This dialogue explores the question of whether intentionality––the “ofness”, “aboutness”, or “directedness” of mental states––is a relation. We explore three views: the Naive View, on which intentionality is a relation to ordinary, everyday objects, facts, and other such items; the Abstract Contents View, on which intentionality is a relation to mind-independent abstract entities; and the Aspect View, on which intentionality is a matter of having intentional states with particular (non-relational) aspects that are our contents. We consider the challenges facing these views, which include empirical challenges in accounting for all the contents our intentional states can represent, metaphysical challenges in making sense of how contents can be entertained or otherwise represented by us and how they can play a psychological role in the mental economy, and challenges in making sense of how intentionality connects us to the world––if at all. Along the way, we consider the question of how consciousness is related to intentionality and how this affects one’s choice of views.