1. Are Hannah’s insecurities similar to those of other young women? Is she an extreme case, or are most young women beset by insecurities?
2. What do the men Hannah dates think about her? How might their perception of her be different from her perception of herself?
3. Do you feel more sympathetic to or frustrated by Hannah? Do you consider it important for fictional characters to be “likable”? Why or why not?
4. How do you think the rocky marriage of Hannah’s parents–and her father’s harsh temper–shaped her attitudes toward men? Why does her sister, Allison, seem to have less trouble ﬁnding domestic tranquility?
5. Most of this book is told in the third person, yet it ends in the ﬁrst person, with a long letter that Hannah writes. Why do you think the author chose to end the book this way?
6. Do you think this book has a happy ending?
7. Do you think the title of this book is appropriate or misleading?
8. If you are married or in a relationship, is it with the person of your dreams? How has your definition of this phrase changed over time? If you are single, do you believe in the idea of soul mates?