The aim of this essay is to carry forward this author’s dialogic encounter with Daya Krishna, drawing not just on his well-known essays but also on his unpublished papers and private correspondence, in an attempt to think dialogically about the very notion of dialogue or, in Sanskrit, saṃvāda. This is perhaps the key notion in Krishna’s “project” of reading and thinking old texts and philosophical strands anew. Further touched on here is the question of newness in philosophical thinking, and the interlacement of newness and creativity. Here the dialogue is broadened to include K. C. Bhattacharyya, Mukund Lath, and Arindam Chakrabarti, each of whom works with the newness/creativity question and connects to Daya Krishna in his own way. In our dialogical journey we stop at the central and well-connected ‘stations’ of language, knowledge, and freedom. Krishna’s uniquely self-conscious use of language is discussed. His intriguing notion of knowledge-without-certainty based on dialogue-as-pramāṇa and his emphasis on what he saw as the inseparability of knowledge and action are spotlighted. Finally, Krishna’s critique of classic formulas of freedom-as-disengagement (e.g., in Patañjali’s Yogasūtra) is discussed. He himself envisioned an alternative notion of freedom as a voluntary two-way movement between withdrawal and return, retreat and re-engagement. In this respect he demands enlightened action, aiming at the transformation of the down-and-out, inspired by one’s visit, or repeated visits to the above and beyond.