The Screwtape Letters Reading Guide

As October comes to an end I hope that you were able to enjoy this month’s book club selection, The Screwtape Letters by C.S. Lewis. I loved it. I couldn’t put it down. I don’t think many people truly give the enemy the credit that he deserves. I also don’t believe that people realize just how evil he is. I’ve always looked at him as the bad guy, but that didn’t really mean much.

This book opened up my mind and I realize just how manipulative the enemy is and how he blends in so well that often times we don’t even realize what he’s up to.

What did you think? Here is a study guide that may help trigger some thoughts. I’d love to hear what you have to say!

Study Guide: Courtesy of

How to use this study guide

As you read through the book, keep the following 3 questions in mind.

POWER OF LANGUAGE: How important are the words we use in our day-to-day lives? What can words do to our faith? Eminem said people should not be offended by his songs because “They’re just words.” What would Lewis (or Screwtape) say about that? What is Lewis’ view on how language works?

RELATIONSHIPS AND VIEWS OF OTHERS: What role do other people play in a person’s faith (both positive and negative)? There is frequent discussion about making assessments, or judgements, of others. How would Lewis view modern television advertisements in light of what they say about people, and what they say about what makes people happy?

POWER OF AMBIGUITY: How does ambiguity of words, beliefs, and feelings impact a person’s faith? How are these ambiguities increase by Screwtape? How might the church be contributing to ambiguity? What can we do to bring clarity to these ambiguities? What can the church do to encourage clarity, both in what they teach and what they do?

Letter 1

Screwtape reflects that people’s thought and behavior were at one time related in what way:
Screwtape encourages labels like ‘practical,’ ‘outworn,’ ‘strong,’ or ‘stark.’ How are these terms different than ‘true’ or ‘false.’
How does “argument” move “the struggle on to the Enemy’s own ground?”
What is “the pressure of the ordinary? How does it keep us from God?
What is the “abominable advantage” God has over Satan? Read Hebrews 2:14-18.
Why do you think Screwtape encourages propaganda over argument?

Letter 2
What is “the anticlimax” Lewis refers to?
What does Screwtape suggest happens to a Christian when they become less dependent on Emotions?
What does Screwtape mean by “parrot talk”? Matt 6:7
In what ways can church be an ally to Satan?

Letter 3
How is focusing your prayers for others on “spiritual” topics like the state of a person’s soul potentially inhibiting to prayer?
Screwtape says the patient thinks “his conversion is something inside him.” Screwtape suggests that this is not fully correct. What is conversion if it is not something inside a person? See Matt 7:21, 1 John 5:2-3.
What is the “double standard” Screwtape discusses?

Letter 4
What does Screwtape mean by the prayer mood ?
Screwtape states that humans “are animals and whatever their bodies do effects their souls.” What does he mean by that? Is it true? What other situations could our physical behavior effect our soul?
What importance does Screwtape make of the phrase ‘Not what I think thou art but what thou knowest thyself to be?” Exodus 3:14, 2 Samuel 22:26-28; 1 Cor. 13:11-12.

Letter 5
How does Screwtape propose using the past and present against us?
What does Screwtape think about war? Which is better for destroying someone’s relationship with God, according to Screwtape: going to war or going to a nursing home? Why?

Letter 6
What does suspense and anxiety do to keep people from God? Mark 4:18-19.
What does Screwtape mean by diverting the patient’s mind “from the thing feared to fear itself”?
Why might hatred of mother be more damaging to one’s soul than hatred of Osama bin Laden, according to Screwtape?
Screwtape says that God “wants people to be concerned with what they do, our business is to keep them thinking about what will happen to them.” How is being focused on what will happen to us destructive? See Matthew 7:24- 27, Eph 2:10, James 3:13.

Letter 7
Why would believing in demons keep a person from being “a materialist or a skeptic”?
How does the media inhibit our belief in demons and spirits?

Letter 8
What does undulation mean?
What, according to screwtape, is the purpose demons have in attacking humans? Read Matt26:26-29 and John 6:27-58 – How does this contrast with the intentions of demons?
Why are being ‘irresistible’ and ‘Indisputible’ two weapons God does not use to get humans?
Which is a more powerful display of Faith in a God, according to Screwtape:
A. A person who is on fire for God and does God’s will.
B. A person who feels abandoned by God, but does God’s will.

Letter 9
Why would Screwtape want to encourage words like “phase” regarding a person’s conversion experience?
According to Screwtape, are there any pleasures that are evil (bad)? Based on your answer, how can pleasure be destructive?
Why would Screwtape want to keep the patient away from experienced Christians during his dry spells?
Compare the Last paragraph of this Letter with the first paragraph of Letter one. What do both of these paragraphs say about language?

Letter 10
What does Screwtape mean by saying “All mortals tend to turn into the thing they are pretending to be”? Explain how this might happen. Give examples that you have seen if you can.
Given your answer to the previous question, what are the risks of associating with others?
If it is true that humans become who they are pretending to be, how can that truth improve our faith? I Cor. 4:16; Heb 6:1:12, 13:7; 3 John v.11.
Tell me about the two parallel lives Screwtape speaks of regarding the patient’s friends.

Letter 11
Why do you think flippancy “deadens, instead of sharpens, the intellect,” and keeps people from God?
Screwtape confesses that he does not know the real cause of Joy. What is the real cause of joy. See John 15:5-12, 16:19-24.
How can humor be used to excuse us from shame?

Letter 12
Why is having a vague, uneasy feeling that we are not doing well worse for us than recognizing clearly that we are being sinful?
What types of things, do you think, might increase vagueness?
Why does the “vague” feeling keep us from God, and the blatant, clear sin should not?
What is the “safest road to hell” according to Screwtape? Contrast with Matt 7:13,14.

Letter 13
What does Screwtape say about Pain and Pleasure? How are they related?
How does giving up innocent pleasures that you like for things that everybody else likes weaken one’s will?
What does Screwtape mean by “The more often he feels without acting, the less he will be able to act, and, in the long run, the less he will be able to feel?”

Letter 14
What is a way to ruin genuine humility?
Describe the type of Humility that would be what God wants for us:
Describe destructive ideas of what humility is:
Read Matt 23:2-12, then Mark 12:28-34. What is the vision of humility Jesus casts?

Letter 15
How is Strong Hope or Strong Fear about future events potentially damaging? Read Ecclesiastes 11:1-6.

Letter 16
Screwtape talks about sending the client “all over to churches.” In what ways do you think that is destructive to a person? What does it say about a person who searches until they find the church that “fits” them? What does it say about their view of church? Read II Tim. 4:3-5
Describe the two Vicars (preachers) Screwtape illustrates.

Letter 17
How is gluttony of delicacy different than gluttony of excess?
How does the woman’s gluttony affect her relationships with others?
How is the man’s gluttony related to vanity?

Letter 18
Screwtape says that marriage has been built up as an escape. An escape from what?
Screwtape says that “for us, [absorption] means the sucking of will and freedom out of a weaker self into a stronger.” How does this relate to #27.
How is “one flesh” different than a “happily married couple”?

Letter 19
What does Screwtape mean when he says that being in love, health or sickness, age or youth, war or peace are mainly just “Raw material?” How is this point important to our lives when these things occur?

Letter 20
How does Screwtape suggest in this Letter that sexuality can lead to destructive marriages?
Screwtape talks about the “sexual taste” of the age. What is the “sexual taste” of our age?
How does the media affect love relationships?
Are there male versions of the “venus type”? How would you describe it?
Compare Proverbs 7:21-27, 9:13-18 with 31:10-31. What do these verses say about female responsibility? What do they say about what a male should seek in a female?
Does 31:10-31 speak negatively about women?
If Proverbs was written by a woman, what would the description of the “man to avoid” be like? What would the description of the “man to seek” be like? See if you can support these with other verses.

Letter 21
What does Screwtape mean when he talks about people “making claims?”
He uses “time” and “bodies” as examples, what else do we “make claims” on? Read I Corinthians 6:19-20.
According to Screwtape, what is the “joke” on humans about their sense of ownership on things? Read James 4:13-17, Psalm 24:1, 100:3, and Romans 14:7-9.

Letter 22
Screwtape discusses a family that “reeks” of holiness where each individual in the group grow (“make capital”) off of each other. Do you have certain friends or family members that you feel “more holy,” or “more Godly” around? If so, describe what it is like being around them and discuss why you think you get this sense when you are around them (the more specifics the better).
Screwtape says “There are things for humans to do all day long without His minding in the least.” What pleasures does he mention?
How are these pleasures different than pleasures presented in the media?

Letter 23
Screwtape concludes the letter by saying “That’s the game,” referring to coaxing humans to believe Christianity “for some reason” other than the logical, rational truth of Chrisitanity. What are some of those other reasons people might profess to be Christians today.

Letter 24
Why is it spiritually dangerous to “be amused” at non-Christians?

Letter 25
What is the danger of striving to be different? Or, for having a passion to avoid “the Same Old Thing?”
Have you known people who strive to be different? Are they really successful? If they do have something about them that is “different,” is that difference all that meaningful?
What does Screwtape mean when he says “The game is to have them all running about with fire extinguishers whenever there is a flood?”

Letter 26
What is the problem confusing ‘Charity’ with ‘Unselfishness?’
Why would it be a “great point gained” to Satan when “a man surrenders benefits not so that others may be happy in having them but so that the man can be unselfish in giving them?”
Why might selfishness be less damaging than unselfishness? That is, What is the “Generous Conflict Illusion” that Screwtape discusses?

Letter 27
What is the “heads I win, Tails you lose” argument Screwtape proposes using against the human regarding prayer?
Have you ever thought this way about prayer? If so, what have you done about it?

Letter 28
Screwtape says “Prosperity knits a man to the World. He feels that he is ‘finding his place in it,’ while really it is finding its place in him.” How does a person and the world get “knitted together?” What is the bond, or “knit?” That is, what things draw us to the world?
Screwtape tells Wormwood, “Do not let us be infected by our own propaganda.” What propaganda is he referring to?
Screwtape actually suggests that the demons are trying to keep the man safe! Why is that?
How does Screwtape propose attacking middle-aged adversity? How is this different than attacking middle-aged prosperity?
Why does Screwtape want the human to pursue: Worldly Advancement? (Phil 4:19)
Prudent connections? (2 Cor. 6:14-17)
Safety First? (Matt. 6:27)

Letter 29
Why, according to Screwtape, did God create a dangerous world?
Screwtape says that both “courage” and “cowardice” are “undisguisable” How does being undisguisable help the human “awake from their moral stupor? That is, what specifically does undisguise-ability do for us?

Letter 30
What are the two ways in which the word “real” can be used?
How can it be used against us, according to Screwtape?

Letter 31
What, ultimately, happens to the patient?

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