Jerome trained in Rome under the grammarian Aelius Donatus, mastering classical Latin rhetoric so thoroughly that he later described a dream in which he stood before a divine tribunal and was condemned as a Ciceronian rather than a Christian, more devoted to pagan style than to scripture, a vision he said left him unable to touch a classical text for years afterward. Around 375 he withdrew to the Syrian desert near Chalcis to live as a hermit among a small community of ascetics, a period he later described as one of fierce temptation, in which he imagined the dancing girls of Rome even as he fasted among scorpions and wild beasts.
It was in this same desert period that Jerome began learning Hebrew from a Jewish convert to Christianity, a highly unusual step for a Latin Christian scholar of his time, when most Western theologians worked entirely from Greek or from Old Latin translations already once or twice removed from the Hebrew original. He called the study bitter and difficult after the ease of Ciceronian Latin, but it gave him a qualification almost no other Latin Christian writer of his age possessed, direct access to the Hebrew Bible rather than dependence on the Greek Septuagint translation that earlier Latin versions had been made from.
After periods in Antioch, Constantinople, and Rome, where he served briefly as secretary to Pope Damasus I and gathered a following of aristocratic Roman women devoted to ascetic study of scripture, Jerome settled permanently in Bethlehem in 386, founding a monastery beside the traditional site of Christ's birth where he would spend the rest of his life.