This essay attempts to understand and appreciate what Origen was aiming at in his commentary on the Song of Songs. Origen “imagined” the purpose of reading the Scriptures as the transformation of the reader into the “likeness of God”. He viewed the Song of Songs as the climax of all songs of Scripture and therefore, “learning to sing that song” expressed the highest stage of Christian growth. As the subject matter of the Song of Songs is love, it is clear that perfection in love is indeed the ultimate goal of human life. However, understanding love is difficult and many go astray, because, in fact, as God is love, understanding love and loving is as profound as God Self. It is through the Logos at work in the Scriptures as well as within us and in the whole of the created reality that we are empowered for loving and understanding love. Origen describes the action of the Logos with the image of a “saving wound caused by the arrow of the divine eros”. Origen’s perspective is not that of working towards a fusion of horizons between a human author in the past and a present-day reader, but of working towards an ascent from the level of the “letter” to the level of the “spirit”.