The history of confession - or reconciliation as it is often called today - can be divided, roughly, into three main parts: ancient (first through sixth centuries); medieval (seventh through fifteenth centuries); and modern (sixteenth century on). The pattern for confession in the medieval period owes much to the ancient period, so I'll try to do a tour through both.

In the earliest days of Christianity, what we know of confession and reconciliation of penitents was largely carried out according to the suggestions we see in the epistles of the New Testament. Periods of segregation and pentitential acts for sinners before an eventual reconciliation with the community. This process was reserved only for truly serious, scandalous sins that often affected the larger community. For less serious sin, individuals often took on disciplines of fasting, prayer, and almsgiving as ways of repenting.

Over time, the processes of confessing and repenting of sin began to take on an institutional character, were more regularized (at least regionally), and ritual shapes familiar to modern Christians begin to appear. Prayers for God's mercy and praise for God's grace in extending such mercy appear regularly, followed by a confession of sin. The penitent then set about doing righteous and charitable works as a demonstration and expression of their conversion of heart. When this was seen to be sufficient and the church, led by its presbyterate, felt that sufficient prayer for the penitent had been undertaken, they were readmitted to the community in full standing.

In the late ancient period, western Europe began to be influenced by Irish monastics and their ideas about penitence and reconciliation. On the continent, there was a mode of confession that was called "canonical penance". It was a significant event, requiring segregation from the community during the process and it could only be done once in a lifetime. This rule caused many people to put it off until as near to the end of their lives as possible, leading many to die without having completed their penance. This made the practice both difficult and highly unpopular. The Irish monastics offered an alternative, which was focused largely on spiritual direction of the penitent, followed by a conditional absolution contingent on the performance of penance. This pattern gained instant popularity because it was more private that canonical penance and was repeatable. One could be in some stage of repentance and penance all of one's life, if necessary.

There is a bit of overlap in many parts of Europe where canonical penance remains the rule of the church in that region, but the Irish model - sometimes called auricular confession - is the more popular and dominant model. (The Irish monks would take all penitents, even those who were legally bound to undertake canonical penance by their regional laws. Monastics often operate somewhat outside the diocesan legal structures of the church, but that's a different post.)

This is, essentially, the overwhelmingly dominant model in Europe by the High Middle Ages. One confesses privately to a confessor, who is by then a priest or bishop. Spiritual direction and advice are offered and penitential acts are assigned. This portion is where one sees "Thirty Hail Marys and fifteen Our Fathers" in popular media. Acts assigned may be tokens, like these ones, but were also intended to be reparative of damage the sin confessed may have done. So, for example, confession of a theft may involve returning the stolen merchandise or otherwise making whole the victim. An absolution would be pronounced at the end of the confession, but it was understood that the absolution was conditional on the penance being enacted.

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Suggested Sources

Biller, Peter. Handling Sin: Confession in the Middle Ages. York Studies in Medieval Theology, 2. York: York Medieval Press, 2013.

Coffey, David M. The Sacrament of Reconciliation. Lex Orandi Series. Collegeville: Liturgical Press, 2001.

Jennifer Garrison's bibliography of handbooks for confessors.

Edited to add some more secondary sources.