In this chapter I first draw from the results of the study of the Byzantine icon to establish the definition of an “iconic mediation” in general. In a second move, I then dissolve the adequation model of mediation, or “seashell model” as inherently iconoclastic. I also outline key assumptions held by the “sonic resonance” model of mediation in Gadamer and the “window” mediation of Marion, concluding neither of them are adequate to account for the mediation of the icon. I thus develop a new schema of mediation, based on the model of a love letter, to guide our understanding of the paradoxical character of iconic mediation which preserves the visceral tension between “everything matters” and “nothing matters.” The love letter, like the icon, can be understood rigorously, but only from a higher point of view, from the horizon of love.