1. This is a novel about a brother and a sister. How would you describe their relationship? How do Robin and Ruby seem alike? How do they seem different from each other? Do their separate stories share any common themes?

2. The story is set in the summer of 1985. Which scenes in the story made this time period come alive for you? How do social issues or news events shape the lives of the characters in this book?

3. The entire novel takes place during the weekend when Jackson, Robin and Ruby’s deceased younger brother, would have turned 18. How does Jackson’s death influence the events of the story?

4. The book opens with the line, “Sometimes life throws you a job that you’re not yet ready to do.” What kinds of challenges is Robin forced to face, and how does he deal with them, over the course of the novel?

5. Robin and George have been friends for years, and have never had sex before. Why do you think it finally happened at this time? What emotions and tensions arise after their first night together?

6. Why does Robin decide to look for Ruby? Why does George agree to go with him?

7. We meet Ruby a couple years after she has stopped believing in God, though she still finds herself praying (“the leftover habit of prayer”). How do questions of belief and faith emerge throughout Ruby’s story? Does she come to terms with these questions?

8. Ruby makes a choice to leave Calvin for Chris. Do you think she made a good choice? As Ruby spends more time with Chris, and gets to know him better, did you feelings for him change?

9. What kind of person is Calvin? Did you see Calvin differently by the end of the book than at the beginning?

10. Ruby’s sexual history is revealed slowly to the reader, and she doesn’t always tell the truth to other characters. Why do you think she has so much conflict and secrecy around her sexuality?

11. When Ruby is with Alice and their crowd, she “feels like a soft, small toy batted around by enormous paws in a room filled with cats.” Later, she asks them, “Why are you all so mean to me?” What do you think is the answer to that question?

12. When Robin and Ruby return to Greenlawn, they are confronted by their parents, Dorothy and Clark. How would you describe Robin’s relationships to his parents, compared to Ruby’s? What about Clark and Dorothy’s relationship to each other?

13. Back in his childhood bedroom, Robin reads from an old diary and comes to the conclusion that he needs more “courage, for what comes next.” What do you imagine comes next for Robin? What will he need courage for? What might the future hold for Robin and George?

14. After her final phone call with Chris, Ruby thinks, “And in this moment her entire life realigns. What matters and what doesn’t.” What do you think matters to Ruby at the end of the book? What kind of future will she have, if any, with Chris?

15. Robin and Ruby is a sequel to The World of Normal Boys. If you’ve read that book, were you surprised by what happened to Robin, Ruby, Dorothy and Clark in the years that have passed? Did their lives turn out like you imagined?