The Great Gatsby
Discussion Questions
Chapter 1
Tom & Daisy Buchanan: First Impressions
1. When Nick Carraway travels to East Egg to visit Tom
and Daisy, he is given a tour of their house by Tom.
How does Tom conduct this house tour? What do
Tom’s words about his house, or his treatment of his
guest, reveal about his personality? How might Tom
embody a certain type of masculinity?
2. When readers are introduced to Daisy, she is described
as reclining on a couch in the middle of a room where
a breeze blows in from the windows, causing the
curtains and the women’s dresses to flutter freely.
How might Fitzgerald’s description of this room
contribute to his portrait of the main female character,
Daisy? How do literary devices like imagery and
figurative language contribute to the way Fitzgerald
characterizes her? Finally, does Tom’s act of shutting
the windows reveal anything about how his
personality differs from Daisy’s personality?
Tom Buchanan: White Supremacist?
3. After the guests sit down for dinner on the Buchanan
porch, Tom announces that he’s been reading a book
called “The Rise of the Colored
Empires.” Anyone reading The Great Gatsby in the 1920’s would have recognized the
title of the book as a thinly veiled reference to an actual book: The Rising Tide of Color:
The Threat Against White World-Supremacy by Lothrop Stoddard (1920). Stoddard’s
book incited a wave of racism that swept through the U.S. in the 1920’s. What does
Tom’s fondness for the made-up version of this book reveal about his personality? Why
might Tom feel threatened by the alleged “rise”? How are readers of Fitzgerald’s novel
supposed to feel about Tom’s enthusiasm for the book?
4. How does Daisy respond when Tom announces that he has been reading the book
and expresses his concern that the “rise” is going to leave white people “utterly
submerged”? Does Daisy share her husband’s worldview? What evidence supports your
answer?
Moskovian: AP Language 1
Daisy Buchanan: Liberated or Trapped?
5. The dinner party gets interrupted by a phone call. How does the call affect each character’s mood? When the
phone rings for a second time and Tom goes inside, Daisy takes Nick to the front porch where they talk in
private. Does the tone of Daisy’s voice change when talking to Nick in private? As she confides in Nick about
how Tom wasn’t present when their daughter was born, what do these scenes reveal about Tom, Daisy, and
their marriage?
6. Why might Daisy hope for her daughter “a fool”? Why does she feel that that’s the “best thing” a girl can be?
Modern America: Restlessness & Romantic Promises
7. Nick observes that after he returned home from WWI, he experienced a feeling of “restless[ness]” that caused
him to move to New York City. He describes Tom and Daisy as being similarly afflicted by a type of
restlessness. Why are so many of the characters in the novel described as being this way? How might the
experience of being a soldier have contributed to this feeling? How might the conditions of during the 20’s
have exacerbated these feelings?
Gatsby: Man of Mystery?
8. In the chapters last two pages, we are introduced, although briefly, to
Gatsby. He is said to appear suddenly and vanish instantly. Why might
Fitzgerald choose to associate Gatsby with words like “figure,” “shadow,”
and “vanish”? What connotations are suggested by Fitzgeradl’s diction?
Moskovian: AP Language 2
Chapter 2
The Valley of Ashes
1. The setting for chapter 2 is an impoverished
area called the Valley of Ashes. How does the
narrator describe the valley? How do imagery
and figurative language contribute to the
portrayal of this area?
2. As Nick is riding on a train through the
Valley of Ashes, he looks out the window and
sees the billboard with the enormous “eyes of
Dr. T.J. Eckleburg.” Why might Fitzgerald
choose to position such a symbol above an
ash-covered industrial “waste land” where
working-class people like the WIlsons are
forced to live and work? How might he use
the billboard to deliver a subtle message
about life in the modern age?
Myrtle Wilson
3. After Myrtle asks whether the salesman has any police dogs, the salesman pulls a brown dog out of his basket
and holds it up, provoking Tom to say, “That’s no police dog.” What might Tom’s comment about the dog’s
breed reveal about his values? When the salesman places the puppy into Myrtle’s lap, she asks, “Is it a boy or
a girl?” Does this question remind you of any previous scenes from the novel so far? How might this parallel
be significant?
4. The magazines on Myrtle’s coffee table reveal a lot about her
interests and values. They include tabloid magazines like Town Tattle and
several other social magazines. What do these magazines reveal about
Myrtle’s aesthetic tastes? What do they reveal about her class position?
5. Beginning in chapter 2, the clothes worn by various characters
become an important theme. What does Myrtle wear in this chapter? How
do her clothes influence how she behaves?
Moskovian: AP Language 3
Tom’s Affair
1. Do Tom and Myrtle share the same understanding of the nature of their
relationship? Does Tom want a permanent relationship with her, or does he
merely view her as a temporary satisfaction? Does Myrtle believe that her
relationship with Tom will amount to a permanent ticket into his world of
old money? Or is she merely exploiting him in order to satisfy her material
desires? Who would you describe as holding the power in their relationship?
Who is taking advantage the most of who?
2. What do you make of Tom’s assertion, as told by Myrtle’s sister, that he’s
unable to divorce Daisy because “his wife [is] keeping them apart.” If Tom
doesn’t intend to divorce Daisy and marry Myrle, why would he decide to
flaunt his affair with her? What do his words and actions reveal about his
personality?
Chapter 3
Gatsby’s Party
1. How does the narrator describe the ambiance at Gatsby’s
party? How do the guests behave themselves? Finally,
how does the party that Gatsby hosts in this chapter differ
from the dinner party that the Buchanans host in chapter
1?
2. Jordan Baker comes to Gatsby’s party with a group of
“three married couples” who are from East Egg. How do
the people from East Egg behave themselves at a party
that takes place in West Egg? What might their behavior
reveal about relations between East Egg and West Egg?
3. It’s not until the third chapter that Nick meets Gatsby.
When they finally meet, Nick is unaware that he’s talking
to his host. Why might Fitzgerald wait so long to
introduce the title character? Shortly after Nick meets
Gatsby, Gatsby has to take a phone call. What is the
significance of his disappearance? Does it recall scenes
from other chapters?
4. Throughout chapter 3, Nick portrays Gatsby as a solitary
figure. In the middle of the party, Nick sees Gatsby “standing along on the marble steps and looking from one
group to another with approving eyes.” What is the significance of this? What might it reveal about Gatsby,
his priorities, and his intentions?
Moskovian: AP Language 4
5. When Nick and Jordan enter Gatsby’s library, a character named Owl Eyes is
amazed to find that the books are real. What had he expected to find instead? What
might the pages in Gatsby’s books reveal about the purpose of his library? Finally,
why might Nick give the nickname “Owl Eyes” to the character? How might this
name be revealing?
6. As Nick is leaving Gatsby’s party,
he encounters a car (a “new coupe”) that
has veered into the ditch and lost a wheel.
When the driver finally opens the door, he
seems incapable of comprehending that he may have been
responsible for driving the car off the road. What might Fitzgerald
be trying to suggest about how people in the 1920’s were adapting
to this new technology? Why might Fitzgerald refer to the car’s
detached tire as an “amputated wheel”?
Chapter 4
Driving to Manhattan
1. On a morning in late July, Gatsby drives his
Rolls Royce over to Nick’s house and honks
its “three-noted horn.” Consider the way Nick
describes Gatsby’s car. What might Gatsby’s
car reveal about his taste or his social
position?
2. When Gatsby and Nick are driving into
Manhattan, their car is slowed by a policeman
who threatens to give them a speeding ticket
until the policeman recognizes Gatsby and
apologizes. What does this incident reveal
about Gatsby? What does this incident reveal
about money and power?
3. While driving to Manhattan, Gatsby tells Nick the story of his past: that he is the son of wealthy parents from
the midwest, educated at Oxford, decorated in the war, and a traveler of Europe. Why does Gatsby feel
compelled to tell Nick this story? What details make his account seem rehearsed or artificial? How does
Fitzgerald create doubt about Gatsby’s credibility?
4. Gatsby produces tangible “proof” of his past, a medal from Montenegro and a photograph from Oxford. Why
might Fitzgerald include physical evidence? Does this make Gatsby more believable, or does it deepen the
mystery? What does this suggest about the relationship between appearance and truth in the novel?
Moskovian: AP Language 5
Meyer Wolfsheim: The Criminal Underworld
5. In Manhattan, Gatsby introduces Nick to Meyer
Wolfsheim, a man rumored to have fixed the 1919
World Series. Why might Fitzgerald connect Gatsby
to organized crime? What does Wolfsheim’s
presence suggest about the origins of Gatsby’s
wealth? How does this complicate the idea of the
American Dream?
6. Wolfsheim is described in exaggerated physical
detail (his cuff buttons made of human molars, for
example). How does Fitzgerald’s description shape
our impression of him? Why might Fitzgerald use such grotesque imagery here?
Jordan’s Story: Gatsby & Daisy’s Past
7. Jordan reveals that Gatsby and Daisy were once in love
before Gatsby went to war. Why does Gatsby want
Nick’s help in reuniting with Daisy instead of
approaching her directly? What does this suggest about
Gatsby’s personality and emotional vulnerability? Is
Gatsby driven by love, obsession, ambition, nostalgia, or
all of these?
8. Chapter 4 ends with Gatsby’s request that Nick invite
Daisy over for tea. Why is this seemingly simple request
treated with such suspense? How does Fitzgerald build
anticipation for their reunion?
Moskovian: AP Language 6
Chapter 5
The Reunion
1. When Gatsby and Daisy reunite at Nick’s house, Gatsby appears nervous
and awkward — even nearly knocking over a clock. Why is Gatsby so
anxious? What might the clock symbolize at this moment?
Additionally, how does Fitzgerald use weather imagery to mirror Gatsby’s
emotional state? What is the significance of the sunshine that appears later
in the scene?
2. When Gatsby shows Daisy his mansion, he displays his wealth
extravagantly, especially his collection of shirts. Why does Daisy cry over
the shirts? What does this moment reveal about Daisy’s values? What do we
see about Gatsby’s understanding of love?
3. As the chapter ends, Nick observes that Gatsby’s “count of enchanted objects had diminished by one.” What
does this mean? Has Gatsby’s dream grown stronger or weaker now that Daisy is physically present?
Chapter 6
Reinventing the Self
1. Chapter 6 reveals a lot about Gatsby’s past, namely that he was born James Gatz. Why is this information
withheld until now? How does the timing affect our understanding of his character? Consider the fact that
Gatsby rejects his parents as “shiftless and unsuccessful farm people.” What does this reveal about his attitude
toward class and identity? How might Gatsby embody the idea of self-invention?
Gatsby’s Party
1. Tom attends one of Gatsby’s parties and is visibly uncomfortable. How does Tom’s reaction differ from Nick’s
earlier impressions of Gatsby? What might Tom’s discomfort reveal about tensions between “old money” and
“new money”?
2. After the party, Gatsby is disappointed because Daisy did not enjoy herself. Why does Gatsby insist that he
can “repeat the past”? What does this statement reveal about his understanding of time and reality?
Additionally, consider the fact that Nick responds to Gatsby with, “You can’t repeat the past.” Who is right —
Nick or Gatsby?
Moskovian: AP Language 7
Chapter 7
The Confrontation
1. During the confrontation at the Plaza
Hotel, Gatsby demands that Daisy
declare she never loved Tom. Why is this
demand unreasonable? What does it
reveal about Gatsby’s idealized vision of
Daisy?
2. During their argument, Tom exposes
Gatsby’s criminal connections. How does
this revelation shift the power dynamic in
the room? Who “wins” the
confrontation? As you formulate your
response to this question, consider the speaker, his argument, his appeals, and any other choices he makes in
order to fulfill his purpose.
3. On their way back to East Egg, after a heated confrontation at the Plaza, Myrtle Wilson is struck and killed by
Gatsby’s yellow car, even though Daisy is the one driving. Why is it significant that Daisy is behind the
wheel? What does this reveal about Daisy’s character, her relationship to power, and her position within the
social hierarchy? Furthermore, why does Gatsby immediately agree to take the blame for the accident? What
does this decision suggest about the nature of his love for Daisy? In what ways does this moment mark the
beginning of the collapse of Gatsby’s dream?
Chapter 8
Revelations & the Death of the Dream
1. Gatsby waits outside Daisy’s house all night after Myrtle’s death, convinced she may need protection. What
does this behavior reveal about Gatsby’s emotional state and his understanding of Daisy? Is this moment
heroic, tragic, naive, or delusional? How does Fitzgerald create dramatic irony in this scene, especially when
contrasted with what Tom and Daisy are actually doing inside the house?
2. Gatsby finally tells Nick the full story of his early relationship with Daisy, admitting that he allowed her to
believe he came from wealth. How does this confession complicate the idea that Gatsby’s love is pure or
incorruptible? To what extent is Gatsby in love with Daisy herself, and to what extent is he in love with what
she represents (status, security, validation, or the fulfillment of his self-made identity)? How does Fitzgerald
use this backstory to further explore the tension between authenticity and performance in the novel?
Moskovian: AP Language 8
3. The eyes of Dr. T.J. Eckleburg reappear when George Wilson
interprets them as the eyes of God. How does this reinterpretation shift
the meaning of the symbol? How does George’s desperation contrast with
the carelessness of characters like Tom and Daisy? Also consider how
eyes are a recurring motif in the novel and what they might represent.
4. Gatsby’s death occurs in his swimming pool, a place associated
with luxury and leisure as well as a central location for his parties. Why
might Fitzgerald choose this setting for Gatsby’s final moments? How
does Gatsby’s death represent not only the end of a life, but the collapse
of an ideal? In what ways does his death symbolize the destruction of the American Dream as Fitzgerald
portrays it?
Chapter 9
The Aftermath
1. Despite hosting extravagant parties attended by hundreds, hardly anyone attends Gatsby’s funeral. Why do so
few people come? What does this reveal about the moral emptiness or superficiality of the society Fitzgerald
portrays? How does this moment force readers to reevaluate the significance of Gatsby’s popularity? Also,
consider the overall message Fitzgerald is trying to communicate through this.
2. In the final pages, Nick reflects on Gatsby’s dream in relation to the early Dutch sailors who first arrived in
America: “...I became aware of the old island here that flowered once for Dutch sailors’ eyes––a fresh, green
breast of the new world.” Why does Fitzgerald broaden the novel’s scope to include American history itself?
How does this comparison deepen the novel’s message on ambition, hope, and the American Dream?
3. The novel ends with the line “So we beat on, boats against the current, borne back ceaselessly into the past.”
How does this metaphor capture the novel’s central conflict between aspiration and memory, progress and
nostalgia? Does the ending suggest that striving is noble, futile, or both? How might this final image redefine
how we interpret Gatsby’s life and death?
4. Consider what you know about the
archetype of the tragic hero:
someone who is noble and/or has
high status, one whose story causes
fear and pity to arise amongst the
audience members, and one whose
downfall is caused by a fatal flaw
(hubris, i.e. excessive pride). To
what extent, if at all, can Jay
Gatsby be considered a tragic hero?
What, if anything, is tragic about
his story? What is the overall
commentary Fitzgerald is making
through his life and his death?
Moskovian: AP Language 9