Chapters 1-7   |   Chapters 8-13   |   Chapters 14-20   |   Chapters 21-26

Chapter One (1-6)

1. Where is the narrator (Holden Caulfield) when he writes his story about the "madman" time he had around last Christmas?

2. Why is he dissatisfied with his brother's success in Hollywood? Why  does he say his brother is a prostitute?

3. Identify some  things Holden doesn't like about Pencey Prep.  (A prep-school or preparatory-school, is an expensive private high school where parents pay tuition.)  Do his claims seem exaggerated?

4. What kind of memory was Holden trying to remember about Pencey so he could say "good-bye" to the place?  Compare the memory he retrieves with his recent mistake with the fencing equipment.  What kind of "good-bye" is he trying to achieve.

5. Based on your reading of the first chapter, predict which feelings and ideas will be important in this novel?

Chapter Two (6-16)

1. When Holden visits Mr. Spencer, his teacher tells him that life is a game, a game with rules, and Holden agrees. What does Holden really think?  What is your response to his duplicity?

2. If you are keeping a character list, put Spencer on it  and describe him.

3. When will Holden's  parents learn that he has been kicked out of school? When will he see them?

4. What does Spencer do that Holden calls a "dirty trick"? Why does Holden think it is unfair?  Include details in your answer. 

5. Spencer asks Holden about the other schools he's been kicked out of—the Whooton school and Elkton Hills. Why did Holden quit working at Elkton Hills?

Chapter Three (16-26)

1. Holden's dormitory is named after a man called Ossenberger because he donated a lot of money to Pencey Prep.  What did this man do for a living? Why does Holden think Ossenberger is a phony?

2. What did Holden purchase in New York  when they exited  the subway and discovered the foils were lost?

3. Put Ackley and Stradlater on your character list and describe their distinguishing traits.

Chapter Four (26-35)

1. Ironically, what does Stradlater ask Holden to do?

2. How does Holden react when Stradlater mention his date?  Why do you think he reacts this way?

3. Put Jane Gallagher on your character list and describe her.

4. Why does he admire the fact that she keeps her kings in the back row?

5. Why doesn't he go down to see her while she waits for Stradlater?

Chapter Five (35-39)

1. According to Holden, why does Pencey Prep serve steak every Saturday night?

2. Holden invites Ackley to the movies. What does this say about Holden's personality or his mood?

3. What is the composition about? Was this a good subject? Why or why not?

4. Put Allie Caulfield on your character list and describe him.

5. What did Allie die of, and how old was he when he died?

6. What year is the book set in?

7. What did Holden do the night Allie died? What was he feeling?

Chapter Six (40-46)

1. Holden begins the chapter saying "some things are hard to remember," and then he explains that he can't remember clearly because he was so worried at the time. What was he worried about?

2. What does Stradlater think about the composition? What is Holden's reaction?

3. Why does Holden smoke in the dorm room?

4. When Holden asks Stradlater if Jane she still keeps her kings in the back row, Stradlater says, "What the hell you think we did all night--play checkers, for Chrissake?" Give two reasons why this is mean.

5. What does Holden call Stradlater that finally convinces him to punch him?

6. Do you think Stradlater understands why Holden is so upset?

7. Is Holden heroic?  Why or why not?

Chapter Seven (46-52)

1. With his nose bleeding, Holden steps into Ackley's room. Ackley wants to know what caused the fight. Does Ackley care that Holden is hurt? Why or why not?

2. What does Holden think of when he looks out Ackley's window?

3. After leaving Ackley's room, Holden makes an important decision. What is it and what is his plan?

4. At the end of the chapter Holden is crying. He says he doesn't know why? Do you?

5. Why does he almost break his neck on the stairs?

Chapter Eight (53-58)

1. On the train to New York a woman sits next to Holden. It turns out her son, Ernest Morrow, is a student at Pencey. What kind of person is he? Put him on your character list.

2. Why does Holden lie to her about her son?  Why does he lie when she asks him why he's going home?

3. What lie does he tell about himself?  What is the appeal of such a lie?

Chapter Nine (59-66)

1. What does Holden want to do when he gets to Penn Station in New York? Does he do it?

2. What does Holden ask the cab-driver? When was the last time he wondered this?

3. Describe the people on the other side of the hotel.  Can you relate to Holden's ambiguous feelings—are things sometimes both attractive and repulsive?

4. What was the sex rule Holden made and then broke the day he made it? Was his rule a good idea or not?

5. Holden calls Faith Cavendish. Why? Why is he mad at himself at the end of the chapter?

Chapter Ten (66-76)

1. Put Phoebe on your character list and describe her.

2. Whom does Holden meet in the lavender room? How old are they?

3. What does he admire about the blonde? What is she interested in?

4. Holden thinks the girls are stupid because they don't take him seriously and don't keep up their part of the conversation. Do you think they're stupid? Why or why not?

5. What is Holden's emotional state at the end of the chapter?

Chapter Eleven (76-80)

1. Why do you think Jane doesn't answer her step-father?

2. What does Holden ask her about her step-father?

3. Does this chapter give you any insight into Holden's feelings for Jane? Does it explain why he was so worried about her date with Stradlater?

4. Where does Holden decide to go next?

Chapter Twelve (81-87)

1. What kind of guy is Horowitz? Put him on your character list.

2. How does Horowitz explain how the fish survive in the ice? What is the question he asks Holden before he drives off?

3. Why does Holden think Ernie is a phony?

4. Why does Holden hate the "Joe-Yale looking guy"?

5. Why does Holden have to leave?

Chapter Thirteen (88--98)

1. Holden decides to walk the forty-one blocks back to his hotel. What is the weather like?

2. Along the way Holden thinks about how his _______ were stolen and how he would be too _______________ to punch the guy you took them even if he caught them red-handed.

3. Once back at the hotel, what does Holden agree to despite the fact that it was "against my principles"?  Why does he say he agreed?  Why do you feel he agreed?

4. Holden regrets that he stops when girls tell him to stop. Should he?  

5. Put Sunny on your character list. What's ironic about her name?

6. What happens between Sunny and Holden? What do they disagree about?

7. Why is Sunny "spooky"?

Chapter Fourteen (98--104)

1. After Sunny leaves whom does Holden talk to? What is he remembering?

2. Once in bed Holden feels like praying, but he can't. Why?

3. Do you think Jesus would have sent Judas to hell? Why or why not?

4. Who knocks on the door and why? What happens?

5. Why doesn't Holden jump out the window?

 Chapter Fifteen (105--113)

1. Who doesn't Holden telephone? Who does he call instead?

2. Is Holden a snob because of his opinions about suitcases?

3. Who sits next to Holden at breakfast?

4. What does he wonder about the English teacher?

Chapter Sixteen (113--122)

1. When Holden compares the nuns to other women, how does he feel about them?

2. What does Holden buy for Phoebe?

3. What is the little boy doing as he sings? What does he sing?

4. Looking for Phoebe, Holden helps a kid in the park. How does he help her? What is it about kids that Holden likes?

5. What is the "best thing" about the Natural History Museum?

6. Holden thinks the museum is great, but he doesn't go in. Why?

Chapter Seventeen (123--134)

1. What is depressing about watching the girls?

2. How does Holden really feel about Sally? What does he want to do as soon as he sees her?

3. What word does the Andover boy use that Holden despises?

4. Why does Sally want to go ice skating?

5. Was Holden shouting when he was talking to Sally in the bar?

6. What fantastic idea does Holden suggest to Sally?

7. What does Holden regret saying?

Chapter Eighteen (135--141)

1. Is the Christmas show at Radio City religious? Would Jesus like it?

2. Why isn't the woman at the movies kind-hearted?

3. Why was D.B. glad he didn't have to shoot anyone in W.W.II?

4. What war duty does Holden want to volunteer for?

Chapter Nineteen (141--149)

1. What kind of talks did Carl Luce give at the Whooton School?

2. What does Holden wonder about Luce?

3. Holden tells Luce that something screws up his sex life. What is it?

4. What does Luce recommend to Holden?

Chapter Twenty (149--157)

1. What does Holden do after Luce leaves?

2. What fantasy does he play out (for the second time)?

3. Holden doesn't telephone __________ because he isn't in the _________.  Instead he calls _______________.

4. What does he want to tell her?

5. Is she a good sport about it?

6. What does Holden put his head into and why? Was this a good idea?

7. On his way to see the ducks, something "terrible" happens.  What is it?

8. Holden decides he'll probably get pneumonia and die. What does that make him think about?

9. Where does he decide to go and why?

Chapter Twenty-one (157--166)

1. Why isn't Phoebe in her room?

2. What does Holden think about sleeping kids? Why does he think that?

3. What was Phoebe's letter about?

4. What is Phoebe's reaction to the broken record? What does this say about her? Add to your character list.

5. What does she figure out?

Chapter Twenty-two (166--174)

1. What example does Holden give to explain how mean the guys were at Pencey.

2. When challenged by Phoebe to say what he likes, what three things does Holden think of?

3. What happened to James Castle at Elkton Hills?

4. What does Holden want to be?

5. Who does Holden call?

6. What kind of lessons is Phoebe taking? What does this show about her?

 Chapter Twenty-three (174--180)

1. What did Antolini do that Holden hasn't forgotten?

2. What does Holden borrow from Phoebe?

3. What does he promise her he won't miss? When will it be?

4. Why does he cry?

5. Why was it easier getting out of the house than it was getting in?

Chapter Twenty-four (180--193)

1. How does Holden describe Mrs. Antolini?

2. What does digression mean?

3. What did Holden hate about his speech class?

4. What is especially "horrible" about the "fall" Antonlini thinks Holden is "riding for"?

5. Write down the quote that Antolini gives Holden.

6. What happens at the end that makes Holden leave?

Chapter Twenty-five (194--213)

1. Holden spends the night at Grand Central Station. How does he sleep?

2. What doubts does he have?

3. What does the magazine article convince him of?

4. Why does Holden almost vomit?

5. What "spooky" thing begins to happen to Holden as he crosses streets? How does he deal with it?

6. What new plan did Holden come up with?

7. Why is Holden upset when he sees the words "fuck you" written on the wall?

8. What does Phoebe bring with her and why?

9. What does Holden say to her? Why does he hate her and want her to cry?

10. Where do they go and how does Holden feel at the end of the chapter?

Chapter Twenty-six (213--214)

1. What is the "stupid question"?

2. Who does Holden miss at the end? What suggestion does he make to the reader?

3. Write an evaluation of the book. Would you recommend it? Did you like it? Why or why not?

Chapters 1-7   |   Chapters 8-13   |   Chapters 14-20   |   Chapters 21-26