In the year 371 at the age of seventeen years Augustine left home in Tagaste once again to study at Carthage. He also he entered into a stable relationship with a woman whom he came to love dearly but whose name we do not know. In the year 372, his unnamed concubine bore him a son, Adeodatus, which in Latin means "given by God." They lived in Carthage until the year 374, when they returned to Thagaste, the place of birth of Augustine.

There he began a small school that taught grammar. They moved back to Carthage in 376, where Augustine now felt confident enough to open a more formal school of rhetoric. He persisted there for eight years, while Adeodatus approached adolescence. In 383 the young family moved to Rome, to be reunited with some North African friends, including Alypius, Augustine's life-long friend. In 384 they moved to Milan. Monica joined them in Milan in 385. She arranged for Augustine a marriage to a woman of an appropriate social class. Augustine reluctantly accepted the plan as a means to advance his career. For Augustine, this meant he had to send away his faithful partner of fourteen years, who was the mother of Adeodatus. 

This separation was emotionally wrenching for both of them. The woman went back to North Africa, and Adeodatus remained in Milan with his father and with Monica, his grandmother. Adeodatus was therefore in Milan at the time of the conversion of Augustine in 386. Indeed, father and son prepared for baptism together, and were baptised, along with Alypius, at Easter 387 by the Bishop of Milan, Saint Ambrose. In 387 Adeodatus was present with Augustine and Monica at the port town of Ostia, await a ship back to North Africa. He witnessed his grandmother's death. Augustine wrote that Adeodatus had to be consoled afterwards. The journey back to North Africa was postponed, and father and son then spent over a year in Rome.

Adeodatus accompanied Augustine back to Thagsate, where Augustine sold the family property and began a lay Christian community. The early writings of Augustine from this period covered his dialogues with his son. As a proud parent Augustine wrote that Adeodatus was intellectually advanced for person of only seventeen years of age. In the year 390 Adeodatus died before reaching his eighteenth birthday. He had been the object of the tender solitude of his father. Within a period of three years, Augustine had lost both his beloved mother and his son through death. Augustine always fondly remembered his son, who he believed surpassed many educated persons: “The brilliance he evinced filled me with awe,” and added, “I remember him without anxiety, I have nothing to fear about anything in his boyhood or adolescence; indeed I fear nothing whatever for him.” [Confessions 9,6,14]

Augustine the parent, even in the evening of his life expressed poignant regrets for the unachieved promise that was cut short by the early death of Adeodatus. Augustine’s thoughts of the child he admired, grievously present in his absence, like a lost limb, is revealed by a sentence in his last book, where Cicero speaks for him: ‘Do not these words of Cicero for his son come from the viscera of every father, when he says to him in a letter: “Of all people, you are the only one I would wish to surpass me in everything.”

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