Bring on the tough stuff - there’s not just one right answer.
In the very last line of Chapter Three, Nick Carraway claims: "I am one of the few honest people that I have ever known." By the end of the book, Jordan Baker decides that this statement itself a lie. Is Nick Carraway honest? Dishonest? How would we know? If one muppet always tells the truth, and one muppet always lies, how do you know which way to go?
Is Nick Carraway necessary? If we got the story through a third person omniscient narrator, what would we lose? Gain?
According to the novel, what is it about the past that draws us both forward and leaves us stuck where we are? How can we be set free of the past? Can the novel Gatsby itself help us get free, or does it just leave us stuck in the past?
There's no mention of religion until the very end, when Myrtle Wilson's husband claims that he told his wife that she couldn't fool God. Why is this the first mention of God? How does this surprise mention of religion function within the rest of the story?
Could this story have taken place in other parts of the United States, like Chicago or Peoria, or were Long Island and New York City the necessary setting?
What might be the "something" that Nick is reminded of, yet cannot recall, at the end of Chapter Six? And isn't that moment totally confusing?
What is the effect of us getting the information out of order? We don't know the truth about Gatsby until Chapter 6, and we don't know the rest of the truth until Chapter 8. We get even more information when Jay's father shows up; what's the deal?
Is Gatsby great? In what way? How might he not be great? Does his greatness evolve over the course of the novel? What is the difference, in this text, between perceived greatness and actual greatness?
How does the character of Nick (inside the story, not the voice telling it) change over the course of the novel? What about the narrative voice? Although the entire story is told in retrospect, does the act of telling it create changes in his narrative style? Could it be that both character-Nick and narrator-Nick are changed?
Who really was driving when Myrtle was struck and killed? Can Nick be sure? Can we? If Nick insists that a person shouldn't criticize others, then why does it matter who killed her?
Take a look at Nick's opening lines. If we take this advice when we read The Great Gatsby, do our views of the novel change? Does refraining from criticism promote compassion, or amorality? Is criticism actually necessary?