1. After the Adam "debacle" in chapter one, Roo and Kim begin a notebook called The Boy Book in which they write down everything they know about boys. Have you ever started a book like this on your own or with your friends? Do you think it would be useful? What information would you include?
2. On page 41, Ruby spills her guts to Kim about Finn. Is this smart? Are there circumstances in which it’s better to keep your mouth shut? Has something like this ever happened to you–you tried to do the right thing and it backfired?
3. Ruby gives three examples of the way love works in the movies. In her example on page 64, the couples hate each other half the time but still get together in the end. In her example on page 65, the couple breaks up, but then the man realizes that he loves the woman and can’t exist without her, and they get back together and live happily ever after. And on page 198, the hopeless dorky guy who’s been there all along eventually gets the girl. Do you agree with Ruby that these happy endings don’t happen in real life? Pick one of the movies mentioned and discuss it. Does the romantic situation in the movie ring true? Can you think of other movies, books, or television shows that would fit on Ruby’s lists?
4. Ruby discovers that dating Jackson isn’t the way she thought dating was supposed to be. Have you ever discovered that your ideas about something were wrong? How was the reality different from what you had imagined?
5. In chapter six, Kim and Ruby invent the perfect boyfriend and name him Tommy Hazard. Do you have your own Tommy Hazard? Are there hazards in creating a "perfect" boyfriend?
6. After stealing Jackson, Kim tells Ruby, "When you find your Tommy Hazard you’ll understand. I honestly couldn’t help it." Doyou agree with Kim’s justification of her behavior? Does she dothe right thing?
7. Even though Noel has become Roo’s only ally, she turns on him on page 176 after he says, ". . . if those are your friends you’ve got no need for enemies." Why does this upset Ruby so much? Do you think Noel is right? Why is Ruby not yet ready to give up her old life, even though it has become the source of such pain?
8. When Kim calls Ruby a slut in class, Mr. Wallace gives a lecture on the negative effects of labels and points out that "there are no equivalent epithets for men whatsoever, and didn’t that say something about how women are viewed in our culture?" (page 177). What does it say? Can you give examples of the negative effects of labels, from real life or from movies, music, television shows, or books?
9. Ruby ends the book by saying, "I was out of the Tate universe, standing on the edge of the sea" (page 229). What does she mean by this? Is she really out of the Tate universe? Is this a satisfying ending? Do you believe that Ruby is in a better place now than when the book began? What do you think is next for her?