthur's Round Table" (103). What does this passage reveal about the imaginative space in which Toby lives? How does it relate to his struggle with identity and community? How does this relate to the title? (Hint: It is Scout-related.)
7. Toby's botched attempt to run away to Alaska (160-68) may be one of the more heart-wrenching episodes in the narrative. Why does Toby disregard the urging of his friend Arthur at the Gathering of the Tribes? Why do you think Toby is unable to carry out his plan? Discuss the conflict between Toby's desire for freedom and his desire to belong. Compare this incident to when Toby nearly gets caught writing a bad check at the corner drugstore. How does Toby regain his composure (198)?
8. Who are Toby's friends and why does he choose them? Consider what they have in common and how they are different (e.g. Chuck vs. Arthur). Why does Toby treat Arthur so poorly at the carnival?
9. The memoir is set mostly in rural Washington, high in the forested mountains. The author uses the weather common to this area as a metaphor for Dwight's badgering: "I experienced it as more bad weather to get through, not biting, just close and dim and heavy" (100). How else does the stark Northwestern landscape enter and influence the narrative? Contrast the depiction of exterior spaces with that of the stark white interior one in which the family lives.
10. Consider the final segment of the book titled, "Amen." Why do you think Tobias Wolff chose to conclude the memoir this way?