This paper seeks to explore the academic approach to interreligious dialogue by outlining some key features of what the author sees as its philosophical foundation: understanding. It argues that understanding what it is to understand is crucial to developing interreligious dialogue because, at its core, the goal of such dialogue is the exchange of differing religious understandings for mutual benefit. Thus, the author contends that a thorough academic perspective on interreligious dialogue can only be established if a robust account of understanding is first constructed. Having addressed this, the author outlines three key features of understanding: subjectivity, internality, and appreciation of the whole. Following this, a curious aspect of the generation of new understanding is explored, namely the seeming link between leisure, the absence of so-called “servile” work, and the generation of new insights. Whilst this collection of key features is by no means exhaustive, this paper seeks only to open a conversation on the nature of understanding that has been noticeably absent from philosophical and theological discussion in recent years. Given this, the author hopes to open avenues through which others might critique, explore, or add to the features identified in this article in order to expand the neglected field of the Philosophy of Understanding.