1.  The three main characters in this novel – a man, a woman, and a young boy – are all running from something. They find common ground with each other in a big city (Minneapolis) night. Could they have found each other in a different location or setting? Somewhere other than Big City, USA?

2.  Early in the book, on page 11, "Dark Dog" thinks "[t]he couldn’t-be child would never give the used-to-be man any peace until he emerged and followed and scared off the threat, one beast to another." Here Jesse Brown Wolf is referring to Tommy T. who coaxes him out of the cave to stop a shooting that involved Tommy T’s brother. How does this passage foreshadow a major plot in the story?

3.  Angela is roughed up by some gang members. Tommy T. finds her and goes to his hero for help. Jesse takes Angela into his cave to help her recover and she thought, "Like Alice she had fallen down a deep, dark hole. Are there any other fairytales this book brings to mind?

4.  Throughout the book, it seems there are many comparisons between many ways of life. The dark cave of Jesse Brown Wolf is referenced by Tommy T. when he waits outside the café where Angela is working: "He liked the way the city felt at night when a guy knew he had a friend close by. Sort of insulated from the rest of the world, like one big house with lots of lights left on. But the friend was important. Without a friend, the house felt more like a cold pit crawling with bugs." Then there are the comparisons of Angela and Darlene, Gayla and Darlene’s daughter, Stoner and his buddies with Chopper and his gang, the poor living in tiny, run-down apartments, and the rich in mansions overlooking the river, and the Many Nations School with other schools of supposedly only one nation. Why all these comparisons of seeming opposites?

5.  Why is it that Jesse Brown Wolf can "fix" everything from bad plumbing to bad situations but remains unable to "fix" himself?

6.  Both Tommy T. and Jesse Brown Wolf live in a world better suited for the night where they hide parts of themselves. Both of them keep parts of themselves in parts of others’ lives; Jesse keeps his tools in Darlene’s closet and Tommy T. keeps his comics in Angela’s closet. What other parallels between the child and the man are revealed?

7.  Examine how Jesse can "shapeshift" into Dark Dog for Tommy T., phantom lover for Angela, and even into Coyote for himself. Is this "shapshifting" theme explaining something about Jesse Brown Wolf, about humanity?

8.  When Jesse Brown Wolf gets shot on the playground, Angela goes to his cave and tends his wounds. Why does the author allow this role exchange between these two characters?

9.  Often religion plays huge roles in fiction. What religious themes are found in this novel if any?

10. In the epilogue, we see Tommy T. trying to adjust to his new life off of the streets, and he misses his freedom, dangers aside. In ending of Twain’s Huckleberry Finn, Huck tries to adjust to his new live off of the Mississippi River, and into a family home (civilization). Will Tommy T. chuck it all and head back to the streets and his brother the way Huck chucks it all and runs through the fields towards freedom, and the river – the same river on which Tommy T. roams the bluffs?