In Book 6 Augustine recounts his time in Milan, which was one of profound misery as he struggled in his quest for truth and began to express what he calls a “preference” for the Catholic faith (6.5.7). The book opens with his mother Monica’s arrival in Milan, where she found Augustine “in a dangerous state of depression” following his abandonment of Manichaeism (6.1.1). Augustine describes being in an “emotional crisis” and nearing an “abyss of danger” as he sought Ambrose’s advice, only to find his mentor swarmed by crowds and unable to give Augustine more than a few minutes of his time (6.3.3). Mercifully, Augustine received some solace from friends, especially Alypius and Nebridius, with whom he wrestled over questions of the ultimate good and evil.

Reading this book at the beginning of a new semester and year as I struggle to keep resolutions that are merely weeks old, I am struck by both the privileges and burdens of being a teacher and friend and the ways that we can fall short in both roles.

Augustine’s relationship with his pupil and friend Alypius is especially instructive. Alypius was drawn to Augustine for the latter’s goodness and culture. In turn, Augustine says he was attached to Alypius for his virtue and character, which were apparent even at a young age. Augustine gives an account of Alypius’ tenure as an assessor, in the course of which he courageously refused to be bribed by a senator, leaving everyone “amazed at so exceptional a character who neither wished to have as a friend nor feared to have as his enemy a powerful person, celebrated for his immense reputation, who had innumerable methods of either benefiting or injuring people” (6.10.16). While Alypius showed remarkable fortitude in his dealings with the senator, Augustine divulges his friend was not impervious to temptation, especially when it came to attending circus games by which he was “blinded by an astonishing pleasure” (6.7.12). Augustine notes that during a lecture he capitalized on an opportunity to highlight the folly of these games and inspired Alypius to forsake this bad habit.

If not for his friends, though, Alypius might have avoided acquiring new foibles, but, alas, Alypius’ peers coerced him to attend a gladiator match, physically dragging him there despite fervent protests. Alypius tried in vain to resist watching the spectacle, but he was overpowered by the roar of the crowd. Augustine describes Alypius becoming “inebriated by bloodthirsty pleasure,” returning to the violent contests repeatedly, taking more young friends with him each time (6.8.13).

Admittedly, encouraging one’s friends to abandon their New Year’s diet pledges to share a decadent dessert does not have the same gravity as dragging one’s friend to watch a fight to the death, but Augustine’s description of Alypius’ struggles reminds us of the duty we have to help our friends resist their most arresting temptations rather than provoke them to succumb to harmful habits. However, when the friend is someone over whom we have some fiduciary duty, such as in a mentor and mentee relationship, this responsibility is all the more compelling.

Although Augustine may have helped Alypius break his habit of attending circuses, Augustine confesses that Alypius, who had previously proved unaffected by sexual desire, was so moved by regard for Augustine that he becomes curious about “what it was without which my life, which met with his approval, would have seemed to me not life but torture” (6.12.22). Augustine was so blinded by his own passions that he failed to recognize that he was leading his young friend astray, too. Nevertheless, Augustine relates being anxious to the point of despair that he will not be able to fulfill his obligations to his students amidst the relentless demands on his time, which also left him with no time to contemplate the truth he so desperately sought and the absence of which was the source of the misery that plagued him.

His lament written more than a fifteen centuries ago has particular resonance for a contemporary audience afflicted by the tyranny of the urgent: “‘When can it be sought? Ambrose has not time. There is no time for reading. Where should we look for the books we need? Where and when can we obtain them? From whom can we borrow them? Fixed times must be kept free, hours appointed, for the health of the soul’” (6.11.18).

At the end of Book VI he has a partial response to this question. The first step, he suggests, is seeking knowledge of God, which is aided immeasurably by the company of one’s friends.