The present dissertation represents a constructive cross-cultural analysis of the philosophical problem of relation (Sanskrit: sambandha). This involves general theoretical questions such as: What does it actually mean for things, or ideas, to be related? Are ‘relations’ real kinds of entities in the world, like a table or my keyboard, or are they merely conceptual constructions; that is, figments of the imagination superimposed on a reality that is essentially non-relational? If the latter, then how do separate, independent things come to be interpreted as things in a relation, i.e., as ‘relata’? In this project, I translate, analyze, and compare texts from three philosophical schools in medieval South Asia that provide distinct answers to these relational questions: (a) the ‘naive realism’ of Nyāya Vaiśeṣika; (b) the ‘eliminativism’ of Pramāṇavāda Buddhism; and (c) the ‘reformed realism’ of the tantric school of Pratyabhijñā Śaivism. Under the hermeneutical auspices of the classical American pragmatists, I employ a characteristically Peircean triadic taxonomy of analysis to bring into clear relief the presuppositions and entailments of these Indian schools in conversation with their 20th century Western counterparts. We come to find that these initially highly abstract relational commitments have far-reaching systematic and practical reverberations, ones that touch upon, among other things: the purported dichotomy between ‘realism’ vs. ‘idealism’; the temporality of causation; the reflexive nature of judgment; the significance of phenomenal continuity; the reality of freedom and value; the active vs. inactive status of the divine; and even the practice of religion and the project of its philosophical reconstruction. By way of conclusion, I gesture towards a constructive philosophical project that I call ‘groundless teleology.’