The Great Gatsby, Ch.

1
1. What was the advice given to Nick by his father? How, do dinner? What does this book’s content show us about Tom?
you suppose, this makes him a good person to tell this story?
9. What is the reader left to think about Daisy’s emotional
2. What is Nick’s social class/background? How state and her
did his family make its money? relationship with
Tom?
3. When Nick returns from the war, why does he
decide to go East? 10. Who is Jordan
Baker, and what has
4. How is West Egg different from East Egg? Nick heard about
her?
5. Before meeting him, what does Nick tell us about
Tom Buchanan? 11. At the end of
this chapter, Nick
6. If you were going to pick one color to connect sees Gatsby on the
with Daisy Buchanan, what color would it be? lawn and is about
Explain your reasoning. to call to him and
introduce himself, but he does not. What stops Nick? What
7. We find out that Tom has “some woman in New York.” does Gatsby’s “trembling” suggest?
What unflattering feature of Jordan Baker’s personality is
revealed in this scene? 12. The green light that Gatsby is staring at will become an
important symbol in the book. What symbolic associations do
8. What’s the name of the book that Tom wants to discuss at you connect to the color green?

The Great Gatsby, Ch. 1

1. What was the advice given to Nick by his father? How, do dinner? What does this book’s content show us about Tom?
you suppose, this makes him a good person to tell this story?
9. What is the reader left to think about Daisy’s emotional
2. What is Nick’s social class/background? How state and her
did his family make its money? relationship with
Tom?
3. When Nick returns from the war, why does he
decide to go East? 10. Who is Jordan
Baker, and what has
4. How is West Egg different from East Egg? Nick heard about
her?
5. Before meeting him, what does Nick tell us about
Tom Buchanan? 11. At the end of
this chapter, Nick
6. If you were going to pick one color to connect sees Gatsby on the
with Daisy Buchanan, what color would it be? lawn and is about
Explain your reasoning. to call to him and
introduce himself, but he does not. What stops Nick? What
7. We find out that Tom has “some woman in New York.” does Gatsby’s “trembling” suggest?
What unflattering feature of Jordan Baker’s personality is
revealed in this scene? 12. The green light that Gatsby is staring at will become an
important symbol in the book. What symbolic associations do
8. What’s the name of the book that Tom wants to discuss at you connect to the color green?
The Great Gatsby, Ch. 2
1. The description of the “valley of ashes” opens this chapter. Literally, what is the valley of ashes? What might it
represent on a symbolic level?

2. Compare and contrast George Wilson and Tom Buchanan. Then, compare and contrast Myrtle Wilson and Daisy
Buchanan.

3. How do we know that Myrtle Wilson is not an

intellectual?

4. Notice how often and in what context Doctor

Eckleburg’s eyes are mentioned. Symbolically,
what might those eyes on that billboard represent?

5. What’s up with the puppy? Why do you

suppose Fitzgerald included it as an element in this
chapter?

6. Do you think Tom will leave Daisy for Myrtle?

Support your answer.

The Great Gatsby, Ch. 2

1. The description of the “valley of ashes” opens this chapter. Literally, what is the valley of ashes? What might it
represent on a symbolic level?

2. Compare and contrast George Wilson and Tom Buchanan. Then, compare and contrast Myrtle Wilson and Daisy
Buchanan.

3. How do we know that Myrtle Wilson is not an

intellectual?

4. Notice how often and in what context Doctor

Eckleburg’s eyes are mentioned. Symbolically,
what might those eyes on that billboard represent?

5. What’s up with the puppy? Why do you

suppose Fitzgerald included it as an element in this
chapter?

6. Do you think Tom will leave Daisy for Myrtle?

Support your answer.
The Great Gatsby, Ch. 3

1. Nick describes the people who attend Gatsby’s parties

and says “that once there, the guests conducted themselves
according to the rules of behavior associated with amusement
parks.” Given this, what can you conclude is Nick’s opinion of
Gatsby’s party guests?

2. Why does Jordan want to leave the group from East Egg?
Why does Nick want to leave the group?

3. Who is Owl-Eyes? What surprises him about Gatsby’s library?

Why would this impress him?

4. What unexpected common bond do Gatsby and Nick share?

5. Nick says, “I was looking at an elegant young roughneck...whose

elaborate formality of speech just missed being absurd. Some time
before he introduced himself I’d got a strong impression that he was
picking his words with care.” What is Fitzgerald trying to convey here
about Gatsby? How should we feel about Gatsby here?

6. Why do you suppose that Jordan does not believe Gatsby when he
says that he had attended Oxford College in England?

7. In what ways is Gatsby’s behavior at his party quite unlike the behavior
of most of his guests?

8. Toward the end of the party, we have the unflattering description of

husbands and wives and also the drunk who has crashed his car. What is
Fitzgerald’s deeper message to us here?

9. Jordan declares to Nick that she “hates careless people.” Explain the
irony here.
The Great Gatsby, Ch. 4
1. Looking through the list of party-goers, find and paraphrase at least three pieces of evidence that the old money is in East Egg and the
new money in West Egg?

2. What is weird about Nick’s drive into New York with Gatsby? List at least three things about Gatsby in this scene that strike you as odd.

3. What two things does Nick see on/near the Queensboro Bridge that make him think that
Gatsby is, perhaps, telling the truth?

4. Who is Meyer Wolfsheim, and what do we know about him?

5. Gatsby disappears when which other character unexpectedly arrives at lunch? Take a guess as
to why Gatsby doesn’t want to see this character.

6. Jordan recalls the time in 1917 when she saw Gatsby and Daisy together. From Jordan’s
description, do you think Daisy was genuinely interested in Gatsby?

7. How does Daisy behave the night before her wedding? Why?

8. Who, do you suppose, sent the letter that caused Daisy to become so upset? What do you think the letter may have said?

9. Nick says, “Then it had not been merely the stars to which he had aspired on that June night” when Nick first spotted Gatsby reaching
out across the bay. What does Nick now realize about that night and about Gatsby’s real estate purchase?

10. What’s happening between Nick and Jordan?

The Great Gatsby, Ch. 4

1. Looking through the list of party-goers, find and paraphrase at least three pieces of evidence that the old money is in East Egg and the
new money in West Egg?

2. What is weird about Nick’s drive into New York with Gatsby? List at least three things about Gatsby in this scene that strike you as odd.

3. What two things does Nick see on/near the Queensboro Bridge that make him think that
Gatsby is, perhaps, telling the truth?

4. Who is Meyer Wolfsheim, and what do we know about him?

5. Gatsby disappears when which other character unexpectedly arrives at lunch? Take a guess as
to why Gatsby doesn’t want to see this character.

6. Jordan recalls the time in 1917 when she saw Gatsby and Daisy together. From Jordan’s
description, do you think Daisy was genuinely interested in Gatsby?

7. How does Daisy behave the night before her wedding? Why?

8. Who, do you suppose, sent the letter that caused Daisy to become so upset? What do you think the letter may have said?

9. Nick says, “Then it had not been merely the stars to which he had aspired on that June night” when Nick first spotted Gatsby reaching
out across the bay. What does Nick now realize about that night and about Gatsby’s real estate purchase?

10. What’s happening between Nick and Jordan?

The Great Gatsby, Ch. 5
1. What steps has Gatsby taken to ensure this reunion day is perfect?

2. What’s the weather like at the beginning of the chapter? Symbolically analyze this element of the scene.

3. Why does Gatsby take Nick and Daisy the long away around his house to the front door instead of just cutting through the
back lawn?

4. When Nick asks Gatsby what business he is in, Gatsby responds, “That’s my affair,” before he realizes that this is not an
appropriate reply. Why does Gatsby give that answer, and why is not it an appropriate reply?

5. Okay, let’s talk about that scene with the shirts. Obviously, Daisy’s not crying because of the
actual shirts. Analyze the passage and explain what, exactly, has caused Daisy to become so
emotional as she wraps herself in all those shirts.

6. As the three of them look across the bay toward Daisy’s house, Nick tells us, “Possibly it
had occurred to him that the colossal significance of that light had now vanished forever.
Compared to that great distance that had separated him from Daisy it had seemed very near
to her, almost touching her. It had seemed as close as a star to the moon. Now it was again a
green light on a dock. His count of enchanted objects had diminished by one.” First, explain
what Fitzgerald means by “the great distance” between Gatsby and Daisy. Then, explain
the significance of the fact that the green light is now just a light on a dock and that Gatsby’s
“count of enchanted objects had diminished by one.”

The Great Gatsby, Ch. 5

1. What steps has Gatsby taken to ensure this reunion day is perfect?

2. What’s the weather like at the beginning of the chapter? Symbolically analyze this element of the scene.

3. Why does Gatsby take Nick and Daisy the long away around his house to the front door instead of just cutting through the
back lawn?

4. When Nick asks Gatsby what business he is in, Gatsby responds, “That’s my affair,” before he realizes that this is not an
appropriate reply. Why does Gatsby give that answer, and why is not it an appropriate reply?

5. Okay, let’s talk about that scene with the shirts. Obviously, Daisy’s not crying because of the
actual shirts. Analyze the passage and explain what, exactly, has caused Daisy to become so
emotional as she wraps herself in all those shirts.

6. As the three of them look across the bay toward Daisy’s house, Nick tells us, “Possibly it
had occurred to him that the colossal significance of that light had now vanished forever.
Compared to that great distance that had separated him from Daisy it had seemed very near
to her, almost touching her. It had seemed as close as a star to the moon. Now it was again a
green light on a dock. His count of enchanted objects had diminished by one.” First, explain
what Fitzgerald means by “the great distance” between Gatsby and Daisy. Then, explain
the significance of the fact that the green light is now just a light on a dock and that Gatsby’s
“count of enchanted objects had diminished by one.”
The Great Gatsby, Ch. 6
1. In the first few pages of this chapter, we learn about Gatsby’s background. When did James Gatz change his name to Jay
Gatsby? Why did he leave college after just two weeks?

2. Nick says, “So he [Gatsby] invented just the sort of Jay Gatsby that a seventeen-year-
old boy would be likely to invent, and to this conception he was faithful to the end.” For
James Gatz, what does he expect the future Jay Gatsby’s life will be like? Specifically, at
night, what sets James’ heart “in a constant, turbulent” riot?

3. To young Gatz, what does Dan Cody’s yacht represent?

4. Why does Gatsby not get the $25,000 left to him in Cody’s will? What lesson did
young Gatsby likely learn from this incident?

5. After crossing paths with Gatsby, Tom says, “I may be old-fashioned in my ideas, but
women run around too much these days to suit me.” What’s interesting (and hypocritical)
about this line?

6. What is Daisy’s opinion of Gatsby’s party?

7. While the reader can have easily predicted Daisy and Tom’s reactions to his party, Gatsby cannot. Why not?

8. What is Nick’s view of repeating the past, and what is Gatsby’s opinion? Why is Gatsby’s opinion unrealistic?

The Great Gatsby, Ch. 6

1. In the first few pages of this chapter, we learn about Gatsby’s background. When did James Gatz change his name to Jay
Gatsby? Why did he leave college after just two weeks?

2. Nick says, “So he [Gatsby] invented just the sort of Jay Gatsby that a seventeen-year-
old boy would be likely to invent, and to this conception he was faithful to the end.” For
James Gatz, what does he expect the future Jay Gatsby’s life will be like? Specifically, at
night, what sets James’ heart “in a constant, turbulent” riot?

3. To young Gatz, what does Dan Cody’s yacht represent?

4. Why does Gatsby not get the $25,000 left to him in Cody’s will? What lesson did
young Gatsby likely learn from this incident?

5. After crossing paths with Gatsby, Tom says, “I may be old-fashioned in my ideas, but
women run around too much these days to suit me.” What’s interesting (and hypocritical)
about this line?

6. What is Daisy’s opinion of Gatsby’s party?

7. While the reader can have easily predicted Daisy and Tom’s reactions to his party, Gatsby cannot. Why not?

8. What is Nick’s view of repeating the past, and what is Gatsby’s opinion? Why is Gatsby’s opinion unrealistic?
The Great Gatsby
Chapter 7
1. Why, do you suppose, Fitzgerald
links the behavior of the characters
to the hottest day of the summer?
10. Daisy says that Tom is
“revolting.” To what, can you
imagine, is she referring?

2. When Gatsby briefly meets 11. Why does Daisy have a tough
Daisy’s little girl, he is somewhat time saying, as Gatsby wishes, that
unnerved. Symbolically, what does she never loved Tom?
the little girl represent?
12. Why is it so important to Gatsby
3. What causes Tom to realize that that Daisy say she never loved Tom?
his wife has been having an affair
with Gatsby? 13. How has Gatsby earned most of
his money, and what does Tom say
4. What does Gatsby understand that startles Gatsby?
about Daisy’s voice that Nick does
not? 14. What is Daisy’s reaction to this
news?
5. Describe the driving arrangement
that brings the five characters into 15. Describe the hit-and-run scene.
the city.
16. Why does Tom make the point
6. Why, do you suppose, Tom to Wilson that he just drove the
decides to let Wilson finally have coupe from New York and the
the car he has been promising him? yellow car does not actually belong
to him?
7. What indication is there at this
point that, in Myrtle’s mind anyway, 17. What indication is there that Tom
Tom has been more than a fling? really was fond of Myrtle?

8. Besides Myrtle’s, what other eyes 18. What does the reader learn that
“kept their vigil” on the activities Tom does not know?
along the roadway?
19. What is the scene that Nick
9. As always, there is a grain of observes taking place between Tom
truth in what Gatsby says. In what and Daisy in the kitchen? Mint Julep
sense is he an Oxford man?
20. Why does this scene suggest ill
for Gatsby?
The Great Gatsby, Ch. 8
1. Why was the young Gatsby drawn to Daisy?

2. What is the cause of the problem between Jordan

and Nick?

3. In what context do Dr. Eckleburg’s eyes appear

in this chapter?

4. When Wilson disappears for three hours, where

do you guess he might have gone? (You won’t know
for certain until later.)

5. Gatsby asks the groundskeeper not to drain the

pool. Why? In light of what happens at the very end of
this chapter, how is this exchange symbolically meaningful?

6. How can Wilson’s actions at the end of this chapter be explained?

7. What were Nick’s final words to Gatsby? Why is this a fitting goodbye?

The Great Gatsby, Ch. 8

1. Why was the young Gatsby drawn to Daisy?

2. What is the cause of the problem between Jordan

and Nick?

3. In what context do Dr. Eckleburg’s eyes appear

in this chapter?

4. When Wilson disappears for three hours, where

do you guess he might have gone? (You won’t know
for certain until later.)

5. Gatsby asks the groundskeeper not to drain the

pool. Why? In light of what happens at the very end of
this chapter, how is this exchange symbolically meaningful?

6. How can Wilson’s actions at the end of this chapter be explained?

7. What were Nick’s final words to Gatsby? Why is this a fitting goodbye?
The Great Gatsby, Ch. 9
1. Why does Nick feel responsible for getting people to the funeral? Why do you suppose Wolfsheim reacts the
way he does?

2. What does young Jimmy Gatz’s daily schedule say about him?

3. Is Nick surprised that Daisy has not sent a message or flowers? Are
you?

4. Nick’s fantastic dream involves El Greco figures. What is the dream,

and what might this dream represent in regard to Nick’s present feelings
about the East?

5. What shocking piece of information does Nick receive in his chance

meeting with Tom? What is Nick’s final feeling about Tom and Daisy?

6. In the last four paragraphs, Nick makes the symbol of the green light very concrete. What does the green light
symbolize?

7. Keeping the last few paragraphs in mind, what does the last sentence in the story mean?

The Great Gatsby, Ch. 9

1. Why does Nick feel responsible for getting people to the funeral? Why do you suppose Wolfsheim reacts the
way he does?

2. What does young Jimmy Gatz’s daily schedule say about him?

3. Is Nick surprised that Daisy has not sent a message or flowers? Are
you?

4. Nick’s fantastic dream involves El Greco figures. What is the dream,

and what might this dream represent in regard to Nick’s present feelings
about the East?

5. What shocking piece of information does Nick receive in his chance

meeting with Tom? What is Nick’s final feeling about Tom and Daisy?

6. In the last four paragraphs, Nick makes the symbol of the green light very concrete. What does the green light
symbolize?

7. Keeping the last few paragraphs in mind, what does the last sentence in the story mean?
Chapter One
1. What was the advice given to Nick by his father? He reminded Nick that not everyone’s had all of the
advantages that he’s had and that he shouldn’t be judgmental of others. How, do you suppose, this makes him a
good person to tell this story? Since he’s open to people, non-judgmental, and a good listener, people are often
more open with him than with others. Because of this, he’s privy to information about people that they might not
normally share. Good listeners often have many good stories to tell.

2. What is Nick’s social class/background? He is upper-middle class. His family has money, but not at the level
of the Buchanan family. How did his family make its money? The family owns a cluster of hardware stores in the
midwest.

3. When Nick returns from the war, why does he decide to go East? He was uncertain what to do with himself and
figured there was opportunity on Wall Street.

4. How is West Egg different from East Egg? West Egg is where people with new money live. East Egg is where the
old money families live. Both are luxurious, but the East Eggers are seen as a higher class. West Eggers are wealthy,
but can be seen as being tacky with their wealth.

5. Before meeting him, what does Nick tell us about Tom Buchanan? They went to school together at Yale. Tom was
a football star at the college and comes from an extremely wealthy family. As an example of the excess his wealth
can buy, Nick tells us that Tom was able to purchase a “string of polo ponies from Lake Forest. “ Also, it seems that
Tom likely peaked in college, a depressing realization for a man’s life.

6. If you were going to pick one color to connect with Daisy Buchanan, what color would it be? White. Explain your
reasoning. She’s dressed in white, speaks of her “white” girlhood, and her name, “Daisy” evokes the classic white
flower.

7. We find out that Tom has “some woman in New York.” What unflattering feature of Jordan Baker’s personality is
revealed in this scene? She’s a gossip and seems to take a small amount of pleasure in Daisy’s pain in this scene.

8. What’s the name of the book that Tom wants to discuss at dinner? The book is called The Rise of the Colored
Empires by Goddard. What does this book’s content show us about Tom? Tom is a huge racist. We should be
troubled by this realization.

9. What is the reader left to think about Daisy’s emotional state and her relationship with Tom? Daisy is all over the
place, almost like a manic-depressive (up, down, all around) in this evening. She’s trying to pretend that everything’s
okay, but then she confesses her darkest marital woes to Nick, a cousin she really doesn’t know very well at all. Her
marriage with Tom is troubled. He’s having an affair with the woman on the phone tonight and he wasn’t even there
for the birth of their daughter. Tom’s a jerk, and Daisy’s a mess.

10. Who is Jordan Baker, and what has Nick heard about her? She is Daisy’s friend and a professional golfer. Nick
seems to remember she was involved in some unpleasantness connected to her sport, but he doesn’t remember the
details.

11. At the end of this chapter, Nick sees Gatsby on the lawn and is about to call to him and introduce himself, but
he does not. What stops Nick? Gatsby is all alone, reaching out to touch something across the dark waters. It seems
like he wants to be alone. What does Gatsby’s “trembling” suggest? There’s something out there that he’s yearning
to acquire. The trembling makes it seem like the thing is emotional and important.
12. The green light that Gatsby is staring at will become an important symbol in the book. What symbolic
associations do you connect to the color green? Answers will vary, but students will likely mention that green reminds
them of jealousy (i.e., green-eyed monster), money, and/or the earth.

Chapter Two
1. The description of the “valley of ashes” opens this chapter. Literally, what is the valley of ashes? It is the industrial
section that separates the fashionable West and East Eggs from Manhattan. It’s gray and covered in ashes/soot
from all of the factories in the area. Nick travels through the valley of ashes every day on the train he takes to work.
What might it represent on a symbolic level? Symbolically, this is a wasteland. The Wilsons’ garage is here and this
is where the sinful Myrtle lives. It’s colored gray, as the moral ambiguity of right and wrong is also in the reader’s
mind.

2. Compare and contrast George Wilson and Tom Buchanan. Then, compare and contrast Myrtle Wilson and Daisy
Buchanan. George is poor, gray, and a shadow of a man. His wife is cheating on him, but he doesn’t know. Tom
is wealthy and powerful. He’s making a fool of Wilson. Myrtle is full-bodied and sexy, while Daisy is thin and frail.
Myrtle, although we don’t like her, is living life fully and oozes sexuality. Daisy, unlike George, is fully aware of the
affair her husband is having, but she’s powerless to stop it.

3. How do we know that Myrtle Wilson is not an intellectual? Her manner of speech places her solidly in the
working class (ex: “I don’t suppose you got that kind?”) Also, she reads Town Tattle, a gossip magazine, and
salacious fiction like Simon Called Peter. She’s not a deep thinker.

4. Notice how often and in what context Doctor Eckleburg’s eyes are mentioned. Symbolically, what might those
eyes on that billboard represent? The eyes on the billboard are like the eyes of God, watching over the sinful acts
of the people who live in the shadow of the sign. Two large, disembodied eyeballs glare down over the area. It’s
creepy, really.

5. What’s up with the puppy? Why do you suppose Fitzgerald included it as an element in this chapter? Myrtle has
Tom buy the dog for her on a whim. The puppy symbolizes the lack of thought with which Myrtle and Tom are living
their lives/committing their sins. There’s no long-term thought here about the consequences of the choices they make.
If they want something, they get it (or do it); the puppy serves as a reminder that living things (people?) will suffer
when we act without thought or without a plan.

6. Do you think Tom will leave Daisy for Myrtle? Support your answer. Tom will never leave Daisy for Myrtle. He
breaks Myrtle’s nose when she gets mouthy and says his wife’s name. Myrtle is beneath Tom in social class and,
while it’s fine to have an affair with Myrtle, he would never, ever marry her. It’d be a scandal and he doesn’t love
her; he tolerates her so the affair can continue.

Chapter Three
1. Nick describes the people who attend Gatsby’s parties and says “that once there, the guests conducted
themselves according to the rules of behavior associated with amusement parks.” Given this, what can you conclude
is Nick’s opinion of Gatsby’s party guests? He is not impressed. All of these fancy people behave like drunken fools.
Nick isn’t a big drinker, and it’s not much fun to hang out with a bunch of drunks when you’re the only sober one
around.

2. Why does Jordan want to leave the group from East Egg? She’s bored with the group and there’s a young man
serving as her escort who has been coming on too strong. Why does Nick want to leave the group? He wants to
meet Gatsby. He was one of the few people who was actually invited to the party and he wants to meet the host/his
neighbor.

3. Who is Owl-Eyes? A middle-aged drunk man sitting in Gatsby’s library as he tries to sober up a bit. What
surprises him about Gatsby’s library? He is stunned that the books in Gatsby’s massive library are real. Why would
this impress him? In West Egg, it’s common to find that things have been built merely for show, but that they are
actually a facade. He expected the books to be fake ones, or just blank books, so he’s impressed to realize that
Gatsby has gone to great expense to furnish a real library. It’s sort of like modern homes that are built with marble
columns, but you find out later that the columns are actually hollow and faux painted. Symbolically, the library
connects to Gatsby himself as your students will soon realize that he’s a fraud, too.

4. What unexpected common bond do Gatsby and Nick share? They fought in similar battalions during World War
I and Gatsby recognizes Nick – quite the coincidence!

5. Nick says, “I was looking at an elegant young roughneck...whose elaborate formality of speech just missed being
absurd. Some time before he introduced himself I’d got a strong impression that he was picking his words with care.”
What is Fitzgerald trying to convey here about Gatsby? The author is trying to make us see that Gatsby is putting on
a bit of a show. How should we feel about Gatsby here? He’s not all he seems to be and we should be a bit wary
of fully trusting him. We like him and are impressed by his generosity in throwing such parties, but we’re also a bit
skeptical about his background.

6. Why do you suppose that Jordan does not believe Gatsby when he says that he had attended Oxford College
in England? The way he explains it to people make us all think that he’s trying too hard to impress. Also, Jordan is a
huge liar and, well, it takes one to know one, right?

7. In what ways is Gatsby’s behavior at his party quite unlike the behavior of most of his guests? He doesn’t drink
and he holds to strict formality. He’s removed from the raucous fun.

8. Toward the end of the party, we have the unflattering description of husbands and wives and also the drunk who
has crashed his car. What is Fitzgerald’s deeper message to us here? There’s several potential answers here. First,
he may just be showing how poorly people behave when they’re drunk. Second, he might be showing that drunken
parties are the great leveler; people from both West Egg and East Egg illegally drink to excess. Finally, he could be
hinting that there will always be a price to pay for over-indulging. Literally, these people will have bruised marriages
and broken cars; figuratively, the wheels are falling off the forward motion of the country. The Roaring Twenties will,
of course, lead to the hangover of the Dirty Thirties/the Great Depression.

9. Jordan declares to Nick that she “hates careless people.” Explain the irony here. Jordan is about as careless/
irresponsible as they come. She cheats, lies, and accidentally destroys other people’s property (the convertible) all
without taking any sort of responsibility. She is exactly what she says she hates.

Chapter Four
1. Looking through the list of party-goers, find and paraphrase at least three pieces of evidence that the old money
is in East Egg and the new money in West Egg? 1. The East Eggers named Blackbuck are snooty and flip their noses
up at everyone. 2. East Eggers include legendary American family names, such as Voltaire and Stonewall Jackson,
and people Nick knew from Yale. 3. West Eggers are mostly movie/entertainment producers and people with more-
ethnic-sounding names like Poles and Mulreadys, making us think more of an immigrant class of people.
2. What is weird about Nick’s drive into New York with Gatsby? List at least three things about Gatsby in this
scene that strike you as odd. It’s an awkward drive, as Gatsby is trying way too hard to impress Nick. First, Gatsby
overshares about his background, being sure to mention that he inherited family money, but that all of his people
are dead now. Weird. Second, he emphasizes that he was “educated at Oxford,” in such a way that it immediately
makes Nick think that he’s lying. He’s even carrying around a photo of himself at Oxford to use as proof. Even
weirder. Third, he says his people are from the mid-west, but then says they’re from San Francisco. It doesn’t take a
geography expert to know that San Francisco is not in the mid-west. More weirdness. Finally (yes, here’s an extra
one for you), he’s carrying around a medal of valor from Montenegro. Who does that? Someone who’s trying too
hard to impress others, that’s who.

3. What two things does Nick see on/near the Queensboro Bridge that make him think that Gatsby is, perhaps,
telling the truth? There’s a somber funeral procession, but then they are passed by a limousine driven by a white
chauffeur. Inside the limo, two African-American men and a woman are having a riotous time. This contrast makes
Nick think that anything is possible in New York.

4. Who is Meyer Wolfsheim, and what do we know about him? Wolfsheim is a shady businessman/gangster who
Gatsby does business with. We know that he wears cufflinks made out of human molars (ew!) and that he was
involved in the scandalous fixing of the 1919 World Series.

5. Gatsby disappears when which other character unexpectedly arrives at lunch? Tom Buchanan. Take a guess as to
why Gatsby doesn’t want to see this character. It’s likely obvious to your class at this point in the story that Gatsby is
in love with Daisy or at least that he has a compelling reason to want to avoid Tom Buchanan.

6. Jordan recalls the time in 1917 when she saw Gatsby and Daisy together. From Jordan’s description, do you think
Daisy was genuinely interested in Gatsby? Yes. She’s so captivated by him in that scene that she doesn’t even notice
Jordan until she’s just five feet away. Daisy and Gatsby were very into each other back in the day.

7. How does Daisy behave the night before her wedding? She gets roaring drunk and attempts to throw away an
expensive pearl necklace that Tom gave her. Why? She’s having second thoughts about marrying Tom and has
received a letter that has caused her to become very upset.

8. Who, do you suppose, sent the letter that caused Daisy to become so upset? Gatsby. What do you think the letter
may have said? He was probably declaring his love for her in the letter.

9. Nick says, “Then it had not been merely the stars to which he had aspired on that June night” when Nick first
spotted Gatsby reaching out across the bay. What does Nick now realize about that night and about Gatsby’s real
estate purchase? Gatsby wants Daisy, but he also aspires to reach the higher social class that Daisy represents. Nick
realizes that Gatsby purchased that particular house because it’s adjacent to the Buchanans’ house.

10. What’s happening between Nick and Jordan? Nick is attracted to her, even if she doesn’t really like/respect
her. They have a romance brewing, but it’s more of a summer fling than the real thing.

Chapter Five
1. What steps has Gatsby taken to ensure this reunion day is perfect? He’s had way too many flowers delivered,
had Nick’s lawn mowed, and is wearing a white suit with silver shirt and gold tie.

2. What’s the weather like at the beginning of the chapter? It’s raining. Symbolically analyze this element of the
scene. Analysis of the rain could go two different ways. First, it might be a sign that nothing can ever be perfect, no
matter how much Gatsby wants it to be. Second, it might be an optimistic sign of renewal and cleanliness, washing
away the sorrow of the past.

3. Why does Gatsby take Nick and Daisy the long away around his house to the front door instead of just cutting
through the back lawn? He wants to show off his impressive home by giving the full, grand tour. It’s important for
Daisy to get the full picture of his wealth.

4. When Nick asks Gatsby what business he is in, Gatsby responds, “That’s my affair,” before he realizes that this is
not an appropriate reply. Why does Gatsby give that answer, and why is not it an appropriate reply? He gives the
answer because he’s up to no good (working as a bootlegger) and doesn’t want Daisy, or anyone, to know about
it. This is not an appropriate respond because it’s curt and rude.

5. Okay, let’s talk about that scene with the shirts. Obviously, Daisy’s not crying because of the actual shirts.
Analyze the passage and explain what, exactly, has caused Daisy to become so emotional as she wraps herself
in all those fancy shirts. The beautiful, colorful shirts are a symbol of what Daisy’s lost by marrying Tom. Gatsby is
the colorful, exotic fabric, while Tom would be the staid, starched white shirts worn by the upper-class. All of the
color and fun is out of her lily-white life. Daisy is the ultimate material girl, so it’s no surprise that the fine material of
Gatsby’s shirt bring her to the edge of her breaking point. If the clothes make the man, Daisy is likely wishing that
she could wrap herself up in Gatsby. The shirts will have to do – for now.

6. As the three of them look across the bay toward Daisy’s house, Nick tells us, “Possibly it had occurred to him that
the colossal significance of that light had now vanished forever. Compared to that great distance that had separated
him from Daisy it had seemed very near to her, almost touching her. It had seemed as close as a star to the moon.
Now it was again a green light on a dock. His count of enchanted objects had diminished by one.” First, explain
what Fitzgerald means by “the great distance” between Gatsby and Daisy. They’re apart because of her marriage
to Tom, but, more importantly, the distance between them is a huge one of social class. He’s trying to reach out and
close the gap between their social classes, but, of course, that is impossible. Then, explain the significance of the
fact that the green light is now just a light on a dock and that Gatsby’s “count of enchanted objects had diminished
by one.” This part of the reunion is like the feeling you get once you finally accomplish a goal/obtain something
you’ve wanted for a long time. While you’re happy to finally have that thing, there might be a little bit of a let-
down because the item/achievement isn’t as awesome as you’d always dreamed it would be. This reminds me of
young brides who spend a year planning their wedding and then don’t even enjoy their big day because they’re
so exhausted and/or pained about making sure every detail is absolutely perfect. They’re bound to be let down, at
least a little. This is what’s happening to Gatsby at the end of this chapter.

Chapter Six
1. In the first few pages of this chapter, we learn about Gatsby’s background. When did James Gatz change his
name to Jay Gatsby? He changed his name when he was 17. Why did he leave college after just two weeks? He
was frustrated that the people there didn’t immediately recognize his greatness and he felt the janitor work-study job
he was given was beneath him.

2. Nick says, “So he [Gatsby] invented just the sort of Jay Gatsby that a seventeen-year-old boy would be likely
to invent, and to this conception he was faithful to the end.” For James Gatz, what does he expect the future Jay
Gatsby’s life will be like? His new life will be filled with every luxury. All of his dreams will come true. Specifically, at
night, what sets James’ heart “in a constant, turbulent” riot? His desires for bigger, more gaudy displays of wealth.
As a young man, he figures glitz and bling are true symbols of wealth. He has a young, North Dakota sense of what
an elite wealthy life would be like; the bigger/the gaudier, the better, he thinks.
3. To young Gatz, what does Dan Cody’s yacht represent? The yacht represents all of the beauty and glamour in
the world.

4. Why does Gatsby not get the $25,000 left to him in Cody’s will? Through legal wranglings that Gatsby does
not understand, Ella Kaye is able to make sure Gatsby doesn’t get the money. What lesson did young Gatsby likely
learn from this incident? He learned that he couldn’t rely on wealth to be given to him; he would have to earn it
himself.

5. After crossing paths with Gatsby, Tom says, “I may be old-fashioned in my ideas, but women run around too much
these days to suit me.” What’s interesting (and hypocritical) about this line? Obviously, Tom is a hypocrite because
he’s done plenty of running around himself and he’s attracted to women, like Myrtle, who are exactly the kind of
women he’s talking about here.

6. What is Daisy’s opinion of Gatsby’s party? She pretends to like it, but she doesn’t really. The people are loud,
drunk, and obnoxious. Although the party is ritzy and luxurious, there’s really nothing classy about it.

7. While the reader can have easily predicted Daisy and Tom’s reactions to his party, Gatsby cannot. Why not? He
doesn’t understand what is truly appealing to the elite class. He still operates under that vision of wealth/luxury that
he conjured for himself when he was 17. His vision of having “made it” is the new money vision of success (grand,
opulent, over-the-top), but the old money ways are far more understated and refined.

8. What is Nick’s view of repeating the past, and what is Gatsby’s opinion? Nick says you can’t repeat the past,
that you must move on. Gatsby disagrees; he’s determined to repeat the past and wants to pick up with Daisy
right where they left off five years ago. Why is Gatsby’s opinion unrealistic? Obviously, people change and
life’s circumstances change. Daisy isn’t the same girl she was back in Louisville. Now, she has a daughter and a
complicated marriage with Tom. You really can’t go back again.

Chapter Seven
1. Why, do you suppose, Fitzgerald links the behavior of the characters to the hottest day of the summer? Fitzgerald
has the weather mirror the growing heat/tension among the characters in the love triangle. Things are hot and
miserable. This use of weather foreshadows the blow-up at the hotel room.

2. When Gatsby briefly meets Daisy’s little girl, he is somewhat unnerved. Symbolically, what does the little girl
represent? The girl is physical evidence that he cannot repeat the past. He can’t erase the fact that Daisy now has
a daughter. The girl doesn’t fit into Gatsby’s view of his future with Daisy; she’s evidence that proves Nick is right
about being unable to relive the past.

3. What causes Tom to realize that his wife has been having an affair with Gatsby? Tom can read between the lines
as Daisy is fawning over Gatsby. He can tell from the tone of her voice, which is not discreet.

4. What does Gatsby understand about Daisy’s voice that Nick does not? He knows that part of her voice’s allure is
that it sounds like money, like gold coins jingling.

5. Describe the driving arrangement that brings the five characters into the city. Daisy and Gatsby drive together in
Tom’s car, while Tom drives Nick and Jordan in Gatsby’s car.

6. Why, do you suppose, Tom decides to let Wilson finally have the car he has been promising him? He feels slightly
uncomfortable when he has to face the pain that the affair has caused Wilson. If Wilson’s planning on taking Myrtle
out west, then Tom must figure one last deal on a car is something he owes to the poor man he’s turned into a
cuckold.

7. What indication is there at this point that, in Myrtle’s mind anyway, Tom has been more than a fling? Myrtle has
refused to move away with husband. Clearly, she wants to stay in New York because she imagines she’ll have some
sort of future with Tom.

8. Besides Myrtle’s, what other eyes “kept their vigil” on the activities along the roadway? Doctor T. J. Eckleburg’s
eyes from the billboard are also watching everyone.

9. As always, there is a grain of truth in what Gatsby says. In what sense is he an Oxford man? He participated
in a study abroad program for soldiers after the war. He attended some classes at Oxford, but was there only five
months.

10. Daisy says that Tom is “revolting.” To what, can you imagine, is she referring? He says that he loves her, but
admits that he sometimes goes “off on a spree” and has an affair. He’s admitting to his infidelity in the same breath
that he says he loves her.

11. Why does Daisy have a tough time saying, as Gatsby wishes, that she never loved Tom? Even though it goes
against Gatsby’s wish, there was a time when Daisy loved Tom. She can’t erase the fact that they had some good
times.

12. Why is it so important to Gatsby that Daisy say she never loved Tom? In order for his fantasy to be complete, he
needs to hear that her love for him was pure, that she could never love another man. This isn’t true, of course, just as
the dream that Gatsby has cannot be achieved.

13. How has Gatsby earned most of his money, and what does Tom say that startles Gatsby? Gatsby has illegally
earned his money by bootlegging and having shady business operations. Tom startles Gatsby when he knows that
Gatsby is up to a bigger score, something of which Tom’s contact Walter doesn’t know the details.

14. What is Daisy’s reaction to this news? She’s terrified and then pulls back from Gatsby. Eventually, she begs Tom
to stop talking and attacking Gatsby. She wants to go home.

15. Describe the hit-and-run scene. Myrtle, who’s been locked up by her husband, spots the flashy yellow car that
she saw Tom driving earlier in the day. She breaks out of her home and runs into the street, trying to flag down Tom,
but not realizing that Tom isn’t in that car. The car, driven by Daisy, mows down Myrtle and then leaves the scene of
the accident. Later, Gatsby tells Nick that Daisy was driving, but that he’ll take the blame in order to protect her.

16. Why does Tom make the point to Wilson that he just drove the coupe from New York and the yellow car does
not actually belong to him? He knows that Wilson saw him driving the very same car earlier that afternoon and he
wants to remove any suspicion that may fall on him.

17. What indication is there that Tom really was fond of Myrtle? When he realizes that Myrtle’s been hurt, there’s a
“harsh sound in his throat” and he pushes his way toward the front of the crowd to see her.

18. What does the reader learn that Tom does not know? We know that Daisy, not Gatsby, was the driver of the car
that hit Myrtle.

19. What is the scene that Nick observes taking place between Tom and Daisy in the kitchen? They are talking
together at a table, with cold chicken and a couple of bottles of ale between them. Tom is talking, Daisy’s nodding
in agreement, and Tom’s big hand wraps over Daisy’s hands. It’s clear to Nick that they’re conspiring together.

20. Why does this scene suggest ill for Gatsby? Tom has won. Daisy will follow Tom and do as he says. She wants
to be saved from this situation and Tom, not Gatsby, is the man she’ll look to for rescue.

Chapter Eight
1. Why was the young Gatsby drawn to Daisy? He liked that other men wanted her and he also like the glamour of
her house.

2. What is the cause of the problem between Jordan and Nick? After witnessing everything from the previous day,
any connection or romance seems dead now. They never really liked each other that much, anyway, so it’s not a big
loss for either when they fail to connect.

3. In what context do Dr. Eckleburg’s eyes appear in this chapter? Wilson believes the billboard’s eyes are literally
the eyes of God and that God has seen and judged the sinful acts of the people in the valley of the ashes.

4. When Wilson disappears for three hours, where do you guess he might have gone? (You won’t know for
certain until later.) Answers will vary, but we know later that Wilson went to Tom’s house to find out about the owner
of the yellow car. We’ll find out in the final chapter that Tom tells a deranged-looking Wilson where Gatsby lives.

5. Gatsby asks the groundskeeper not to drain the pool. Why? He realizes that the entire summer season has
passed and he hasn’t once taken a swim in his own pool. He decides today is the day to take a swim while he
waits for Daisy’s call. In light of what happens at the very end of this chapter, how is this exchange symbolically
meaningful? Summer is officially over, but Gatsby just can’t let go. He wants to live in the past, not accepting the
change of time, change of seasons. He’s lost Daisy, but he’s still delusionally waiting to hear from her.

6. How can Wilson’s actions at the end of this chapter be explained? He mistakenly believes that Gatsby is the one
who killed his wife, so he hunts him down and shoots him. Wilson, unable to face the horror of what he’s done, then
turns the gun on himself.

7. What were Nick’s final words to Gatsby? Nick said, “They’re a rotten crowd. You’re worth the whole damn bunch
put together.” Why is this a fitting goodbye? It’s true. The irony, of course, is that Gatsby wanted so desperately to
be a part of this elite group that is actually filled with selfish, lousy people.

Chapter Nine
1. Why does Nick feel responsible for getting people to the funeral? He thought of himself as Gatsby’s friend and he
wants to do the right thing. Why do you suppose Wolfsheim reacts the way he does? He wants to distance himself
from anything that would draw attention to himself. He’s a gangster and needs to keep things on the down-low.

2. What does young Jimmy Gatz’s daily schedule say about him? He was an extremely hard worker and dedicated
to self-improvement, though he was frustrated by his lapses in self-discipline.

3. Is Nick surprised that Daisy has not sent a message or flowers? He’s not really surprised and says that he
understands her position and doesn’t resent her; however, the fact that he mentions it while talking about the funeral
does make it seem like he’s disappointed that Daisy didn’t come to give her regards. Are you? No, not at all. Daisy
is a selfish woman who’s already headed out of town to save her own neck.
4. Nick’s fantastic dream involves El Greco figures. What is the dream, and what might this dream represent in
regard to Nick’s present feelings about the East? The dream was a glitzy scene of West Egg partiers as they carried
a drunken woman dripping with jewels into the wrong house, but no one knows the woman or cares about her. A
darker read on the description is that the woman is dead. The dream means that the East Coast has lost the allure it
once held. The consequence of this lifestyle is human carnage. No amount of glitz or bling can cover the darkness
and sorrow.

5. What shocking piece of information does Nick receive in his chance meeting with Tom? He learns that Tom was
the person who told Wilson that Gatsby was the man who killed Myrtle. What is Nick’s final feeling about Tom and
Daisy? That they are careless people who create damage/messes and expect other people to clean up the mess.
They are able to use their money and their influence to avoid taking responsibility for the damage they cause.

6. In the last four paragraphs, Nick makes the symbol of the green light very concrete. What does the green light
symbolize? Nick connects the green light to the lush green continent of America as viewed by early settlers. Just as
Gatsby was reaching for the promise of a higher social level, so to were the early Dutch settlers looking for a better,
more satisfying life promised by this new land.

7. Keeping the last few paragraphs in mind, what does the last sentence in the story mean? It’s a depressing line
because it seems we are doomed to forever try to move forward by rowing against a strong current that forever
pushes up backward. We keep reaching for the wonderful picture of the future, but we’ll never be able to reach it,
Fitzgerald seems to be saying here. Bleak stuff.