Gregory was born into a wealthy and aristocratic family. He would have been given the formal education of his kind – along the traditional lines of the education of earlier generations of well-born Romans, but by now noticeably somewhat debased even from the standards of Augustine's day. The schools of Rome had received state support in Imperial times, but the war against the Goths had created such disturbance that many of the teachers went elsewhere (to Constantinople or Berytus) and the Emperor Justinian (527–565) had to attract teachers to Rome by paying salaries to professors of grammar, rhetoric, medicine, law. He needed administrators and the emphasis was accordingly put upon achieving competence in the Latin language and a knowledge of the law, rather than the rhetoric with philosophy of Cicero's Rome or the rhetoric with rather less philosophy of Augustine's Carthage and Milan. But academic syllabuses die hard, and there is no reason to think that Gregory got no grounding in rhetoric, or that he learned no philosophy. On the contrary, it is clear that he had a good grasp of both.

The foundation of Roman education had always been the study of Latin grammar. Like Augustine, Gregory seems to have been deficient in Greek, but whereas in Augustine's case that was the result of a lack of aptitude and application, in Gregory's case it is likely that the teaching was simply not available when he was young.