Screwtape Letter #14 – Questions

Letter #14

This is the first letter after the patient’s second conversion.

Things don’t appear to be getting any better from Screwtape’s point of view.



My dear Wormwood,

The most alarming thing in your last account of the patient is that he is making none of those confident resolutions which marked his original conversion. … This is very bad.

I see only one thing to do at the moment. … But don’t try this too long, for fear you awake his sense of humour and proportion, in which case he will merely laugh at you and go to bed.

14.1) It has been said that “virtue is the middle path between two extremes”. How does this fit in with the patient’s new attitude about promises and expectations?

At the same time, Screwtape appears to see the patient’s new virtue as either going the way of something “very bad” or as a small window of opportunity. What two extremes is Screwtape looking at?





But there are other profitable ways of fixing his attention on the virtue of Humility. … above all, if self-contempt can be made the starting-point for contempt of other selves, and thus for gloom, cynicism, and cruelty.

You must therefore conceal from the patient the true end of Humility. … And since what they are trying to believe may, in some cases, be manifest nonsense, they cannot succeed in believing it and we have the chance of keeping their minds endlessly revolving on themselves in an effort to achieve the impossible.

14.2) Screwtape seems to be on a roll now. At first there was only one thing to do. Now, he sees other ways for Wormwood to attack.

In what ways is this renewed attempt to conceal reality from the patient typical of Satan’s attacks on us?

Do you see any repetition of tactics and / or lack of originality that could lead the patient to “merely laugh at <Wormwood> and go to bed”?





To anticipate the Enemy’s strategy, we must consider His aims. …  He really loves the hairless bipeds He has created and always gives back to them with His right hand what He has taken away with His left.

14.3) Screwtape now returns to discussing the ways of God the Father.

Screwtape starts off with a pretty good explanation of how God wants to transform us. His own contempt for both us and God come through loud and clear by the end.

He has come a long way from the small window of opportunity at the beginning of the letter. How has Satan’s own pride influenced both the direction of the argument and Screwtape’s ability to “think clearly”?





His whole effort, therefore, will be to get the man’s mind off the subject of his own value altogether. … Even of his sins the Enemy does not want him to think too much: once they are repented, the sooner the man turns his attention outward, the better the Enemy is pleased,

Your affectionate uncle


14.4a) After his outburst at the end of the previous paragraph, Screwtape gets back to the original theme of this letter.

Screwtape has returned to some level of trying to provide useful assistance to Wormwood – as opposed to just a tirade against humans and God.

However – there’s a problem here. If God really won’t let things alone, if He insists on bringing in the “dim uneasiness” – what help has Screwtape given to Wormwood? Where has he fallen short?





14.4b) How might the balance be swung one way or the other?






No more lavish promises of perpetual virtue, I gather; not even the expectation of an endowment of ‘grace’ for life, but only a hope for the daily and hourly pittance to meet the daily and hourly temptation! This is very bad.

Endowment – an attribute of mind or body; a gift of nature.

In this case – a gift from God.

Pittance – a small allowance or sum, as of money for living expenses.



All the abjection and self-hatred are designed, in the long run, solely for this end; unless they attain this end they do us little harm; and they may even do us good if they keep the man concerned with himself, and, above all, if self-contempt can be made the starting-point for contempt of other selves, and thus for gloom, cynicism, and cruelty.

Abjection – the condition of being servile, wretched, or contemptible

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