After discussing different phenomenological modes of presence, I argue that the full force of the icon’s visual language is meant to bring us into an encounter with the listening presence of a person. This begins to emerge through the painting’s natural aesthetic presence as a portrait, but can only come to full fruition for the one who prays. After a phenomenological account of the act of prayer, I show how the experience of the icon takes on a critical structural difference for those who come before the icon in the conviction that the words that they say and actions that they perform are truly communicated to the person who is visibly present.