Ancient allures the postmodern social subject trapped in the strangeness of time—the time after the end of history. For that time-beaten subject ancient is the unconscious of coherence, predictability, and certainty. Or perhaps that ancient is a glory fled. Whatsoever, ancient is generally sacralized—irrespective of the type of socialization that happened in the past—and journey to the ancient is often deemed to be a pilgrimage. When ideas of the ancient in their individuality and totality inter alia become the natural intellectual resource for rebuilding postmodern societies, discriminative ingenuity becomes an essential faculty. Any uncritical reverence of the ancient becomes antithetical to modern social and political values, inviting the risk of reproducing inequities of the past. This article problematizes such uncritical dependence on the ancient using Ancient Indian Jurisprudence, which has been looked up on as a repository of moral and legal values, as a case in point. It meditates from the experiences and perspectives of an imaginary ‘teaching subject’ on the many pitfalls and possibilities of the ancient as it builds a framework of teaching and learning, and a representative scheme of evaluation for Ancient Indian Jurisprudence.