Discussion Questions to Ponder

Hi everyone, here are a few questions (from the publisher) to ponder – just some food for thought.

1. How does Nate see himself, and how does this differ from the way his girlfriends see him? What is your view of Nate? Are you able to sympathize with his thoughts or actions? If you had to summarize what his main character flaw is, what would you say it is?

2. The book delves into the psyche of a man, yet it is written by a woman. What effect does this have on the overall conversation and tone of the narrative? How would it be different if a man had written the book?

3. How important a role does Brooklyn play as the novel’s locale? Could the story have been placed anywhere else?

4. Despite the fact that Nate initially found Hannah to be different from the other women he had dated, his attitude toward her eventually begins to change. Do you think there is a legitimate reason for this change? Or does it reflect a limitation of Nate’s? What do you think keeps the relationship going after the initial excitement has died down?

5. Nate has relationships with many different kinds of women, and yet he can’t seem to be content with any of them—Kristen the socially conscious do-gooder, Elisa the beautiful, and Hannah, who exhibits both cool and intelligence. Nat wonders, “Why [do] women say men [are] threatened by women who challenge them?” Do you believe that, in spite of his claim not to be, Nate may be threatened on some level? Is he truly finding himself incompatible with these women, or are his breakups results of his own insecurities? All of them or only certain ones?