Fleishman Is in Trouble

Like the narrator of the novel, Taffy Brodesser-Akner has written for men’s publications such as GQ, and ESPN the Magazine. How do you think this experience might have helped her write the novel? Is it fair to assume the author is like the narrator in any way? Why or why not?

The narrator portrays Toby in both a critical and a sympathetic light. In your opinion, is Toby more deserving of sympathy or blame?

Through Toby’s eyes, Rachel is made to seem like an uncaring parent. Is this a fair or accurate assumption? Give a reason for your answer.

Fleishman Is in Trouble is told in a unique narrative style, which includes both close third-person and first-person narration. How is this narrative strategy effective? How is it distracting? Did you like it? Why or why not?

In what ways do Toby and Rachel live up to gender expectations, and in what ways do they defy them?

In the end, is Seth a good, well-intentioned person, or is he problematic in some ways, e.g., his penchant for womanizing?

The narrator suggests that, except for the friends you make in college, “Life is a process in which you collect people and prune them when they stop working for you” (283). In what ways does the novel illustrate this to be true, and in what ways does it show it to be false?

Toby both enjoys the privileges of Rachel’s wealth and despises them. In the end, which attitude does the text seem to suggest is stronger in him? What do you think Toby’s professional future holds?