1. Richard Shelton first appears as a rather naive young man who accepts appearances without understanding the more complex reality of the world in which he lives. How does he become more enlightened and mature?

2. Dick begins as a male chauvinist with no use for women. How does he come to respect, and then to love, Joanna Sedley?

3. To what extent does Joanna qualify as a liberated heroine, and to what extent is she the stereotypical heroine of romantic fiction whom the hero must rescue?

4. In books 1 and 2, Joanna Sedley plays a major role; in the remaining three books she appears only briefly, and Stevenson introduces another woman, Alicia Risingham, as a possible rival for Dick's love. Is it a mistake for him to remove Joanna after book 2?

5. In Shakespeare's plays, in popular mythology, and in such films as the two versions of The Tower of London (1939 and 1961), Richard III is a figure of monstrous evil. Stevenson's Richard of Gloucester will become Richard III, but in this novel he is a younger man, not yet steeped in crime, who befriends the hero and advances him. What evidence is there that Richard has the potential for evil and that Dick does well not to remain one of his followers?

6. In The Black Arrow, a story of civil war, loyalties and alliances shift. How does Dick discover that his supposed protector, Sir Daniel Brackley, has betrayed him? In changing sides, does Dick turn traitor or discover a new freedom? Are the outlaws subversive criminals, terrorists, or freedom fighters? Why do Richard and his new protector, Richard of Gloucester, become alienated? What does this alienation say about each of their characters? Is either the side of York or of Lancaster better than the other?

7. Are there any parallels between the political situations of the Wars of the Roses in The Black Arrow and the political situations of quarreling factions today?

8. Is the novel's archaic prose style and diction a help or hindrance to the narrative? Can it be justified in terms of realism, or is it an artifice?