Idealized religious worlds often have the effect of drawing peoples' attentions away from the present reality and instead towards a superior, divine reality. For this reason, American philosopher George Santayana calls for a metaphorical interpretation of religion, akin to the metaphorical interpretations of reality as found in poetry. My thesis explores the role of play (or līlā) in religious practices and how these sacred practices have potential to carry over into the mundane world. Essentially līlā translates as "play" or "sport" and in Hindu Gauḍīya Vaiṣṇava tradition it can refer to the play of Kṛṣṇa in the land of Vraja or it can refer to the theory that the cosmos were created and maintained for the sole purpose of play. Devotees try to find union with Kṛṣṇa by entering into his līlā through the act of play. In practice, these methods of playing may not just be confined to a separate, sacred space, but could be incorporated into one's way of being in the world at large. With this in mind I will examine the līlā practices of rāgānugā bhakti sādhana, rās līlā, and the Ban-Yatra pilgrimage through the lens of Santayana's theories to determine to what extent each practice integrates the spirit of play with the world as a whole.