You have a wide array from which to choose. If your class is able to understand the history, I think that a good question to ask would be how the work reflects the time period. What is Fitzgerald saying about the 1920s, in general? What is Fitzgerald suggesting about conformity and being a part of the social elite? I think that this could spawn into a very interesting discussion about how he shows personal cruelty. I think that a very good discussion point in the novel is the different levels of cruelty that is evident. As readers, it is important to find examples of this cruelty to see if it is replicated in our own lives or if we have learned anything from it. Another question that should reveal some interesting discussion would be how Fitzgerald defines love. Is there any character in the novel that really "loves" another? If so, what does it mean to love? Is there a difference between "love" and the idea of "being in love?" I think that this might be interesting to assess in a class forum. Finally, I think there should be a discussion about the American Dream. What does it mean? How close does Fitzgerald link the American Dream to the American Nightmare? I think that this might be a very interesting point of discussion.