Belonging genuinely to ourselves and others, sharing voices in building community and destiny makes us human, historical beings. Our basic attunement not to a general or current ideology or habitual ways of speaking and thinking, but to the unrecognizable, unspoken dimension of words seems to determine essentially our experience of being at home in the world and our vocation as well. Yet, how are we to find an originary place of life-opening that makes human co-journeying on earth possible? Do we discern in the given intellectual and spiritual heritage any sign (Wink) aiding our building a homely abode for historical man? This paper re-collects Hölderlin’s work: his meditations on human relations to the Wesen of language and the question of destiny through his translations of Sophocles, his conception of tragic agon and of caesura, his personal letters and three poems to shed light on Hölderlin’s extraordinary tragic and poetic vision. Reading “The Ister” will involve a textual dialogue with Heidegger’s elucidation of the poem and trace the shared traits, between the poet and the thinker, signs of a different future and of the unconditional, destinal historicalism of language and Being (Wesen) which remains beyond anyone’s possession. Attending to Hölderlin’s struggles with the poet’s vocation and responsibility, will also, albeit indirectly, question those of Heidegger the thinker in his 1933–34 allegiance to Nazism and his long silence afterward.