Markan Jesus' radical teaching on divorce and remarriage in the New Testament was considered authentic Jesus' tradition. Jesus' teaching seemed to be hard for the nascent churches to follow literally. In light of this, the composer of the Gospel of Matthew made redactions to the parallel Markan texts, with the noticeable conditional clause, so that it may be applied to the problem of divorce which was inevitable to happen in the church. The principle of Jesus' teaching on divorce and remarriage served as the guideline for the Corinthian Christians, however, Paul made some contextualized interpretations in his teachings to the Corinthians to meet the practical pastoral needs in the changed time and place. This study of the contextual interpretation has the guiding significance to faith and life in the churches today.