Scripture scolds Will for not understanding her teachings. Will begins to cry and falls asleep, slipping into another dream. In his dream, Will is captured by a woman named Fortune and taken to the “land of longing and love.” Fortune’s maids are called Concupiscentia-Carnis and Covetousness-of-Eyes. Both ladies entice Will, telling him that he is at the peak of health and can have a life of lust and pleasure.
Will’s inability to grasp Scripture’s teachings points to how difficult it is to fully understand the Bible—especially for an everyday Medieval man like Will. It also suggests the need for the clergy to provide this understanding to the third estate (and for the clergy to therefore not be corrupt when providing such instruction).The dream-within-a-dream that Will experiences further underscores that he is an imperfect, everyday human, swayed by the promise of Fortune (especially tempting due to Will’s poverty).
A man named Old Age warns Will to be cautious, as Fortune and her maids and will fail him during his “greatest need.” A man named Recklessness, dressed in “ragged clothes,” tells Will not to listen to Old Age and claims that Fortune and her companions “will not grieve you greatly, nor, unless you wish, beguile you.” Much to Old Age’s dismay, Will is pursued by Covetousness-of-Eyes for so long that he no longer “give[s] a damn for Do-Well and Do-Better.” Covetousness-of-Eyes convinces Will that as long as Fortune is on his side, friars will love him.
Old Age has the wisdom and experiential knowledge that Will lacks, so he is able to discern that Fortune is ultimately unreliable. Covetousness-of-Eyes draws a connection between Fortune and friars, once again revealing the corruption in the Church. Instead of serving and instructing the sick and the poor, friars are selfishly drawn to those who have money and power.
Will’s golden years come to an end, and he grows old and impoverished. Fortune abandons him, suddenly an enemy rather than a friend. The friars also turn away from Will since he asks to be buried at his home parish where he was baptized, rather than on the friars’ land. Angry, Will asks the friars why they care where he’s buried, saying, “you couldn’t possibly care less / Whose earth covered my corpse once you’d acquired my silver.” He accuses the friars of caring more about confession and burial than baptizing converts. Will asserts that baptism is most important, since “without baptism a baby may not be saved.”
As Will ages, he gains some of the experiential knowledge (“natural knowledge”) he’s been lacking. He’s able to recognize that the friars’ priorities are misaligned, as they’re preoccupied by confession (which could lead to financial gain) and who is buried at their brotherhood. Will’s pedagogical moment—when he teaches the friars of the importance of baptism for salvation—also shows Will’s spiritual growth.
Will longs to tell other people about his dream. A man named Lewte appears and tells Will, “Thou shalt not hate the brothers secretly in thy heart, but rebuke them publicly.” Will argues that if he rebuked the friars publicly in his waking life, the friars would also use scripture against him, quoting “Do not judge any one.” Lewte tells Will that the point of law is to bring corruption to light, for “What the whole world’s aware of, why should you hesitate / To write about it in a book to rebuke deadly sin?”
Lewte represents justice, although the Medieval conception of justice centered on relationships and was more like today’s understanding of loyalty. Will’s prediction that the friars will defend themselves by using scripture selectively refers back to the friars in the “field full of folk” who distorted scriptures to make themselves look good.
Scripture reappears and agrees with Lewte before shifting the conversation to talk about faith. Scripture claims that people are only saved by faith in Jesus, but Roman Emperor Trajan appears and objects to Scripture’s conception of salvation. Trajan explains that he was an “unchristian creature” and was thus damned, but because he lived his life with love and upright moral character, Saint Gregory the Great intervened and Trajan was saved from Hell. Will thinks about how Trajan was saved “Not through prayer of a pope,” but through “lawful love and living in truth.”
In the Middle Ages, there was great concern about what would happen to non-Christians who lived moral, loving lives. The story of Trajan, a non-Christian Roman Emperor who was famous for his commitment to justice, began to circulate as an answer to this question. Saint Gregory the Great’s intervention, and Trajan’s subsequent rescue from Hell, shows that God’s mercy may save morally upright non-Christians.
Trajan explains that “Law without love” is worthless, as are all crafts that are not learned out of love for God and other people. Continuing on the topic of love, Trajan teaches Will, “For whoever hates us it’s our merit to love.” He explains that it is also a Christian’s duty to love the poor unconditionally and take care of them. He affirms, “we should be lowly and loving, and loyal to each other. / And patient like pilgrims, for pilgrims are we all.” Trajan also points out that poverty is a good thing, because it makes a person less fearful of death and less distracted by material possessions. He thinks priests would be better off not accepting silver for their services.
Trajan’s teachings encompass several key themes in the poem: the central role of love in the Christian life, the concept of doing good works out of love for God and other people, and the way that working hard can lead to salvation. Trajan’s criticism of amassing riches echoes Scripture’s earlier teaching but is more pointed in that it directly criticizes the priesthood.
Still dreaming, Will sees Kind, who calls him by name. Will is “lifted aloft” and sees a variety of scenes from nature, from “wild worms in woods” to “how men took Meed and dismissed Mercy.” Will notices that Reason “respect[s] and rule[s] all beasts,” but doesn’t seem to intervene with humans. When Will pointedly asks Reason why he doesn’t guide mankind, Reason tells Will to mind his own business. Reason warns Will, “before you belittle my life see that your life merits praise.”
Kind, one of the two representations of God, appears briefly to have Will learn from nature, which consequently teaches him about what has gone wrong among humans. This passage is reminiscent of T.H. White’s The Once and Future King, when Wart (young King Arthur) learns from an array of different animals with help from his mentor, Merlyn.
Awakening from one dream but still deep in another, Will finds himself face-to-face with a man named Imaginative. Imaginative scolds Will for being rude to Reason, asserting that Will “Praised and dispraised things of which you were not a proper judge.”
Imaginative doesn’t represent the modern-day conception of imagination. Instead, he represents the human mind’s ability to form mental pictures to aid in memory or visualization. Imaginative’s comment that Will shouldn’t be judgmental suggests that Will is still spiritually naïve and prideful.