This paper discusses three dialogues on the possibilities and impossibilities of dialogue. The first of these dialogues is Martin Buber’s dialogue with Indian philosophy. This dialogue is expressed in I and Thou, where he retells a story from the Chāndogya-Upaniṣad and poses a critique of its philosophical message: for him, the here and now is far more significant than the “pure subject,” devoid of objects and objectivity, which the Upaniṣads in his reading aspire to. “What does it help my soul that it can be withdrawn from this world here into unity, when this world itself has of necessity no part in the unity?”  – Buber pleads (1937, 87–89). Buber’s engagement with Indian philosophy finds further expression in a letter he wrote to Mahatma Gandhi in 1939, where he challenges the universality of the latter’s uncompromising principle of nonviolence, in light of the Jewish predicament in Germany and the resistance he envisions against the Nazi regime, which calls for some measure of violence needed – he believed – to eradicate Nazi violence. My second dialogue introduces the writings of Ramchandra Gandhi, Mahatma Gandhi’s grandson and one of the most creative voices of Indian philosophy in the second half of the twentieth century. As a commentator of both the Upaniṣads and the Mahatma, Ramchandra took upon his philosophical shoulders the task of dealing with Buber’s challenge. In his reply to Buber, he touches on the subtle connection between nonviolence and nonduality, injecting new life into the classical Indian notion of Advaita. My third dialogue is about philosophy and the arts, or more precisely, philosophy and painting, through the writings of two thinkers – Ramchandra Gandhi and Ben-Ami Scharfstein – who work at the crossroad of aesthetics, ethics, and politics (postcolonialism). Like Buber, Scharfstein does not merely speak highly of the other, but is willing to make the effort to meet him or her across numerous boundaries, inner and outer. Like Ramchandra, his work in the field of aesthetics goes beyond the aesthetic and aims to underscore cruelty, exploitation, and general blindness and deafness to the other all around us, and hopefully to contribute to the establishment of solidarity in place of bifurcation and partition. The discussion of solidarity, or alas its absence, and the violent consequences of this absence, is extremely relevant to the current situation in Israel, where dialogue seems (almost) impossible and solidarity – across chasms and differences – sounds like a foreign word.