14-Week Study & Discussion Guide

The Screwtape Letters

by C.S. Lewis·99 discussion questions

Last updated August 16, 2026

Week 1 — FreeRead Lewis's Preface and the opening framing of The Screwtape Letters. Key passages: 1 Peter 5:8; 2 Corinthians 2:11

Discussion question your group will work through:

1.In his Preface, Lewis warns against two equal and opposite errors regarding the Devil: treating him as a pantomime villain on one hand, or as a brooding romantic figure on the other. Which of these errors do you find more tempting in your own thinking, and why?

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About This Study Guide

At a glance: this is a 14-week study and discussion guide for The Screwtape Letters by C.S. Lewis, with 99 questions organized by reading assignment. Week 1 is free to read, with no card required.

C. S. Lewis's The Screwtape Letters is one of the most original and penetrating works of Christian apologetics ever written. Cast as a series of letters from the senior demon Screwtape to his bumbling nephew Wormwood, the book turns the usual perspective on temptation inside out: we see humanity not through the eyes of a saint or a pastor, but through the eyes of hell. The result is both darkly comic and deeply convicting. Lewis's central argument is that the Enemy (God, from hell's perspective) is relentlessly pursuing the love and free will of every human soul, while the demons work not through dramatic supernatural horror but through the quiet, corrosive power of distraction, self-deception, and spiritual complacency. Written against the backdrop of World War II, the letters expose how ordinary life — marriage, friendship, politics, pleasure, and even church attendance — becomes the battlefield for the soul.

This study guide is designed for small groups or individuals who want to read The Screwtape Letters slowly and honestly, letting Lewis's inverted satire act as a mirror. Each week, read the assigned letters, then sit with the discussion questions — ideally journaling your answers before meeting with your group. Because Lewis numbers his letters rather than titling chapters, the guide groups letters thematically as they naturally fall, following the arc of "the Patient's" spiritual life from his conversion to his death. You do not need a theological degree to benefit from this guide; you need only a willingness to recognize yourself in the Patient, and occasionally in Wormwood.

By the end of the book and this guide, you should have a sharper eye for the subtle strategies hell uses against ordinary Christians, a deeper appreciation for the radical goodness of God that Lewis calls "the Enemy," and a renewed desire to pursue what Screwtape, in a moment of frustrated honesty, calls "real joy" — the kind Hell can neither manufacture nor destroy. Come to these pages ready to laugh, to wince, and to pray.

Preface & Introduction — Letters from Below

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Read Lewis's Preface and the opening framing of The Screwtape Letters. Key passages: 1 Peter 5:8; 2 Corinthians 2:11

Before diving into the letters themselves, Lewis asks us to consider how we think about evil — and whether our usual mental habits help or hurt us. Take a few minutes to consider what you already believe about the Devil and temptation.

2.Lewis chose the form of letters from a demon to tell his story — a deliberately 'inverted' perspective where God is called 'the Enemy' and the human soul is called 'the Patient.' What does this reversal accomplish that a straightforward sermon or essay could not?

3.Lewis admits in the Preface that writing the book was 'not fun' and felt spiritually draining — he had to inhabit a demonic mindset for an extended period. What does that say about the nature of serious engagement with the topic of evil? Have you ever found that studying sin or temptation closely was itself spiritually costly?

a.How might this be a caution for how we engage with dark or disturbing spiritual content — in books, films, or conversation?

b.How is Lewis's discomfort actually a mark of his own spiritual health?

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14-Week Schedule

Letters 1–5 — The New Convert

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Read Letters 1–5 of The Screwtape Letters. Key passages: Romans 10:17; Hebrews 11:1; James 1:5–8

1.In Letter 1, Screwtape rebukes Wormwood for allowing the Patient to become a Christian and immediately offers a strategy: keep him thinking about his faith rather than living it, and use 'the stream of immediate sense impressions' to drown out any genuine spiritual reflection. Where do you see this strategy at work in contemporary Christian culture?

+ 6 more questions in the full guide

Letters 6–10 — The Patient's Family and Inner Life

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Read Letters 6–10 of The Screwtape Letters. Key passages: Ephesians 4:26–27; Matthew 5:21–24; Colossians 3:12–14

1.In Letter 6, Screwtape explains the strategic value of the 'domestic setting' — the home — as a place where irritations are constant, defenses are down, and the Patient is most likely to act contrary to his best self. Do you agree that home is a more spiritually revealing arena than, say, church or work? Why or why not?

+ 6 more questions in the full guide

Letters 11–16 — Pleasures, Pride, and the Fashionable Crowd

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Read Letters 11–16 of The Screwtape Letters. Key passages: 1 John 2:15–17; Proverbs 16:18; Romans 12:2

1.In Letter 11, Screwtape distinguishes between different kinds of laughter and humor. He identifies 'flippancy' as hell's favorite — a humor that treats everything serious as comic and thus prevents any real engagement with truth or goodness. How would you distinguish flippancy from the genuine, life-affirming humor that Lewis elsewhere celebrated? Can you give an example of each?

+ 6 more questions in the full guide

Letters 17–22 — Love, Sex, and Marriage

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Read Letters 17–22 of The Screwtape Letters. Key passages: Genesis 2:24; 1 Corinthians 13:4–7; Ephesians 5:25–33

1.In Letter 17, Screwtape discusses the demonic strategy around gluttony — and surprises us by focusing not on gross excess but on what he calls 'the gluttony of Delicacy': the fussy, demanding, never-satisfied pickiness that is all about self rather than nourishment. Have you ever recognized gluttony in this more subtle form — in food, entertainment, comfort, or attention?

+ 6 more questions in the full guide

Letters 23–26 — The Church, Spiritual Fashions, and 'Unselfishness'

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Read Letters 23–26 of The Screwtape Letters. Key passages: 1 Corinthians 1:10–13; Matthew 23:23–28; Philippians 2:3–4

1.In Letter 23, Screwtape celebrates the 'Church-hopper' — the Christian who has developed a critical eye for finding fault with every congregation and thus remains permanently detached from real, costly community. Does this portrait resonate with anything you've observed? What is the spiritual cost of approaching church as a consumer?

+ 6 more questions in the full guide

Letters 27–31 — Courage, Death, and the Patient's Homecoming

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Read Letters 27–31 of The Screwtape Letters. Key passages: Romans 8:35–39; 1 Corinthians 15:54–57; Revelation 21:4

1.In Letter 27, Screwtape addresses the strategy of using 'historical perspective' and intellectual cowardice to keep Christians from firm commitment — nudging them to always see 'the other side' until they have no side at all. Lewis called this the sin of 'being open-minded as a permanent condition rather than a path to truth.' Where do you see this kind of paralyzed open-mindedness in contemporary culture or in yourself?

+ 6 more questions in the full guide

'Screwtape Proposes a Toast' — Bonus Essay

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Read 'Screwtape Proposes a Toast' (included in most modern editions of The Screwtape Letters). Key passages: Luke 18:9–14; Matthew 20:1–16; Romans 12:6–8

1.Screwtape's 'Toast' is a speech at a demonic graduation banquet, and he opens by lamenting the poor quality of modern souls being served as food — 'the gentle Pharisee, the scrupulous Judas.' What does this dark humor suggest about Lewis's view of what makes a soul 'flavorful' to hell — i.e., what qualities make someone more or less easily corrupted?

+ 6 more questions in the full guide

Lewis's Vision of Evil — A Theological Pause

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Re-read selected letters of your choice from The Screwtape Letters, focusing on Screwtape's descriptions of God and of hell's own nature. Key passages: Isaiah 14:12–15; John 10:10; 1 John 4:7–8

1.Throughout the letters, God is called 'the Enemy' — but Screwtape's descriptions of him, filtered through demonic frustration, are often unexpectedly beautiful. What portrait of God emerges from what Screwtape grudgingly admits about him? List two or three attributes that Screwtape acknowledges even while resenting them.

+ 6 more questions in the full guide

Lewis as Apologist — The Craft and Purpose of Satire

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Read or re-read the Preface of The Screwtape Letters alongside Lewis's essay 'On Stories' (if available). Key passage: Proverbs 26:5; Matthew 13:10–13

1.Lewis said that The Screwtape Letters was the most successful and the most hated of all his books — readers loved it but he found it oppressive to write. Why do you think inhabiting an evil character's perspective for an extended time might be spiritually draining? What does that tell us about Lewis's own spiritual seriousness?

+ 6 more questions in the full guide

Applying Screwtape — Recognizing Temptation in Daily Life

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Re-read two or three letters that have been most personally convicting. Key passages: 1 Corinthians 10:13; James 4:7; Ephesians 6:10–18

1.Look back at the list you made in Week 1 of areas where you felt most spiritually vulnerable. Which of Screwtape's named strategies — distraction, flippancy, domestic irritation, spiritual troughs, pride disguised as virtue, anxiety about the future, etc. — most accurately names what you face? Be as specific as you can.

+ 6 more questions in the full guide

Lewis and His World — Context and Biography

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No new reading from the text this week; revisit any portions you found most striking. Recommended: read a short biographical essay on C. S. Lewis if available. Key passage: 2 Timothy 3:16–17

1.C. S. Lewis converted to Christianity as an adult after many years as a committed atheist and materialist. How do you think this journey shaped the particular targets he chose for Screwtape's attacks? What temptations might a former atheist intellectual understand especially well?

+ 6 more questions in the full guide

Screwtape and Scripture — A Comparative Study

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Select 4–5 letters from The Screwtape Letters alongside corresponding Scripture passages. Suggested pairings included below. Key passages: James 1:13–15; 1 Peter 5:6–11; Galatians 5:16–26

1.James 1:13–15 describes the anatomy of temptation: desire, enticement, sin, death. How does Screwtape's model of temptation — working through distraction, ambient atmosphere, and the corruption of good desires — map onto James's account? Where do they align and where does Lewis go further?

+ 6 more questions in the full guide

Review & Reflection — What Has Hell Taught Us About Heaven?

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No new reading. Review your notes, journal entries, and underlined passages from The Screwtape Letters over the whole course of this study

1.Which letter or theme from The Screwtape Letters had the most impact on you personally? What was it about that particular passage that got through your defenses in a way other things hadn't?

+ 7 more questions in the full guide

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About the The Screwtape Letters guide

How many weeks is the The Screwtape Letters study guide?

This study guide covers The Screwtape Letters in 14 weeks, with week-by-week discussion questions, reading references, and closing prayers for each session.

How many discussion questions are included?

The complete guide includes 99 discussion questions across 14 weeks — an average of 7 questions per week, designed for group conversation.

Can I use this guide for a book club?

Yes — the questions are written for group discussion and work well for small groups, book clubs, church studies, and couples reading together.

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