This Side of Paradise includes a number of poems by Amory and other characters, such as Eleanor. Reread these poems and discuss their style and themes. What role do they play in the novel, and what is their relationship to Amory’s intellectual development? What do you think of the poems? Why do you think Fitzgerald includes them? How do they go about expressing themes such as traditionalism, radicalism, paganism, or other themes that you can see in them? Is their style similar to that of the novel itself? Are they modernist poems? Explain why or why not.

Fitzgerald’s personal life has long fascinated critics. Read Arthur Mizener’s biographical work The Far Side of Paradise (1951) or another biography of Fitzgerald paying particular attention to his life before 1920, and discuss how what you have read affects your understanding of This Side of Paradise. How are the personalities and experiences in Fitzgerald’s life directly or indirectly included in his first novel? Discuss why you think Fitzgerald used certain events from his life in the novel, and how you think critics should treat knowledge of an author’s life when they are discussing his or her writings.

Amory is characterized as a self-absorbed egotist in the novel. Do you think this is an undesirable trait? What are its positive aspects? By the end of the novel, does Amory think it is undesirable? Does Fitzgerald? Do you think Amory’s personality will change? Why do you think Fitzgerald wrote a book about such a character? How is egotism important to the novel’s place in literary history?

Two of the most important scenes in This Side of Paradise are written in the format of a play. Find a cast of characters and act out these scenes. Afterwards, discuss how this experience adds to your understanding of the novel, as well as how these scenes affect the rest of the book. Why you think Fitzgerald chose to use the dramatic form? Is it a success, and does it work well in the book? Why or why not?