Tobias Wolff, This Boy's Life, pp. 3-84
When we talk about the book in class, we'll be starting with the opening quotes from Oscar
Wilde and Saul Alinsky, so I'd like you to think about them--and to keep them in mind as you
read the novel.
Fortune
1. Look at the book's opening paragraphs, which establish our mental pictures of Toby and
his mother. What character traits do we see in each? What is distinctive about this
particular mother/son relationship?
2. The book opens very dramatically with the truck going over the cliff; how might this
event also have a symbolic component in the story Wolff is telling?
3. What do we know about Toby's parents' backgrounds? How do their life experiences
affect Toby's life?
4. As we meet him, Toby is in the process of changing his name to Jack; what
transformation does he hope this change will inaugurate? (On p. 8, he describes the first
of his intended transformations, a theme that will be echoed throughout his teen years as
the novel unfolds.)
5. Are such transformations really possible? If so, how do they actually occur? How would
you set about changing yourself if you wanted to do so? Have you ever done so?
6. Ben Franklin also believed in people's potential ability to recreate or transform
themselves into the persons they want to be. What does he have in common with
Toby/Jack? How are they different?
7. Why have Toby and his mother moved to Utah? What are they going to do when they get
there?
8. How do we discover that Toby really wants to be part of a "normal" family, that he
particularly misses having a father? What's peculiar about his family structure?
9. While in Utah, Toby takes catechism lessons and learns archery. How are these two
activities related? Which has the strongest impact on him? Why?
10. What kind of person is Roy? What qualities does he have that both attract and repel both
Toby and Rosemary? What kind of relationship does each have with him?
11. What's the significance of getting a gun for his birthday for Toby? Why doesn't his
mother want him to have one?
12. This section ends as the two flee on a Greyhound bus; how do they decide their
destination? How is this decision-making process typical?
Uncool
1. What are the common bonds between Terry Taylor, Terry Silver and Toby? How do the
Terrys differ? How are their families distinguished from each other?
2. How do the boys amuse themselves? Make a list of their activities and see what kind of
picture you get from it.
3. Why might you be particularly shocked that Terry Silver is anti-Semitic? What does that
fact tell you about him?
4. What happens when Toby and Rosemary go to the mock naval battle and meet Judd and
Gil? We hear about it from the point of view of an eleven-year-old boy; what can we
deduce from what he doesn't say?
5. How does the flashback to Rosemary's childhood illuminate the Judd and Gil episode?
How does it help explain her relationship with Roy? (You might note also that it
foreshadows the relationship she's about to start with Dwight.)
6. The adventures with the two Terrys escalate in violence and damage. What impact does
this have on Toby's mother? What do her two housemates contribute to the situation?
7. On pp. 63-64, we find the first description of Dwight; what do he and Toby have in
common?
8. What makes Thanksgiving such an appropriate setting for the first visit to Dwight in
Chinook? How do the events at the Turkey shoot suggest new insights into Dwight's
character?
9. The visit's closing image (p. 75), of the salmon rotting in fresh water, seems to echo the
book's opening, in which the truck loses its brakes, crashing and burning. As you
continue to read, note where we find recurring images of losing control, of crashing or
falling apart.
10. Why does Rosemary decide to send Toby to live with Dwight? What does she believe he
needs? Do you agree?
Tobias Wolff, This Boy's Life, pp. 87-178
Before starting on the reading questions, I'd like you to think recall some of the central issues
from the earlier section, so they'll be with you as you think about the middle sections of the
book. Some things to think about are:
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Toby's relationship with his parents and the role of families in their children's lives
Images of crashing, falling or falling apart
The possibility of taking on roles, of transforming yourself into another person, of
changing your life
The idea that you are potentially someone else, someone quite different from the one
other people perceive
A Whole New Deal
1. In this section, Dwight becomes the major force in Toby's/Jack's life. How does the
opening incident with the beaver signal the nature of this force? As you read the next
section, you should note what finally becomes of the beaver. How is it finally
transformed into something else?
2. Why does Toby agree to go to Chinook? Why do you think he doesn't tell his mother
what his life with Dwight is really like?
Citizenship in the Home
1. This section and the next have parallel titles, both centering on citizenship, another
reminder of Ben Franklin's Autobiography. What directly influences the theme of
citizenship? What does "citizenship in the home" mean to Wolff?
2. As you read the first pages of this section, think about Dwight's attitude toward Toby.
Why does he seem so hostile to him? Dwight is a very complicated character, made more
so since we see him only through Toby's eyes; be ready to talk about Dwight and his
motivations in our discussion.
3. What is it that Toby particularly misses about his mother?
4. What do the Boy Scouts come to mean to Toby? One thing he particularly likes about the
Scout Handbook is its use of "numbers and lists" (p. 103). Why do these things appeal to
him so strongly?
5. Boy's Life, the scout magazine, gives the novel its title. How is This Boy's Life different
from Boy's Life? Where do you see them intersecting?
6. Why do you think Toby feels compelled to "take as my father a man who was offended
by my existence and would never stop questioning my right to it" (p. 105)? How accurate
do you find his assessment of Dwight to be?
7. What do Dwight and Toby do to prepare for Rosemary's arrival? Is this activity
significant in any way? What happens to her after she marries Dwight? How does she
help herself recover?
8. What does Toby learn from his fight with Arthur? What does it reinforce in his
relationship with Dwight? Why do Toby and Arthur become friends?
9. What was your first clue that Toby (and Tobias Wolff) finds cars fascinating? What, if
any, is the moral of the story of Skipper's candy-red Ford?
10. What does Toby think about his father, whom he hasn't seen or heard from in years?
What causes the adult Tobias Wolff to reassess his father's treatment of him?
11. How does Toby turn even an embarrassing evening playing basketball in street shoes into
an occasion for heroic fantasy? What does this signal about his connection to the world
around him? What accounts for his increasing difficulty seeing events in anything other
than his own perspective?
12. Why does Toby continue to steal from his paper route customers? What accounts for his
growing conviction that you can literally get away with murder if you "appear in the right
role, like Cheryl Crane when she stabbed Johnny Stampanato to death for threatening
Lana Turner" (p. 133)? Do you agree with this conviction?
13. What causes Toby to lose the ability to feel guilty about any of the things he's doing?
14. The trips home from the tavern are a recurring motif in this section of the book, always
taking the same basic form. Why are they such an important part of This Boy's Life?
15. Why does Wolff tell the story of his proposed move to his uncle's house in Paris? What
realization finally leads him to refuse to go?
16. The story of Norma's fiancé gives Wolff another chance to describe a holiday in this
dysfunctional household. What's Christmas like at Dwight's house in Chinook? What
does Kenneth add to the mix?
17. On Christmas Eve, the family watches Dwight's favorite TV program, The Lawrence
Welk Show. It's described in detail in a very funny couple of pages, in which the program
reminds Dwight of the horse chestnuts in the attic. What's the sequel to that story? (Are
horse chestnuts actually edible, by the way?)
18. What holds Arthur and Toby together as friends? What starts to drive them apart? How
does the Scout Gathering bring several plot strands together? How are they resolved? Do
you see any echo of the story of Skipper's car in this section?
19. When, in later years, Rosemary asks Toby, "Why don't you take a little ride with
Dwight?" what does she mean? How does the story of Champ the dog bridge the gap
between stories of home and stories of school?
Tobias Wolff, This Boy's Life, pp. 181-280
Citizenship in the School
1. Having mastered "citizenship in the home," Toby now moves on to "citizenship in the
school." What does Wolff mean by "citizenship" anyway?
2. In what sense can we see Toby as self serving and/or manipulative in this section? What
reasons can you suggest for his behavior?
3. As Toby moves away from life at his house in Chinook, one theme that was subtly
introduced in the last section becomes a dominant chord here: the class differences within
this community and how they translate into the adult life the various teenagers can
expect. What do Bobby Crow, Chuck Bolger, Huff, Psycho, Arch, Veronica and Tina
Flood all have in common? How is this connection reinforced by the rural community in
which they live?
4. Do you think class and environment still operate in the same way today? Why or why
not?
5. When Toby starts high school in Concrete, he describes the physical situation of the
school. How does this description connect to the images that opened or closed earlier
sections of the book?
6. How would you describe the intellectual atmosphere at Concrete High? Do you think
Wolff is giving us an accurate picture? Explain.
7. Why does Toby lose touch with Arthur as they start high school? Why do you think he
chooses the friends he does?
8. What makes Chuck so self-destructive? Why does Toby like him so much? What finally
causes the two of them to drift apart?
9. Toby wants to be promoted to Eagle Scout, but Dwight won't send in the papers. Do you
think he deserves to be an Eagle Scout? Should he really get the badge "Citizenship in the
Nation"? What symbolic meaning has scouting taken on in this novel?
10. What does the incident with the mustard bottle tell us about Dwight, Pearl and Toby?
How does this incident trigger a major change in Toby's life?
11. Why does Toby want to go to prep school? What does he value about a prep school
education? What is he prepared to do to get there? What is he not prepared to do?
12. When Toby got hold of Vance Packard's The Status Seekers, he suddenly develops a love
for reading as intense as Franklin's. What's the difference between their respective
reading choices? What does each hope to gain from his reading?
13. What does Toby like about the Lakeside school in Seattle? How does it differ from
Concrete High? What makes it possible for him to even contemplate the possibility that
he could move out of Concrete and into such a setting?
14. "[In] the splendid phantom who carried all my hopes, it seemed to me I saw, at last, my
own face," Toby concludes his description of his transformation into a prep school boy.
What's chilling about those words?
15. The story of the fight with Arthur sheds further light (if we needed it) on the problems
inherent in going to school in Concrete in the fifties--but it also gives Wolff a chance to
reflect on what it was he really learned from Dwight. On p. 221, and again on p. 232, he
tells us quite clearly what he sees as the nature of Dwight's continuing influence on him.
What does he describe?
16. What finally brings the marriage between Toby's mother and Dwight to an end?
The Amen Corner
1. Toby and Chuck each respond differently to the Welch family. Why? How is this related
to their respective backgrounds and future plans?
2. Why do you think Toby has become unable to communicate with anyone by the time he's
finishing his second year at Concrete High? How is his conversation with Father Karl
emblematic of this difficulty? What does he most want in the world? What's he willing to
do to get it? What is he not willing to do?
3. Why does Chuck refuse to marry Tina Flood? How is his refusal related to his own plans
for the future? Do you think he'll get what he hopes for? Why or why not?
4. When Toby gets his scholarship to Hill, he changes his name yet again. What is it going
to be this time, and what's the significance of the name he chooses?
5. How does Toby pay Dwight back for stealing his money and his gun and for all the years
of abuse? Why can't Chuck understand Toby's need to do this?
6. Mr. and Mrs. Howard take Toby out to buy the clothes that will complete his
transformation into the fictional von Ansell-Wolff. When Toby finally looks at himself in
the mirror, what does he see? What does the older Tobias Wolff, looking back in
memory, see? Why are their perceptions so different?
7. As this section closes, we have the Toby known to the Howards contrasted with the Toby
known to Chuck. How far apart are the two? What do you see as the difficulties in getting
these two roles in sync? Can it be done, in your opinion?
Tobias Wolff, This Boy's Life, pp. 283-288
Amen
1. Here we're wrapping up the loose ends for those of us who want to know 'what happened
next.' How does the summer in California go?
2. What finally became of Dwight? What does Rosemary's behavior in that section tell us
about ways in which she might have changed since the time in Chinook?
3. "When we are green, still half created, we believe that our dreams are rights, that the
world is disposed to act in our best interests, and that falling and dying are for quitters.
We live on the innocent and monstrous assurance that we, alone, of all the people ever
born, have a special arrangement whereby we will be allowed to stay green forever." (p.
286) Explain.
4. Why does this comment for the older Tobias narrator introduce the final scene of the
novel? Why, after telling us what happened to virtually all the characters in the next few
years, does Wolff return to the day Chuck drove Toby to Seattle?
5. What role do cars play in Toby's life?
6. The book begins and ends with Toby in a car singing with the driver; is there any
significance to this?