Monica followed Augustine to Milan by sea, but before embarking she had another vision during which she learned that she would arrive safely. She encouraged the sailors on board, who were usually the ones to assuage the fears of the passengers rather than be comforted themselves. In Milan she led a quiet and devout life that inspired admiration in Augustine and made him wonder whether God had predestined him to be a Christian after all.
While in Milan, Monica followed the African custom of bringing baskets of bread and wine to honor the dead saints. Small meals were taken at the shrines of these saints, and sometimes led to drunkenness on the part of those who attended. Monica's offerings never inspired such debauchery, but she was nonetheless told to put an end to them by Bishop Ambrose. Augustine admired Monica's unquestioning acceptance of Ambrose's authority.
Augustine still struggled with the idea of "spiritual substance" - how, he wondered, could God be spiritual but still have created man in his own image? He learned that most Christians do not take this passage in Genesis literally, but rather have learned to gain figurative truth from the Bible in instances of philosophical and theological difficulty. Ambrose quotes Corinthians to his congregation: "The letter kills, the spirit gives life" (2 Cor 3:6). In other words, it is not always proper to read the Bible literally. Ambrose believed in figurative exegesis, which alluded to deeper truths than what appeared to be on the surface. Augustine also suggests that it is the contradictory passages in the Bible that may offer the most profound insights. He has come to believe in the great authority of the Bible, and is thus willing to read it spiritually and figuratively, rather than with logical skepticism.
The Catholic Church in Milan refused to provide philosophical proofs for all of its doctrines, as many "heretical" sects and cults were doing at the time. Refusing to associate themselves with the fashionable philosophies and fad religions of the day, the Christians removed themselves from these philosophical debates and returned to the idea of internal faith. While in Milan, Augustine came to admire this practice, and rather than attacking it as cowardice or error he saw it as a kind of institutional modesty.
During this period, Augustine was spending a great deal of time with two friends from Africa who had also come to Milan, Alypius and Nebridius. They were young seekers of truth, and often discussed the best way to find it. They bandied the idea about of withdrawing from the city and living a contemplative, bohemian life. One day, on the way to deliver a panegyric on the emperor, Augustine and his friends passed a drunken beggar. While Augustine was miserably nervous, the three discussed how this worldly ambition is folly and causes suffering. Augustine laments how he was obliged by this ambition to "drag the burden of my unhappiness with me."
Augustine writes that he had now come to the brink of conversion and had begun to concern himself with the practice of a righteous life in regards to sexual matters. His friend Alypius had been abstinent since an unfortunate encounter in his youth. The two discussed what might be done, and Augustine became certain that he must marry. The Church at that time allowed sexual contact within marriage, but encouraged all its members to live without it if they could.
Marriage also promised a rise in station and fortune for Augustine. From a financial and political standpoint, it was necessary for a man who had ambitions in public life to marry well. There was no consideration in this matter of personal feelings, except with regards to the suitability of the partnership. Through the efforts of Monica, a girl of ten was chosen as "suitable" (under Roman law it was necessary for the girl to be at least twelve years of age). Augustine writes that the girl "pleased" him, and it was decided that they would be married when she came of age. Augustine holds that Monica was motivated by her Christian faith, rather than by any aspirations to political or financial gain.
Adeodatus and his mother (Augustine's "companion" for many years) accompanied Augustine to Milan. The woman soon proved to be a hindrance and returned to Africa, leaving Adeodatus in Augustine's care and vowing to never be with another man. Augustine says that "My heart which was deeply attached was cut and wounded and left a trail of blood." Though Augustine claims he was saddened by her departure, he quickly procured another woman to be his concubine, as he was not able to marry for another two years. He sorrowfully confesses to his shameful addiction to lust.
Augustine ends Book VI lamenting his own weakness and error. He discussed his problems with his friends Alypius and Nebridius, and they critiqued the materialist philosophy of Epicurus. He could not understand why material things were not giving him perfect happiness, and why he was continually sorrowing. He was confused about the "proper" way to attain and enjoy beauty, and concerned that he could not see beauty with his inner eye. However, he loved his friends for their own sake, not for the pleasure they gave him, and he hoped that his awareness signaled the beginning of his enlightenment.
The remarkable way that Augustine uses the progress of his own life to illustrate the way of the soul toward God is now coming almost to the point of conversion. By relating his own follies and sins, he shows how the soul and the mind, once partially convinced of the truth of the faith, still cling to the vain pleasures they care for the most. Augustine details his many stumbling blocks on his path to Jesus, and notes that a major obstacle was his sexual appetite. He kept his concubine with him from Thagaste, to Carthage, to Rome, and to Milan, and when she was finally sent away he quickly procured another.
Augustine's coldness in the matter of the dismissal of the mother of his son is tempered by his avowal that his heart "bled" for her, but he did not prevent her from leaving. Perhaps Monica can be blamed for Augustine's casual attitude toward the departure of someone who had become family. The Roman custom of marriage was not particularly romantic; it was, in most cases, a business proposition. In Augustine's time there were few illusions about people's sexual appetites and very little sentimentality surrounding personal relationships. Most people, including the Christians with whom Augustine was beginning to consort, would have applauded his repudiation of his companion and his proposal of marriage to a ten-year-old.
While such conduct is shocking to our modern sensibilities (and hardly the kind of behavior we would expect of a saint) we must consider it in the context of Augustine's day, when these were accepted behaviors. However, as Augustine is quick to point it out, his behavior in these matters was reprehensible. Perhaps he chides himself for slightly different reasons than we would (he finds fault with his attachment to sex in general, whereas the modern moralist would take issue with Augustine's willingness to wed a child), but he is not sparing in his criticism of himself.
Monica's arrival in Milan seems to seal Augustine's decision to become a Christian. The world of the late Roman Empire was one of such depravity and violence (the circuses to which Augustine's friend Alypius was addicted, for example, were horrifically bloody affairs) that the Church may have seemed the only sane institution in an insane world. Augustine takes care to explain to us his very personal (but rather extraordinary) search for the truth, and is meticulous in recounting the psychological processes he went through during this search.
The extreme youth of Augustine's bride-to-be was a common occurrence. As there were virtually no opportunities for women within the Roman world, twelve-year-olds girls regularly married older men. They could even marry before the age of twelve and live with their parents until they were considered old enough to live with their husbands. In earlier years, Roman custom held that women in patrician families should wait until their eighteenth - or at the very least, sixteenth - birthday to wed, but by the late Roman Empire these standards had become lax. The girl, whose name we are never told, would have been from the same - or perhaps a slightly higher - class as Augustine. She would have been chosen in an agreement between Monica and her parents, and would have had no say in the matter.
Critics of Augustine point out that he should have kept his faithful companion with him, but doing so would have been an impediment to his baptism. The social conventions of his day prevented him from marrying his companion because of the differences in their class. The woman he sent back to Africa could never have expected to marry Augustine; likewise, his wife-to-be would probably not have expected Augustine's heart to "bleed" for her, as she was chosen for suitability rather than for love or sexual attraction. Augustine's society was far more concerned with property and status than with personal feelings. This was the world Augustine lived in, and his actions are not surprising when considered in the context of its dictates.