Preface: Introducing the conceit that the letters were "found" and are "true", although Lewis takes care to point out that the devil is a liar.
1.With no introduction or exposition, we meet Screwtape and discover that he has been around for centuries, and perhaps indeed, his sense of time is very different from ours. This chapter makes clear the relationship of the two devils and the sense that Screwtape is retired, but perhaps is spying on or is responsible for his nephew's work. We also hear of the Enemy (God), and how the devil can accomplish much by simple distraction.
2.The introduction of Christianity as a powerful weapon of the Enemy, and how it may be turned to the devil's use. This chapter also introduces Screwtape's view of God's plan to create free "sons".
3.The relationship of the man and his mother, and the irritation and distance that can arise with long intimacy with someone.
4.A discourse on prayer and the methods to distort or misuse this powerful tool of communication with the Enemy.
5.The introduction of the War and the sudden awareness of death, plus the idea that demons "drink" the suffering and anguish of the human soul.
6.How to redirect good impulses inward and feelings of hatred and malice outward.
7.How it affects humans to be in ignorance of the devil, and whether the man should be encouraged to be an extreme Patriot or Pacifist.
8.The Law of Undulation (troughs and peaks in a human life), and the appalling truth of the Enemy's love for the "loathsome little replicas of Himself".
9.Exploiting the troughs and peaks with sensual temptations, with the confession that all Pleasures are the work of the Enemy. Convincing the man that the peak of religious conversion was just a "phase".
10.The importance of the man's social circle as influences and misleaders. The devilish connotation of the word Puritan.
11.The causes of human laughter divided into Joy, Fun, the Joke Proper, and Flippancy, of which Flippancy is most beloved of Screwtape. How vices may be passed off as funny. The comparison of Joy to Music, "that detestable art".
12.The repentance and renewed Grace of the man, and how he may be retrieved from the Enemy.
13.How the smallest sin can have a great impact on human character. "Murder is no better than cards if cards can do the trick."
14.A discussion of the meaning of humility, and the reemphasis of the Enemy's love for humankind.
15.How humans can live in the Past, Present, and the Future, and "Anyway, why should the creature be happy"?
16.Church shopping and the useful divisions between "high" and "low" churches. "A positive hotbed of charity and humility".
17.How one can be a glutton of delicacy, and the spurious relationship of physical exercise and chastity.
18.Sexual temptation and the transcendental relationship of a man and woman who are sexually connected. The nature of marriage and the family as desired by God and as desired by the devil.
19.After an apparent attempt to blackmail Screwtape, he retracts his earlier statements about the Enemy really loving humans, and the real motive being unknown. A brief discussion of the devil's original division from God.
20.A discussion of current ideals of feminine beauty and how they induce both men and women to desire something that doesn't really exist, which leads Screwtape to the idea of the "terrestrial and infernal Venus" that preoccupy most men.
21.The belief of humans that they own their time, and own their bodies.
22.The man falls in love, and Screwtape becomes so enraged that he inadvertently transforms into a large centipede. (reference to G. B. Shaw)
23.How to corrupt spirituality, including a discussion of the the concept of the "historical Jesus".
24.A discussion of Spiritual Pride, and a dismissal of the details of the European War, in which Screwtape is not the least bit interested.
25.A mention of mere Christianity, and an in depth exploration of the Enemy's desire that humans experience a blend of novelty and familiarity in their lives. How devils work with the tastes of the age to defeat and enslave humans.
26.The difference between Unselfishness and Charity.
27.How the Enemy answers the prayers of humans. (reference to Henry Ford as "the most ignorant mechanic")
28.How humans become more attached to the World with time.
29.A discussion of the emotions of Shame, Hate, and Fear, which occur so often in humans in wartime.
30.The increasing impatience of Screwtape at the incompetence of his nephew Wormwood. The notion of the "real world" and how that idea may be twisted every which way to influence the man to spiritual harm.
31.The death and redemption of the human and the fierce, hungry desire of Screwtape for Wormwood. Screwtape Proposes a Toast (this was added nearly twenty years after the original letters were written, in 1962) Screwtape describes the current trend toward more but less significant sinners. In this discussion he describes England at the turn of the century, in which old-fashioned exploitation of the lower classes was going out of fashion. However, the devil contrived both the Nazi and the Communist state. He goes on to describe how the simple word, democracy, can be used to sanction the efforts of any who feel inferior to pull others down to their own level. Further, that in trying to insist that all humans are equal, they are thus prevented from being in any way individuals. Finally, Screwtape offers them a toast to the College and its principal Slubgob, as they raise their glasses of vintage Pharisee.