linguistic:paraphrasing
Move to Carthage, Rome, and Milan

Augustine taught grammar at Thagaste during 373 and 374. The following year he moved to Carthage to conduct a school of rhetoric and remained there for the next nine years. Disturbed by unruly students in Carthage, he moved to establish a school in Rome, where he believed the best and brightest rhetoricians practised, in 383. However, Augustine was disappointed with the apathetic reception. It was the custom for students to pay their fees to the professor on the last day of the term, and many students attended faithfully all term, and then did not pay.

Manichaean friends introduced him to the prefect of the City of Rome, Symmachus, who had been asked by the imperial court at Milan to provide a rhetoric professor. Augustine won the job and headed north to take his position in Milan in late 384. Thirty years old, he had won the most visible academic position in the Latin world at a time when such posts gave ready access to political careers.

Although Augustine spent ten years as a Manichaean, he was never an initiate or "elect", but an "auditor", the lowest level in this religion's hierarchy. While still at Carthage a disappointing meeting with the Manichaean bishop, Faustus of Mileve, a key exponent of Manichaean theology, started Augustine's scepticism of Manichaeanism. In Rome, he reportedly turned away from Manichaeanism, embracing the scepticism of the New Academy movement. Because of his education, Augustine had great rhetorical prowess and was very knowledgeable of the philosophies behind many faiths. At Milan, his mother's religiosity, Augustine's own studies in Neoplatonism, and his friend Simplicianus all urged him towards Christianity. This was shortly after the Roman emperor Theodosius I declared Christianity to be the only legitimate religion for the Roman Empire on 27 February 380 by the Edict of Thessalonica and then issued a decree of death for all Manichaean monks in 382. Initially, Augustine was not strongly influenced by Christianity and its ideologies, but after coming in contact with Ambrose of Milan, Augustine reevaluated himself and was forever changed.

Augustine arrived in Milan and visited Ambrose, having heard of his reputation as an orator. Like Augustine, Ambrose was a master of rhetoric, but older and more experienced. Soon, their relationship grew, as Augustine wrote, "And I began to love him, of course, not at the first as a teacher of the truth, for I had entirely despaired of finding that in thy Church—but as a friendly man." Augustine was very much influenced by Ambrose, even more than by his own mother and others he admired. In his Confessions, Augustine states, "That man of God received me as a father would, and welcomed my coming as a good bishop should." Ambrose adopted Augustine as a spiritual son after the death of Augustine's father.

Augustine's mother had followed him to Milan and arranged a respectable marriage for him. Although Augustine acquiesced, he had to dismiss his concubine and grieved for having forsaken his lover. He wrote, "My mistress being torn from my side as an impediment to my marriage, my heart, which clave to her, was racked, and wounded, and bleeding." Augustine confessed he had not been a lover of wedlock so much as a slave of lust, so he procured another concubine since he had to wait two years until his fiancée came of age. However, his emotional wound was not healed. It was during this period that he uttered his famously insincere prayer, "Grant me chastity and continence, but not yet."

There is evidence Augustine may have considered this former relationship to be equivalent to marriage. In his Confessions, he admitted the experience eventually produced a decreased sensitivity to pain. Augustine eventually broke off his engagement to his eleven-year-old fiancée but never renewed his relationship with either of his concubines. Alypius of Thagaste steered Augustine away from marriage, saying they could not live a life together in the love of wisdom if he married. Augustine looked back years later on the life at Cassiciacum, a villa outside of Milan where he gathered with his followers, and described it as Christianae vitae otium – the leisure of Christian life.