1. Much of the appeal The Screwtape Letters derives from Lewis's startlingly original reversal: telling a story about Christian faith not from a Christian point-of-view but from the perspective of a devil trying to secure the damnation of one's man's soul. Why is this strategy so effective? What does it allow Lewis to accomplish that would have been impossible in a more straightforward approach?

2. In the first of Screwtape's letters, he instructs Wormwood not to attempt to win the patient's soul through argument, but rather by fixing his attention on "the stream of immediate sense experiences" (p. 2). Why is immersion in the particulars of "real life" fertile ground for temptation? Why is argument a risky strategy for devils to employ? Where else do you find this opposition between the particular and the universal-between materialism and spiritual faith-in The Screwtape Letters?

3. While Screwtape allows that war is "entertaining" and provides "legitimate and pleasing refreshment for our myriads of toiling workers," (p. 18) he fears that "if we are not careful, we shall see thousands turning in this tribulation to the Enemy, while tens of thousands who do not go so far will nevertheless have their attentions diverted from themselves to causes which they believe to be higher than the self" (p. 19). Why would war have this effect? How does war alter human consciousness in a way unfavorable to temptation? How would you relate Lewis's own experience in WWI, which apparently confirmed his youthful atheism, to his position in The Screwtape Letters?

4. In describing the differences in how God and the Devil view men, Screwtape says: "We want cattle who can finally become food; He wants servants who can finally become sons" (p. 30). What is it about God's relationship to man that Screwtape finds so unfathomable?

5. Why is Screwtape so pleased when the patient becomes friends with a group of people who are "rich, smart, superficially intellectual, and brightly skeptical about everything in the world"? (p. 37). What influence does Screwtape hope they will have on him? Why should their "flippancy" build up an "armor-plating" against God? In what ways does Lewis merge theology and social satire in this and other passages throughout The Screwtape Letters?

6. Screwtape assures Wormwood that although some ancient writers, such as Boethius, might reveal powerful secrets to humans, they have been rendered powerless by "the Historical Point of View," which regards such writers not as sources of truth but merely as objects of scholarly speculation. "To regard the ancient writer as a possible source of knowledge-to anticipate that what he said could possibly modify your thoughts or your behavior-this would be regarded as unutterably simple-minded" (p. 108). Why would Screwtape delight in this situation? How would he turn it to his advantage? How does this view of reading parallel post-modern approaches to literature? Where else does Screwtape encourage Wormwood to persuade humans that truth is irrelevant?

7. Lewis exhibits throughout his writings an uncanny sense of human nature and a style capable of brilliant aphorism: "Men are not angered by mere misfortune but by misfortune conceived as injury" (p. 81); ; "Gratitude looks toward the past and love to the present; fear, avarice, lust, and ambition look ahead" (p. 58), to cite just two examples. Where else in The Screwtape Letters do you find universal statements about human nature? Do these statements accurately reflect not just a Christian ethos but the workings of human psychology more generally?

8. The sub-plot of The Screwtape Letters turns on Screwtape's relationship with his nephew Wormwood, the apprentice tempter and demonic understudy in charge of carrying out Screwtape's instructions. How do Screwtape and Wormwood regard each other? How does their relationship change over the course of the book? In what ways does their relationship offer an inverted reflection of God's relationship to man? What is Lewis suggesting by having the story end with Screwtape preparing to devour a member of his own family?

9. In discussing time, change, and pleasure, Screwtape asserts that "just as we pick out and exaggerate the pleasure of eating to produce gluttony, so we pick out this natural pleasantness of change and twist it into a demand for absolute novelty" (p. 98). Why is the demand for novelty necessarily destructive? What natural balance does such a demand disrupt? In what areas do you find this insistence on change, or overvaluation of the new, operating today?

10. Love is an important theme in The Screwtape Letters. Describing the human idea of love and marriage, Screwtape tells Wormwood: "They regard the intention of loyalty to a partnership for mutual help, for the preservation of chastity, and for the transmission of life as something lower than a storm of emotion" (p. 72). Screwtape is also confounded by God's love for man, which he grants as real but irrational. What is Lewis saying, in the book as a whole, about human and divine love?

11. Over the course of The Screwtape Letters, the state of the patient's soul fluctuates as he experiences a conversion, doubt, dangerous friendships, war, love, and finally, in death, oneness with God. What major strategies does Screwtape use to tempt the patient into the Devil's camp? Why do these temptations fail? In what ways can the patient be seen as an everyman?

12. In spite the patient's triumph over temptation, his glorious entrance to Heaven-"the degradation of it!-that this thing of earth and slime could stand upright and converse with spirits" (p.122)-Screwtape does not lose faith in his own cause. Why do you think Lewis chose to end the book in this ambiguous light? Why is Screwtape sustained by "the conviction that our Realism, our rejection (in the face of all temptations) of all silly nonsense and claptrap, must win in the end"? (p. 124). What warning is implied in the book's ending? In what ways does The Screwtape Letters speak to contemporary moral and spiritual issues both within and outside of the Christian Church?