Screwtape Letters discussion questions - Letter 1

Screwtape Letters
discussion questions - Letter 1
1. At the end of the first paragraph of letter one, Screwtape says it’s best not to try to persuade
people with the question of what is true or false, because truth is not the thing people are most
concerned with. What are the things he says people are more concerned with than truth, and
why is this so?
2. What are some specific examples of things Christians are tempted to prioritize over the truth—
or over authentic discipleship—and how does this problem show itself in the local church?
3. In the last three sentences of paragraph two, Screwtape says Wormwood’s business should be
to keep people from “attending to universal issues,” and to fix a person’s attention on the
“stream of immediate sense experiences.” He tells Wormwood to lead the patient to think of
those immediate sense experiences as “real life.” Then he adds, “don’t let him ask what he
means by ‘real.’ ”
How does this parallel Luke 10:38-42 and Matt. 13:18-23?
4. Consider the following two conversations:
a) A discussion with your spouse about financial planning and weekly errands.
b) A discussion about the importance of prayer and its effects on us.
Which of these two would you be more likely to think of as a conversation about “real life”
and why?
5. Why is a sense of the “ordinariness of things” such an ally to Screwtape and his cause?
Screwtape Letters
discussion questions - Letter 2
1. Why does Screwtape say all our habits of body and mind are still in his favor, even after we
become Christians?
2. In the second paragraph Screwtape’s comments on the “pictorial” rather than the “spiritual”
thinking of his “patient.” Another way to say this could be a distinction between image and
substance, or appearance and reality.
What is an example of something that could deepen our relationship with Christ, but could also
be missed because of an unappealing image or appearance?
3. What is a specific example of something in our Christian journey that “marks the transition from
dreaming aspiration to laborious doing”?
4. Why does Screwtape say we are less vulnerable to temptation when we are less dependent on
emotion?
5. Explain in your own words the main idea expressed in Screwtape’s comment in the last
paragraph about the relationship between the truth of Christianity and the hypocrisy of
Christians?
Screwtape Letters
discussion questions - Letter 3
1. Why is it to Screwtape’s advantage for a Christian to think of conversion as something
primarily “inside” himself?
2. Why does Screwtape like it when someone prays only for another person’s soul?—what does
he seek to achieve with this?
3. What is the “double standard” Screwtape encourages between the patient and his mother?
4. At the end of the letter Screwtape asks if the mother is jealous of the “new factor in her son’s
life,” meaning his recent conversion. Explain the particular problem with a person that causes
jealousy over a loved one becoming a Christian—as is the case with the older brother in the
parable of the prodigal son.
Screwtape Letters
discussion questions - Letter 4
1. Why does Lewis warn us about, “a vaguely devotional mood in which real concentration of will
and intelligence have no part”? Why would such an attitude in our prayer time be pleasing to
Screwtape?
How significant is the physical posture you take when you pray? Why?
2. At the end of the second paragraph, Screwtape says, “It is funny how mortals always picture
us as putting things into their minds: in reality our best work is done by keeping things out.”
Name one fact Screwtape would want to keep us from realizing and explain why.
3. In Acts 12:11-19, in Peter’s miraculous release from prison and the response of those praying at
the house of Mary, the mother of John-Mark, we see a clear example of a response to prayer
which was completely unexpected—presumably not anticipated in the feelings of those praying.
4. What lesson is there to learn from this when we consider Screwtape’s remarks in the third
paragraph about the attempt to generate certain feelings through prayer?
5. What does Screwtape mean when he says about God, “He is cynically indifferent to the dignity
of His position, and ours, as pure spirits.”?
6. Note the last two sentences of the letter: “The humans themselves do not desire it—[true
exposure of one’s self in God’s presence]—as much as they suppose. There’s such a thing as
getting more than they bargained for!”
7. What does he mean in saying some are afraid to get “more then they bargained for” in prayer?
Has this ever happened to you?
Screwtape Letters
discussion questions - Letter 5
1. How can both patriotism and pacifism lead people away from God?
2. What is God’s “blockade” keeping from Screwtape and other demons?
3. What does Screwtape mean by “this present phase of the great conflict”?
4. Note the following statement about God’s treatment of those on the wrong side of an issue:
“He often makes prizes of humans who have given their lives for causes He thinks bad on the
monstrously sophistical ground that the humans thought them good and were following the
best they knew.”
What are some specific examples where this would be true and some where it would not be
true?
5. Why is it better for people to die in war rather than in old age in nursing homes?
6. Why is it the case that “a faith which is destroyed by a war or a pestilence cannot really have
been worth the trouble of destroying”?
Screwtape Letters
discussion questions - Letter 6
1. How do suspense and anxiety “barricade” a person’s mind against God? (Consider the last
sentence of the first paragraph)
2. When does Screwtape say he wants a person to be reflective of his own emotions and when
does he want a person to forget about his own feelings and focus only on the object of his
attention? Why is this the case?
3. How does Screwtape get the patient to the point where his malice is real and his beneficence
is imaginary? (paragraph 5)
4. Lewis uses the illustration of three concentric circles to illustrate the make up of a person:
intellect
fancy
!
!
will
He says a person is only authentically living the Christian life when “[virtues]
reach the will and are there embodied in habits.” Why is Screwtape not threatened
by a person’s Christianity resting on the two outer circles of intellect and fantasy
(perhaps we could add another outer circle for emotion)?
5. In considering the will, what do you think is the difference between “the conscious fume and
fret of resolutions and clenched teeth” and “the real center, what [God] calls the Heart.”?
Screwtape Letters
discussion questions - Letter 7
1. Why would it be easier (or more preferable) for someone to believe in the existence of
demons, but not in God?
2. Explain the flaw of reasoning Screwtape points to in saying that if a man cannot believe in a
devilish cartoon character with red tights, he cannot believe in devils or demons at all.
3. Why does Screwtape say, “All extremes except extreme devotion to the Enemy are to be
encouraged”?
4. What is a specific example you have seen, or a vulnerability you foresee, of Christians
acquiring, “the uneasy intensity and the defensive self-righteousness of a secret society or a
clique”?
5. In what ways are we tempted to see “the World an end and faith a means”, and why is this
such a bad thing?
6. In your own words, explain what type of religion makes a person “more securely” a possession
of Screwtape?
Screwtape Letters
discussion questions - Letter 8
1. Why is it the case that God “relies on the troughs even more than on the peaks” in our lives to
grow us into the people he wants us to be?
2. What is meant by saying God “cannot ravish. He can only woo”? What does this tell us about
God’s character and about the nature of our relationship with him?
3. What is a specific example of a situation in your life where you have had to “carry out from the
will alone duties which have lost all relish”?
4. What are some specific examples of problems that arise when people’s behavior and decisionmaking are driven only by the “relish”—the emotional highs and physical pleasures—and not
by the sheer will to do what is right?
5. When someone “no longer desiring, but still intending, to do [God’s]will, looks round upon a
universe from which every trace of Him seems to have vanished, and asks why he has been
forsaken, and still obeys,” that person makes a very clear statement about what he thinks
about God. In your own words, what does this type of obedience say about a person’s view of
God?
Screwtape Letters
discussion questions - Letter 9
1. Screwtape says one of the most effective ways to tempt people going through a “trough,” or
dry period is through sex. The concept here is that people seek sex as a means of distraction
or comfort in times of stress and/or emptiness. With this in mind, how often do you think sexual
sin—and sin in general—is pursued as a remedy to boredom or as a means of numbing
oneself to the problems and emptiness of life?
2. Why is it the case that sex and other pleasures are different in quality when pursued as a
remedy for the “trough” period rather than when they are enjoyed in the “peak” periods?
3. What insight can we gain from this letter on healthy Christian perspective on sexuality?
(Consider in your answer the meaning of the Christian virtue of chastity—which is not the
same as “abstinence.”)
4. What is Screwtape’s particular strategy for using pleasure to corrupt people?
5. Why is it a bad thing for a person to try to recover “by sheer will power” the elated feelings that
came with a past Christian experience?
6. Why does Screwtape say, “A moderated religion is as good for us as no religion at all”?
7. Why is it so important that Screwtape rely on “jargon, not reason”?
8. Why is it so important that Screwtape keeps “[a person’s] mind off the antithesis between True
and False”?
Screwtape Letters
discussion questions - Letter 10
1. What does it mean to be “superficially intellectual, and brightly skeptical about everything in the
world”?
2. What is a good example of a popular idea or movement that’s promoted more because it’s
fashionable than because it is true?
3. Have you ever been silent when you should have spoken, or laughed when you should have
been silent?
4. Screwtape says the Church in the 20th century has given little emphasis to its separateness
from the world. It’s usually easy to see how this concept can be abused (making church an
exclusive club, looking down upon outsiders, etc.), but what is a good, concrete example of
how the Church is to be separate from the world? In other words, what is a right application of
2 Corinthians 6:14-18 and 1st John 2:15-17?
5. In saying that a person can be made to “realize the character of [his] friends only while they
are absent,” and that “their presence can be made to sweep away all criticism,” Lewis points
out the tendency to place a higher value on politeness, social harmony, and positive feelings,
than on real virtue and moral character.
What are some consequences that could result from this type of misplaced value, and how can
we make ourselves less vulnerable to operating this way in our relationships with others?
6. In light of the next to last paragraph, explain how the person in question is guilty of pride or
haughtiness.
Screwtape Letters
discussion questions - Letter 11
1. How can people “progress quietly and comfortably” towards Hell without ever committing any
“spectacular crimes”?
2. What does it mean to be a “scoffer” and why is this sinful?
3. In your own words, explain what Lewis is saying about the nature of joy in the second
paragraph.
4. What’s a specific example of humor destroying shame?
5. How does a habit of flippancy build up around someone an armor plating against God?
Screwtape Letters
discussion questions - Letter 12
1. Why is it important to Screwtape that the person he’s trying to tempt thinks the choices that
have moved him away from God are “trivial and revocable”?
2. How does a person move away from God while participating in church and other explicitly
Christian activities?
3. Have you ever resisted God the way a man in financial trouble resists looking at his bank
book?
4. In this letter Lewis addresses the problem/sin of listlessness or indolence—a lethargic state
characterized by an absence of vigor, attention and will. This could also be synonymous with
many cases of what’s often referred to as “depression.” For the person in question in this letter,
what is the cause of the indolence? Do you think the same issue could be the cause of a lot of
“depression”?
5. How does the idea that God is the one “without whom nothing is strong” apply in our everyday
lives? Also, how does this apply to our big decisions and overall track in life?
6. How can we be best guarded against “the safest road to Hell…the gradual one—the gentle
slope, soft underfoot, without sudden turnings, without milestones, without signposts.”?
Screwtape Letters
discussion questions - Letter 13
1. What do you think of the idea of a “second conversion”? Have you ever had an experience you
would describe with that phrase?
2. Screwtape refers to a person’s submission to, and awareness of the presence of God as an
“asphyxiating cloud” and says those who are surrounded by it are inaccessible to him and
other demons? How does a person get to the point of being permanently surrounded by the
presence of God?
3. Can you think of a time when you did something that was supposed to be pleasurable, not
because you liked it, but because it was expected of you, or because you wanted to impress
someone else?
4. What are some specific examples of how the larger culture tries to sell us, “vanity, bustle, irony,
and expensive tedium as pleasures”? How can we guard ourselves against this?
5. According to Screwtape, what is the difference in the ways in which God and Satan want to
detach people from themselves?
6. Consider the following quote: “The deepest likings and impulses of any man are the raw
material, the starting-point, with which the Enemy has furnished him.” What does it say about
the character of God if the good things we like most deeply are a starting point from which we
move toward him?
7. At the end of the letter, Screwtape says, “Let [the human] do anything but…” Anything but
what? Why is this so important?
Screwtape Letters
discussion questions - Letter 14
1. Why does Screwtape like it when a person makes “confident resolutions” upon his conversion
experience? (He says in the first paragraph that he’s alarmed by the fact that the person has
not made such resolutions)
2. Have you ever experienced the cycle Screwtape describes in the second paragraph?
3. In the third paragraph, how does Screwtape say virtuous behavior can be of use to his cause?
4. How does Screwtape say a false sense of humility works in a woman who really is pretty or a
man who really is clever/intelligent? What, specifically, is bad about this?
5. What does it take to achieve that perfect balance point where we can have the same
enjoyment and appreciation of an excellent work, regardless if we or someone else created it?
6. In the last paragraph, Screwtape says, “Your efforts to instill either vainglory or false modesty
into the patient will therefore be met from the Enemy's side with the obvious reminder that a
man is not usually called upon to have an opinion of his own talents at all, since he can very
well go on improving them to the best of his ability without deciding on his own precise niche in
the temple of Fame.”
Do you ever find yourself trying to assess your self worth by comparing your talents and
accomplishments with those of other people? If your value as a person is not seated in your
talents and accomplishments—in your “niche in the temple of Fame”—what does give you
value?
7. How does the last paragraph in this letter relate to the conversation between Jesus and Peter
in John 21:18-22?
Screwtape Letters
discussion questions - Letter 15
1. What does this statement mean: “The present is the point at which time touches eternity”? In
other words, Lewis says our experience of the present—in contrast to the past or future—is
most like eternity. Why is this so?
2. Why does Screwtape say the future is the thing least like eternity?
3. Have you ever placed on “the alter of the future” gifts meant for the present? How? Why is this
such a temptation and what are the consequences?
4. In the last paragraph, what does Lewis (through Screwtape) tell us we should pray for
regarding the future, instead of placing all our hopes in the belief that the future will be
agreeable and will contain no “horrors”?
5. Philology is the study of language and the meaning and usage of words. Why do you think
Screwtape and the other demons are so interested in Philology? He even says Hell has a
“Philological arm” (or Philology department).
Screwtape Letters
discussion questions - Letter 16
1. Lewis wrote The Screwtape Letters almost 60 years ago. Do you think the problem of people
being a “taster or connoisseur of churches” has gotten better or worse since then? Why does
Screwtape encourage people to go to many different churches instead of remaining loyal to
one?
2. In the second paragraph, what is the difference between church being a unity of place not a
unity of likings? In other words, what should unify people attending church together if not their
tastes and likings?
3. In what areas are you most tempted to be a critic when God wants you to be a pupil (or
student)?
4. Screwtape says he likes a pastor whose teaching, “revolves endlessly round the little treadmill
of his fifteen favorite psalms and twenty favorite lessons,” so that a “truth not already familiar to
him and his flock” won’t get through. What is an example of an underemphasized, but
important Biblical doctrine—one you rarely hear a sermon on?
5. Why is it important that Screwtape says he doesn’t depend on the doctrines of the Church to
create malice? What types of things within church does Screwtape use to divide people and
draw them away from God?
6. The problem Lewis describes in this chapter is a very poignant one today: On the one extreme
there are churches who hold hard and fast to their tradition for its own sake, making no effort to
accommodate the curiosities and sensibilities of newcomers. On the other extreme are
churches who “market” their services to people, trying to make the worship experience as
attractive as possible to the point where it ceases to be worship and becomes only
entertainment.
What are some guiding principles that will enable us to keep a balance between these two
extremes?
Screwtape Letters
discussion questions - Letter 17
1. What is the difference between gluttony of delicacy and gluttony of excess?
2. Why is it important to note that the work of demons is described as “quiet” and “unobtrusive”?
3. According to this letter, the real problem (that Screwtape is happy with) with gluttony is not
necessarily in what or how much a person eats. What, then, is the real issue at the heart of
gluttony?
4. Why is vanity in his patient not enough for Screwtape, but rather vanity “gradually turned into
habit”?
5. What are some examples of “indulgences” or luxuries we have come to see as rights so that
we feel cheated if we are deprived of them?
Screwtape Letters
discussion questions - Letter 18
1. Screwtape says he wants people to think of the feelings of being in love as the only grounds
for marriage, so that when that feeling is absent, a marriage is no longer binding. What should
a marriage be based on (and bound by) if not only on the feeling of being in love?
2. What insight does Lewis give in this letter about the Trinity? Does this change your
understanding of that doctrine?
3. Screwtape says the whole philosophy of Hell is based on the principle of competition, so that
every time someone gains something, it must come at the expense of someone or something
else. How is this different from his description of God's plan, particularly in relation to the
family?
4. Screwtape says religious emotions often, but not always, come with a conversion experience.
What more does a genuine Christian conversion experience consist of than just emotions?
5. In the following statement from Screwtape, Lewis gives us his views on the proper motives for
marriage. His understanding of marriage (and many others’ in centuries past who also held
Lewis' view) is often very different from the way we typically think about it. How does this
statement strike you? Do you agree or disagree? Why? Explain:
“humans who have not the gift of continence (or celibacy) can be deterred from seeking
marriage as a solution because they do not find themselves 'in love', and, thanks to us, the
idea of marrying with any other motive seems to them low and cynical. Yes, they think that.
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.”
Screwtape Letters
discussion questions - Letter 19
1. Screwtape (and all of Hell) cannot accept the reality of God’s disinterested love. Because of
this, Screwtape is cynical and is always trying to find out what God is “really up to.” Have
you ever missed out on something wonderful because of cynicism and mistrust of another
person?
What is a key to finding balance between healthy skepticism and hard-hearted cynicism?
2. Cynicism has the effect of hardening people on the inside so that—if it goes far enough—
the cynic is unable to trust anyone because he’s always looking for “what’s behind” the
other person’s words or actions, no matter what the other is intending.
What insight does this give on how people can go to Hell even though God is all loving and
all powerful?
3. What exactly does Lewis mean by saying (through Screwtape), “Like most of the other
things which humans are excited about, such as health and sickness, age and youth, or
war and peace, [falling in love] is, from the point of view of the spiritual life, mainly raw
material”?
4. How does the answer to number three affect they way we think about suffering and
hardships?
Screwtape Letters
discussion questions - Letter 20
1. Have you ever given in to temptation because you thought doing so was the only way to
get past it? If so, what are your thoughts in retrospect?
2. Define chastity (It’s not the same as abstinence).
3. Speaking about “tastes” for what people do and do not find attractive in the opposite sex,
what does Screwtape say is the strategy used on changes in the fashion industry?
4. Explain the irony in the modern idea of being “ ‘frank’ and ‘healthy’ and getting back to
nature.”
5. Screwtape seeks to make the “role of the eye in sexuality more and more important.” If the
role of the eye (physical appearance) in sexuality is exaggerated, what is its appropriate
role, and what else should be involved in sexual attraction?
6. What is a good, modern example of the false concept of “irresistible and all-excusing Love,”
and what are some negative consequences that can come from it?
7. How can we most effectively teach our children chastity rather than only abstinence?
Screwtape Letters
discussion questions - Letter 21
1. What’s a specific example of someone being easily tempted because of the “darkening [of]
his intellect”?
2. Why are our claims of possession so tenacious and hard to get rid of? In other words, why
is it so often hard for us to realize that our time, money, even loved ones, are not “our
own”?
3. Consider the following passage:
If the Enemy [God] appeared to him in bodily form and demanded that total service for even
one day, he would not refuse. He would be greatly relieved if that one day involved nothing
harder than listening to the conversation of a foolish woman; and he would be relieved
almost to the pitch of disappointment if for one half hour in that day the Enemy said, “Now
you may go and amuse yourself.” Now if he thinks about his assumption for a moment,
even he is bound to realize that he is actually in this situation everyday.
What’s an example in Scripture of God leading someone to do something in which the
person being led saw no purpose? How often might this happen in our own lives?
4. What’s a good example of an idea(s) commonly held in the minds of people in the Church
(or outside it) that lies “silent, uninspected, and operative”?
5. As is the case in Screwtape’s point about the different meanings of the word “my,” the
problem of a false sense of ownership is a big factor in corrupting people’s capacity to love
each other—as when someone begins to think of the ownership implied in the statements
“my boots,” “my servant,” and “my wife” all the same way.1
How is this tendency towards possession, ownership, entitlement, etc. related to the sin of
pride? How might it be related to the sin of idolatry?
6. Do you think this letter might speak more acutely to American Christians than to those in
most other countries? Why?
1
The issue of love corrupted by possessiveness is one of the main themes in Lewis’s novels Till We Have Faces and The Great
Divorce.
Screwtape Letters
discussion questions - Letter 22
1. Why is Screwtape so frustrated (and God so pleased) with the woman he describes as, “A
two-faced little cheat who looks as if she’d faint at the sight of blood, and then dies with a
smile.” ?
2. How does the idea of God being a Hedonist strike you? What would you say to someone
who asks, “How can God be a hedonist when he allows people to get cancer and children
to die of starvation?” (In answering, consider the end of paragraph three at the sentence
beginning “Everything has to be twisted…”)
3. In paragraph four, Screwtape says the women’s family home “reeks of that deadly odor,”
meaning the family and the household are characterized by righteousness, peace and joy
in the Holy Spirit. He also says this rubs off on those who visit.
Along the same lines, listen to Lewis’ description of Sarah Smith in chapter 12 of The Great
Divorce: “Few men looked on her without becoming, in a certain fashion, her lovers. But it
was the kind of love that made them not less true, but truer, to their own wives.”
Have you ever known someone who was so transformed by Christ, so saturated with the
Holy Spirit, that just being in the person’s presence made you better in some way?
4. Why does Screwtape hate both Music and Silence?
5. Screwtape says noise keeps the demons from having to worry with “scruples, and
impossible desires.”
In what ways can a concern for expediency and a general busy, noisy environment hinder
moral decision making?
In what ways can these things dull our deepest and most importance desires?
Screwtape Letters
discussion questions - Letter 23
1. What is a good contemporary example of a false but popular picture of Jesus that is
produced by suppression of one part of Scripture and exaggeration of another?
2. Lewis makes a big point about the scholarly guessing “on which no one would risk ten
shillings in ordinary life,” but still brings much fame and book sales to the guessing
scholars. Spend a few minutes doing a web search on the Jesus Seminar.
What do you think of the methods of and motives for their research on the “historical
Jesus”?
3. How do we know the picture of Jesus given in the New Testament is historically accurate?
4. Do you find it surprising that Jesus’ moral teaching was very similar to that of many
influential teachers like Socrates or Confucius? If much of Jesus’ moral teaching was
similar to other religious and philosophical leaders, what makes Jesus different?
5. Approximately twenty lines up from the bottom of the third (long) paragraph, note the
section beginning with the sentence “For the real presence of the Enemy…” In this
passage, Screwtape gives insight to the motives that drive many liberal scholar’s quest for
the “historical Jesus.”
Why would Jesus being “a leader acclaimed by a partisan” or “a distinguished character
approved by a judicious historian” be more appealing to some people than the thought of
him being a God to be worshiped?
6. What do you think of the statement that the Gospels were not written primarily to make
Christians, “but to edify Christians already made”?
7. Through Screwtape, Lewis warns us about using Christianity as a means—even a means
to good things like social justice. In what ways are we vulnerable today to seeing our faith
in Christ as a means to gain something else (even something good) instead of an end in
itself?
Screwtape Letters
discussion questions - Letter 24
1. What is a good example of something Christians often think of as a conviction, but really
is just, “color we have taken from [our] surroundings”?—In other words, what’s
something we think of as “the right way,” when really it is only the way we’ve been taught?
2. As a general rule, would you say Christians are a better grade or kind of people than nonChristians? Why or why wouldn’t this be an accurate thing to say?
3. What groups of Christians are more prone to think of themselves as superior to other groups of
Christians?
4. When and over what have you experienced a sense of “sly self-congratulation”?
5. In this letter, Lewis (through Screwtape) warns us about Christianity becoming a clique, both
separate from the unbelieving world and from other groups of Christians. What, specifically, is the
vice that feeds our desire to be in an inner circle or clique?
6. Are you surprised by Screwtape’s comments at the very end of the letter on the people who are
killed by bombs? What insight on death is given in these comments?
Screwtape Letters
discussion questions - Letter 25
1. Why do many people have a “horror of the same old thing”?
2. What is the correlation Screwtape makes between gluttony and a desire for change?
3. How is the demand for novelty a dangerous thing in the realm of ethics—in counseling people
struggling with moral issues?
4. In what ways have you seen a demand for novelty (a fear of the “same old thing”) influence
movies, TV and music?
5. What point is Lewis making in Screwtape’s comment: “The game is to have them all running
about with fire extinguishers whenever there is a flood, and all crowding to that side of the boat
which is already nearly gunwhale under.”?
6. Screwtape says the Enemy (God) wants people to ask very simple questions about important
issues and decisions: “Is it righteous? Is it prudent? Is it possible?” But Screwtape would rather
people ask if something is in accordance with “the movement of our time?” or “Is this the way
History is going?”
In our culture today, what is an issue on which people’s thinking is often driven by a concern
for what’s popular and what’s in accordance with the movement of the time, rather than what is
wise and right?
7. What’s a good modern example of an emotionally charged word or phrase that is used in place
of a more neutral word in order to manipulate people’s thinking?—as with the example of
substituting “stagnant” for the more neutral “unchanged”?
Screwtape Letters
discussion questions - Letter 26
1. In what ways is the word “Love” used ambiguously? What are some examples of decisions or
actions that are said to be done “out of love,” but really are motivated by something else?
2. Have you ever done something for someone else, not for that person’s sake, but so that you
could be considered “unselfish”?
3. According to Screwtape, what is the difference in the way men and women perceive
selfishness?
4. In your own words, explain the main point in the third paragraph about the problems that come
from the illusions created by sexual attraction.
5. Screwtape makes a big point about the games people play, with one person trying to be more
“unselfish” than the other, while really only trying to manipulate the other in order to make
himself feel righteous.
How do we avoid this problem? What is the Christian way of handling disagreements (even
small ones)? What insight do we gain on this from what Jesus says in
Matthew 5:33-37?
Screwtape Letters
discussion questions - Letter 27
1. What is it that Screwtape does not want a person to do with a distraction or sin? Why—what
will happen if a person does this?
2. Why are we sometimes tempted to offer lofty, pious-sounding prayers in situations where God
wants us to ask for our daily bread and the healing of our sick?
3. What is the “heads I win, tails you lose” argument Screwtape describes? Why is this
important?
4. What is the connection between freewill and love?
5. In light of Screwtape’s point about learned men, in your own words, explain the difference
between intelligence and wisdom.
6. There are many very relevant and very important points of application for the following
statement:
“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 rejected as
unutterably simple-minded.”
This is true about the way many people read the Bible and other ancient texts.
Why is this so?
7. What does Screwtape say makes a “free commerce between the ages,” and why does he want
to prevent this?
Screwtape Letters
discussion questions - Letter 28
1. What is Screwtape concerned with much more than with “the death of men and the destruction
of cities”?
2. Why does Screwtape want so badly to keep his “patient” alive?
3. Why does Screwtape say people regard death as the prime evil and survival as the greatest
good?
4. Why does Scrwtape say it is best for his cause if the patient’s middle-aged years are
prosperous?
5. Screwtape says he wants people to apply themselves steadily toward “worldly advancement,
prudent connections, and the policy of safety first.”
In contrast, what would be a good list of the things God wants us to apply our lives to?
6. What is a good example of someone or group of people seeking to turn earth into Heaven in
attempt to achieve heaven without God?
7. What does the following statement mean:
“where Virtue is concerned ‘Experience is the mother of illusion’ ” ?
8. Upon reading the last paragraph, what is your first thought in response to the percentages of
people who live to what we typically think of as a “normal” elderly age? What do you think is
behind your gut-level response to this paragraph? Why do you feel the way you do when first
considering it?