Song of Riddles is an inquiry into the meaning behind the metaphors that animate the Song of Songs, based on a wide range of source materials and scholarship. The core question prompting this inquiry into the Song of Songs is whether, given the opaque literary confines of the text, it is possible to access the Song's intended subtext, using the text itself as a guide in uncovering its underlying theological message. The nexus between metaphor and meaning in the Song lies at the point at which the three planes of dream-fantasies, riddles, and love wisdom intersect. Understanding how the Song functions simultaneously on these independent trajectories is the first step toward arriving at the concealed meaning of the Song's seemingly impenetrable metaphors.The research presented in this book demonstrates the Song to be part of the rare literary genre of riddles and points to the two lovers in the Song as hinting to the Temple keruvim. These angelic figurines were the sequestered keepers of the Holy Ark and the Divine law, as well as the representatives of the nation of Israel before the Divine presence. The approach to understanding the Song presented in Song of Riddles seamlessly and authentically merges the traditional rabbinic allegorical approach to the Song with the plain sense of the text.