This paper correlates Sigmund Freud and Rabindranath Tagore's writings on mourning through two specific texts. Despite being contemporaries and profoundly influential, Tagore and Freud's spheres of influence have tended to be separate, so that there have been but few attempts at connecting their philosophies. This essay examines the second chapter of Tagore's novella Play of Four (Chaturanga, 1916) in the light of Freud's essay ‘Mourning and melancholia’ (1917). It explores how mourning may at once demand confirmation and denial; how it affects love and desire. The essay examines the Freudian concept of the unconscious through Tagore's symbolism; it also looks at Tagore and Freud's references to autobiographical elements and Shakespeare in their writing. The paper thus offers a close and juxtaposed reading of texts by two of the most important writers of the past century, who wrote and revolutionized our thinking about human minds and lives. In doing so, it throws new light on Tagore's novella and further proves the universality of Freud's propositions.