This article argues that from classical to early modern times, repentance and forgiveness have been experienced as desired qualities for human coexistence in a fallible world. The early church Fathers reveal a basic continuity in expression of repentance between Christianity and the classical world, as the church sometimes resorted to prevailing cultural mechanisms for reconciliation. These included a common evaluation of the past and the public commitment to a different way of life. Christianity emphasised the vertical dimension of repentance, as it insisted on God as an involved party who was transgressed against by any form of horizontal human sin. This went far beyond the occasional provocation of individual gods by arrogance but was personal and relational in character. The church integrated the practice of repentance and conversion through special days and seasons, as well as by an emphasis on the Holy Scriptures as the divine standard for human living. Although formats differed, the theological notions show a spiritual agreement and consistency. For repentance to qualify for forgiveness, a baptised Christian required conviction of sin, reconciliation through God’s appointed means, and a proven new course of behaviour that complied with divine standards.