Now 30, Augustine is dismayed by his own indecision. He is still ambitious for worldly success, and he cannot imagine giving up sex for a life of religious celibacy. Monica arranges for him to marry a Christian girl from a good family, but she is too young, so the marriage is postponed two years. Augustine and his friends talk about withdrawing from the world to take up a life of philosophical contemplation, but the plan falls apart when they realize their wives will not approve. Augustine sends away his concubine in preparation for the marriage, and her loss causes him great pain. But he cannot bear the thought of two years without sex, so he finds another woman. His only solace is the conversation of his friends, and friendship forms the one pure bond in his life.
The latter half of Book 6 opens with a marvelously ironic summary of the events leading up to Augustine's current situation and his mental state at that point in life. Augustine speaks in a kind of internal monologue, restlessly hopping from one source of enlightenment to the next — Faustus, the Academics, Ambrose — and constantly asking anxious questions that never quite get answered: "How will I find the right books to give me the answers I want, and even if I ever find them, when will I get time to read them?" The tone is one of self-mockery, and it contributes to the oddly comic feel of Book 6. A further comic touch occurs later in this section: Augustine's group hatches a high-minded plan to withdraw from the world and do nothing but contemplate philosophical questions, but the idea instantly collapses when the real world interrupts: Their wives will never let them do it!
Worldly concerns are pressing hard on Augustine. Always fond of triads, Augustine identifies his three worldly temptations: honors, money, and marriage. He has already established a highly successful career: He has secured a plum government position, won prizes for his orations, delivered tributes for the emperor, and attracted the attention of powerful men. He and his friends are doing so well, in fact, that they are beginning to contemplate how they can become the governors of minor provinces, not an impossibility provided that they can prevail on their network of influential friends and they can marry into enough money.
Marrying into money appears to be exactly what Monica arranges for him. As Augustine presents it, Monica's motivations are relatively pure: She wants to see him legitimately married into a good Catholic family, hoping that he will then be baptized. However, the fact that Monica has followed Augustine to Milan — most likely with at least one of his brothers (Navigius, who appears later in the narrative) and possibly two cousins — seems to indicate exactly how much the entire family has pinned its hopes on Augustine's success and social status. The marriage Monica contracts for Augustine is purely a social arrangement, not a love match. The girl herself is two years below the legal age for marriage, which makes her 10 years old, while Augustine is 30, but the wide difference in age was common in contracted marriages. Dreams again play a role: Monica has dreams and visions about the marriage, but she knows that this time they are false, generated by her own desires rather than by genuine communication from God. Nonetheless, she continues with the plan.
One consequence is that Augustine's concubine has to be disposed of. She is sent back home to Africa, although their son, Adeodatus, stays with Augustine. Many writers have pointed out that despite the pathos of the scene, it is a reflection of the social realities of the time. No one in Augustine's social circles would have considered his concubine marriageable. Concubinage was a legal gray area, one made necessary by the rigid class system of late Roman society, in which marriage was an alliance between families and estates, not an affair based on personal preferences. It was inevitable that at some point, Augustine, the successful rhetor, would be expected to contract a legally sanctioned marriage with a bride from a respectable family. These facts are important to understanding Augustine's world. However, they do not adequately account for the way that Augustine reports on the event. Augustine describes it without sugarcoating the facts or attempting to excuse his behavior. He makes quite clear that he is abandoning his partner in a faithful relationship of 15 years, the mother of his son, strictly because she has become an obstacle to his success. Throughout the passage, Augustine is careful to put all the blame on his side. His mistress, in fact, comes away with the moral high ground, because she vows to live a life of religious celibacy, something Augustine acknowledges he could not do. Augustine's behavior grows worse: Although he grieves for the loss of his concubine, he cannot imagine going without sex for two years, so he takes another lover for the interim. The event is reported as yet another of Augustine's blame-worthy actions, the product of his ambition, his concupiscence, and his willing involvement in the hollow values of his society.
The immediate contrast to the repudiation of his concubine is Augustine's devotion to his friends, the one pure and blameless aspect of his life. He acknowledges that he could not recognize it at the time, but he could never have been happy without the companionship of his friends, who were still accompanying him on his painful search for truth. This pure friendship is the opposite of the selfish physical lust that mars Augustine's relationships with his concubine and his temporary lover.
Epicurus c. 341-270 B.C. Greek philosopher who held that the ultimate good was to feel pleasure and avoid pain. Epicurus made a famous argument concerning God and evil, to which Augustine may be alluding: "Is God willing to prevent evil, but not able? Then he is not omnipotent. Is he able, but not willing? Then he is malevolent. Is he both able and willing? Then where does evil come from? Is he neither able nor willing? Then why call him God?"