The Wormwood Files

A companion series to C.S. Lewis’s The Screwtape Letters — one “Dear Wormwood” post per letter, exploring how ordinary, routine circumstances become the devil’s actual instruments.

  • Dear Wormwood #12 — The Gentle Slope

    This might be the most important letter in the whole book for what our series has been tracing. Screwtape’s only real worry is that Wormwood, hurrying things along, might accidentally wake the patient up to what’s actually happening to him. Because the two of them can see the real trajectory clearly — a slow drift…

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  • Dear Wormwood #11 — The Uses of Laughter

    The patient’s new social circle laughs a lot, Wormwood reports, and Screwtape wants to correct a rookie mistake before it costs them anything: laughter is not automatically useful to hell. It matters enormously what kind. Screwtape sorts human laughter into four categories, and rates each one for tempting purposes. Joy — the helpless laughter of…

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  • Dear Wormwood #10 — Two Parallel Lives

    Screwtape is delighted: the patient has made some new friends — a rich, fashionable, brightly skeptical couple who belittle everything with practiced ease. Nothing dramatic happened to draw the patient in. No argument, no seduction, no crisis of faith. Just an office acquaintance and, Screwtape notes approvingly, a subtle play of looks, tones, and shared…

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  • Dear Wormwood #9 — Just a Phase

    Screwtape follows up on the Law of Undulation with practical instructions: now that Wormwood understands the trough the patient is in, how exactly does he exploit it? Two routes, and both are worth sitting with. The first is bodily. Counterintuitively, Screwtape says the trough — not the peak — is the best time for temptations…

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  • Dear Wormwood #8 — The Law of Undulation

    Wormwood reports, hopefully, that the patient’s religious enthusiasm seems to be fading — and Screwtape responds with real exasperation at his nephew’s inexperience. Doesn’t anyone teach the basics anymore? He’s talking about what he calls the Law of Undulation, and it’s one of the most important ideas in the whole book. Humans, Screwtape explains, are…

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  • Dear Wormwood #7 — When the Cause Becomes the Religion

    Wormwood apparently asked whether the patient needs to stay ignorant of devils existing at all, and Screwtape explains hell’s current strategy: stay hidden, for now. It’s a real dilemma for them — believers in devils make bad materialists, and materialists lose the visceral terror direct belief could produce. Screwtape’s dream is something subtler: people who…

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  • Dear Wormwood #6 — Love the Distant, Resent the Near

    The patient might get called up for military service — or might not — and Screwtape is delighted by exactly that uncertainty. He doesn’t want Wormwood to push the patient toward fear of any one specific outcome. He wants the man’s mind stuffed with contradictory pictures of the future, all at once, because pure suspense…

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  • Dear Wormwood #5 — Why War Doesn’t Help Hell

    Wormwood writes in “delirious with joy” — a European war has just broken out, and the patient has had a sleepless, terrified night over it. Screwtape’s response is almost fatherly, and a little contemptuous: you’re not delirious, he says, you’re drunk — drunk on your first real taste of a human soul’s anguish, and it’s…

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  • Dear Wormwood #4 — Praying to the Ceiling Corner

    Screwtape opens this letter annoyed — Wormwood’s advice about the mother backfired, and rather than take responsibility, he tried to pin it on his uncle. Screwtape isn’t having it, and moves straight into what he clearly considers the real subject at hand: how to handle a patient’s prayers. The best outcome, if it can be…

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  • Dear Wormwood #3 — The Lift of an Eyebrow

    Screwtape is delighted with how things are going at the patient’s mother’s breakfast table, and he wants Wormwood to press the advantage fast, before the new Christian faith starts spreading outward into how the patient actually treats her. His instructions here are some of the most domestic — and most uncomfortably recognizable — in the…

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  • Dear Wormwood #2 — The Squeaky Boots in the Next Pew

    Bad news for Wormwood, and Screwtape says so plainly: the patient has become a Christian. But Screwtape doesn’t panic, and that’s the real lesson of this letter. Plenty of new converts get reclaimed, he says, after only a brief stay in the Enemy’s camp — all the old mental and bodily habits are still working…

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  • Dear Wormwood #1 — The Bus and the Newsboy

    The first letter opens with Screwtape mildly annoyed at his nephew. Wormwood, it turns out, has been steering his patient toward materialist friends and letting him read arguments against Christianity, on the theory that a good debate is the way to talk a man out of his faith. Screwtape thinks this is amateur hour, and…

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