Since Faithful perished, his testimony brought forth a new believer, Hopeful, who asks to go along with Christian to the Celestial City, and on their journey they meet up with ByEnds who admits to only being interested in religion when it “goes about wearing silver slippers” and never strives “against the wind and tide.” Christian and Hopeful keep their distance from him until ByEnds joins up with three men, Mr. Holdtheworld, Mr. Moneylove, and Mr. Saveall, who justify using religion only for profit while mocking Christian and Hopeful for being too judgmental; later all four men approach Christian and Hopeful with the intent to assail them, but Christian uses Scripture rightly forcing them into speechlessness. Leaving the four men, the two pilgrims pass Demas who tries to persuade them off track, to no avail, as there is a reminder of what happens when one even desires in his heart of another way: Lot’s Wife who stands as a pillar of salt for just looking back in the Way.
The path was rough going until Christian notices a path that travels next to the Way, and though Hopeful is apprehensive that it would not take them to the Celestial Gate, they climb over the fence to the other side; suddenly it begins to pour as the path becomes flooded, and the pilgrims find shelter under an overhang. Unfortunately they are on the property of Giant Despair, and he throws them into a dungeon for several nights without food, water, or light; he also beats them and suggests that they should decide their fate: a knife, a noose, or poison. Christian no longer wants to suffer, but Hopeful encourages him to persevere, and soon after Christian remembers his Key of Promise which allows them to escape from the Giant and their prison.