Wormwood’s patient has made new friends: “just the sort of people we want him to know—rich, smart, superficially intellectual, and brightly skeptical about everything in the world” (49). Screwtape sees the opportunity to play on the young man’s vanity and have him live a double life wherein he spends Saturday with his entertaining friends engaged in “bawdy and blasphemy over coffee” (52)and then goes to church on Sunday with the “grocer” who is beneath him. 

This chapter focuses on human laughter and humor. Screwtape tells Wormwood that “Humour is for them the all-consoling and (mark this) the all-excusing, grace of life. Hence it is it is invaluable as a means of destroying shame . . . Cruelty is shameful—unless the cruel man can represent it as a practical joke” (55). Screwtape is thus very pleased that the young man’s new friends engage actively in humor and joking.  

Screwtape believes the young man is probably in a state of uneasiness and “half-conscious guilt” over his lifestyle with his new friends conflicting with his religious observances. This is the kind of distraction from true devotion and faithfulness that the devils wish to foster.