In his account of these early times in Milan, Augustine spends most of his time addressing disparate events and discussions that occurred in his circle of friends and family. One feels he is clearing aside details and setting the scene before launching into an account of his final steps toward conversion in Books VII and VIII. A number of issues are raised and briefly discussed, most importantly those of marriage and the good life.

[VI.1-8] In Milan, Augustine was becoming increasingly open to Christian doctrine, and he begins Book VI by crediting Monica (who has followed him to Milan as well) and Ambrose for this. Monica led a quiet and extremely devout life in Milan, serving as a constant reminder to Augustine that he may well have been destined for Catholicism. Ambrose, as Bishop, was extremely busy and Augustine found it hard to find a moment for a private audience with him.

Ambrose's sermons, however, continued to make an impact on Augustine, particularly in their interpretive approach to the Old Testament. As Ambrose described this interpretive method, "the letter kills, the spirit gives life." A big step came when Augustine learned that most Catholics do not take literally the passage in Genesis in which God makes man "in his own image." He began to suspect that other "knotty" passages in scripture may hide deeper meanings as well.

Augustine was also increasingly attracted to the refusal of the church to offer "proof" of its doctrines. Augustine finds this an engaging form of modesty, and the idea that faith, not reason, is the basis for true knowledge helps alleviate his skepticism to some degree.

[VI.9-24] Turning to events in his daily life at Milan, Augustine recounts some of the issues discussed in his circle of friends. The first concerns a beggar they passed on the way to an important speech Augustine was to deliver. Augustine was miserably nervous about his upcoming performance, but the wretched, filthy beggar appeared to be immensely happy in his drunken stupor. This disturbed Augustine deeply, and he spoke to his friends about "the many sufferings that accompany our follies."

These friends, whose spiritual condition Augustine felt to be "much the same as mine," are named as Nebridius (with whom Augustine had discussed astrology in Book IV) and Alypius, who will later witness Augustine's conversion and become a very close friend. Alypius is described here as full of integrity in his career at the law courts but possessing a potentially "fatal passion for the circus" and public shows in general. Augustine depicts himself and his two friends as three young spiritual questers after truth, and he seems to have depended on their company and moral support.

Having nearly convinced himself that Catholicism is the only place where he will find the truth, Augustine began to worry deeply about the issue of sexual abstinence. Although the church allowed sex in the context of marriage, it encouraged men to try to live without it if possible. Augustine felt at least that he should get married, in large part because marital status and the money that came with the bride (the dowry) would help advance his career to still higher levels. He debated the topic often with Alypius, who had remained chaste after an early and unpleasant sexual experience.

Though fascinated by Augustine's sexual appetite, Alypius argued against a wife, in large part because he and his two compatriots had been toying seriously with the idea of withdrawing from society to lead a bohemian philosopher's life. Nonetheless, Augustine agreed to marry. The bride-to-be was only twelve, however, so the marriage would not have been for a few years. In the meantime, Augustine is forced to send away his concubine (the mother of his son Adeodatus).

Book VI ends with Augustine in a state of extreme suspension, nearly ready to convert, nearly ready to marry, and still plagued by doubts.