By Rebecca Dana
BerkleyJanuary 2014

Trade Paperback304 pages, $15.00, ISBN: 9780425264935
Subject: Social Issues / Relationships / Religion

  1. Rebecca has always dreamed of moving to New York and creating a life like Carrie Bradshaw’s Sex and the City. When she arrives, she immediately feels like she is home. Why is New York so important to her? What is her perception of the city? Is this perception false? Does it change over time?
  2. After first meeting Cosmo and touring the apartment in Crown Heights, Rebecca leaves feeling relieved she’ll never see him again. What changes her mind and makes her want to move in? Do you think she sees this as a temporary escape or as a chance to begin a journey of self-discovery?
  3. Although they come from completely different worlds, Cosmo and Rebecca become unlikely friends who are each at surprisingly similar crossroads in their lives. Compare and contrast their individual crises—Rebecca as newly single, and Cosmo questioning his faith for the first time. How do they each deal with being thrust outside their comfort zone? Do they sympathize with each other? Why is their friendship so important for each of them during this time?
  4. Cosmo’s expressions and behavior—such as eating bacon raw—are comedic, although he isn’t trying to be funny. Why is he a great character for this book? Would you be his roommate?
  5. There is a sharp contrast between the secular world Rebecca lives in Manhattan—parties, celebrities, fashion, drugs—and her new ultra-Orthodox Brooklyn neighborhood. How is she an outsider in both? In which ways does she belong?
  6. Discuss the women Rebecca meets in the Lubavitch community. How are they unlike what she expects? Do you believe they are truly happy? Or are they oppressed, as so many in the secular world believe?
  7. After her week at the Yeshivacation, Rebecca realizes she is searching for a “community of meaning.” What does this come to mean to her? Does she eventually find it? How?
  8. All through her journey, the author is insistent that “We are not in dialogue with the Universe.” She believes the Universe doesn't send signs. Do you think this is true? Was the Universe sending her signs? Do you believe in signs, or have examples of when you felt the Universe sent you a sign?
  9. Has your perception of ultra-Orthodox Jews changed after reading this book? What did you learn about their culture that was unexpected?
  10. Rebecca thinks she has achieved her perfect life in the beginning of the book but after her relationship ends, she realizes she still has a lot of work to do. How can a derailment from the life you thought you wanted end up being a good thing? Discuss a time when something threw you off course from the future you thought you would have, and how it turned out.
  11. Near the end of her stay in Crown Heights, Rebecca realizes: “You have to stop living as the person you want to be and start living as the person you are.” What are the differences between the person she wants to be and the person she is? How does she eventually make peace with her true self?
  12. Although surrounded by religion, is this really a spiritual journey for Rebecca? Is her faith or relationship with God altered after living with Cosmo and the Lubavitchers?
  13. After returning to Manhattan, has Rebecca changed? What is and isn’t different about her? What are the most important things she’s learned? How does Cosmo’s transformation compare?