Christian does not leave Vanity alone, for Hopeful had been inspired by Faithful's steadfast faith and thus decides to accompany Christian. Not long after they set out from Vanity, they run into By-ends. By-ends hails from the rich town of Fairspeech, and he has done well for himself materially. He is married to the virtuous daughter of the Feigning family. He tells the two men that his religion never goes "against wind and tide", because his faith is not quite so strict. Christian has heard of this "knave" before and tells him will be problematic if he wishes to come with them, because they will most certainly be going against wind and tide.
Christian and Hopeful leave him, but they look back and see him meeting Mr. Hold-the-World, Mr. Money-love, and Mr. Save-all. These men had been at school with Mr. By-ends, where they had learned the "art of getting." The men talk among themselves, trying to justify a religion of conforming and materiality, criticizing Christian and Hopeful for being too righteous for their own good. The men bring their justification to Christian and Hopeful to see if they agree. Christian is a dissenter, stating that "it be unlawful to follow Christ for loaves" (120). He cites John 6:1-60, in which Jesus calls himself "the living bread which came down for heaven: if any man eat of this bread, he shall live forever." He then offers examples of men who became religious for the wrong reasons, and they were heathens and were punished. The four schoolmates are stumped, and Christian and Hopeful move on.
They move through a plain called Ease, and then up a small hill, on the side of which is a silver mine. Many other pilgrims have gone into the mine and died there. The mine is run by a man called Demas, and he tries to persuade the pilgrims to stop and mine for silver. Christian has heard of the dangers of this place and is weary. He also knows that Demas' father, Judas, was hanged as a traitor, and the two move on past the mine. By-ends and his companions are taken in, however, and they fall over the precipice into the pit, never to be seen on the way again. On the other side of the mine and the plain, Christian and Hopeful see a pillar that they take to by Lot's wife, who was transformed into a pillar of salt because she looked back 'with a covetous heart when she was going from Sodom for safety" (128). Hopeful and Christian see the pillar as a sign of caution to them as they go on their journey.
The men come to the River of God and drink the refreshing water, eat the juicy fruit, and stock up on leaves for medicine before taking a nap on the nearby meadow. After they recommence along the way, they arrive at By-path Meadow, which provides a route running alongside the main path. Christian convinces Hopeful to take the path with him, as it looks easier. After they get lost in the dark, however, Christian realizes that straying from their path was a mistake, and he apologizes to Hopeful, who forgives his companion. The two men turn back, but they cannot get back to the main road before nightfall.
They sleep on what turns out to be the grounds of Giant Despair, who lives in Doubting-Castle. He accuses them of trespassing and throws them into his dungeon. Giant Despair's wife, Diffidence, tells her husband to beat the pilgrims, which he does, and tries to convince them to take their own lives. Christian despairs and contemplates suicide, but Hopeful talks him out of it, convincing him of the sinful nature of that act. Upon finding them alive, the giant beats them again. While Hopeful talks Christian out of suicide once again, the Giant's wife eventually convinces him to kill the pilgrims.
Still in the dungeon on Saturday night, Christian and Hopeful begin to pray. Just before daybreak, Christian realizes he has been a fool: "I have a key in my bosom, called Promise, that will I am persuaded open any lock in Doubting-Castle" (135). It did, in fact, open all the locks, and they escaped back to the main road, which Bunyan refers to here as the King's Highway. Giant Despair hears them leave but his limbs fail and he cannot follow.
To warn others not to make the same mistake they did, the two men erect a pillar with a warning engraved on it. Many future pilgrims were saved by their actions, the narrator tells us, and Hopeful and Christian continue on their way.
The section opens with the life/death opposition that Bunyan frequently employs. Christian has found a new companion in Hopeful, and because Faithful’s martyrdom was the occasion of Hopeful’s conversion, his life (for life before faith is no life at all) has come out of Faithful’s death. Faithful has not died in vain.
The two travel on together, and the first character they encounter is By-ends. Through By-ends, Bunyan critiques the aristocracy. By-ends is wealthy, and though not originally of noble stock, he has married well. His religion, he tells the pilgrims, goes with the “wind and tide,” a metaphor for popular opinion and power (116). Christian and Hopeful quickly move on, having recognized the threat of such a fickle character. By-ends and his friends, whom he encounters shortly thereafter, have studied the Art of Getting, a method of conversion that Bunyan pointedly disapproves of.
Therefore, Bunyan likens By-Ends and his friends, who are well-bred in most standards, to serpents, using the tool of simile. This comparison is an obvious reference to Genesis 1 and the Garden of Eden (118). Bunyan offers his reader a glimpse into these mens' ideology by sharing the conversation they have once they have separated from Hopeful and Christian. By-ends and his mates continue in conversation, attempting to justify their views on religion by misinterpreting scripture (119). Such a mistake would have been a clear signal to Bunyan’s readers, who were well-versed in scripture, that a these aristocrats were professing a false faith. Bunyan indicts them severely a few pages later, “how much more abominable is it to make of him and Religion a Stalking-horse to get and enjoy the World? Nor do we find any other than Heathens, Hypocrites, Devils, Witches, that are of this opinion” (121). These are some of the worst epithets Puritan could levy against another, and with them, Bunyan slams the way the upper class approaches religion. On the following page, he directs his reader to some passages in scripture that bolster his point in yet another strikingly didactic moment.
When Christian and Faithful leave these men, the topography signals the relief and relative ease of their passage while foreshadowing the difficulty to come. They enter a narrow plain called Ease, its width indicating the easy journey they will enjoy for the moment. The next obstacle they face is Demas and his seductive silver mine. If the name of the hill in which the mine is located (Lucre) is not enough to tip off the reader to the nature of this man and his enterprise, his own name certainly drives the point home. Demas is a biblical character of suitably ill-repute. Because he appears in one of Paul’s epistles, we can be sure that Puritan readers would have been familiar with him (see 2 Timothy 4:10). This episode also signals the narrator’s own limit of perception, and that his dreams are not always complete. Bunyan isn’t sure how By-ends and the others come to fall into the pit, but the details of their demise are unimportant. The fact remains that their ill religion met with the justice they deserved.
As Christian and Hopeful continue on their way, Bunyan again conflates time and space. The pilgrims see a pillar that they take to be Lot’s wife, who was transformed into a pillar of salt in the story of Sodom and Gomorrah in Genesis 19. Several things are accomplished when Bunyan invokes scripture in this manner. First of all, it highlights the fact that the pilgrimage should not only be taken literally, as a naturalist progression through space. The pilgrimage is interior and spiritual, and thus draws on a rich Christian vocabulary of images, symbols, and monuments, and the topography is meant to signal a deeper layer of understanding. Second, Bunyan here draws on a knowledge and understanding that he knows his readers already possess. They are definitely familiar with the story of Sodom and Gomorrah, and he assumes the the interpretations and lessons that go along with invoking it in this way. The image of the salt pillar conveys meaning without Bunyan having to expound on it. It is an additional layer of meaning to his own rich imagery that is self-legitimating, and implies that scripture is authoritative.
The next obstacle for Christian and Hopeful, the Giant Despair, is foreshadowed by the thunder and rain, a conventional symbol for danger, as they make their way down the by-path (128). The events at Doubting-Castle do not comprise another social critique, rather, they are a warning to the reader of the temptation of despair. There is a particularly didactic moment in the dungeon in which Hopeful explains to Christian the horror of suicide (132), and though Christian heeds Hopeful’s good advice, he remains upset and afraid. In fact, Christian is so overcome with fear that he becomes it (134). As the Sabbath begins, the two men begin to pray, and as day breaks, they are delivered.
The loaded symbolism of Christian and Hopeful's escape is palpable. They are delivered from the cave-like dungeon on a Sunday, the same day Christ was resurrected. The break of day, and thus the return of the light, is the moment of their deliverance. Like all of Christian’s escapes, this one is divinely occasioned. It is by the grace of God that Christian remembers the key, Promise, hidden within his bosom. The name of the key is significant, for it refers to the Promise of Eternal Life, enacted by God to humanity in the crucifixion. That promise, Bunyan makes clear, is the defense against despair. Per usual, after their escape, Christian and Hopeful memorialize their experience with words, both written on a monument to alert passersby, and sung (135, 137).