This paper discusses a series of commentaries and lyrical texts by Martin Buber and Ludwig Strauss, which dwell on Hölderlin’s poetry and the dialogical ideas implicit therein (e.g. the dialogical vocation of the poet). The paper distinguishes between the dialogical ideal and its concretization in language, as the selected texts all strive to develop a dialogical poetics, yet at the same time engage with textual junctures where the dialogical mode collapses. This collapse is also registered in the historical sphere: Buber’s engagement with Heidegger’s paradigmatic Hölderlin studies calls for a comparison with Strauss’s reception of Hölderlin, and therefore points to an absent dialogue between these two contemporary scholars. This historical lacuna, which Buber may have wished to bridge, thus resonates with ideas on the limits of dialogue in the poetic sphere. The paper draws on further Hölderlin scholars, such as Peter Szondi and Winfried Menninghaus, and their discussion of the lyrical results of failed dialogue, and on the ideas of Franz Rosenzweig and Rabbi Nahman, in the mapping of the dialogical ideas of both Buber and Strauss. Strauss himself thus emerges as a scholar and poet who draws both on Hölderlinian motifs and notions and on dialogical ideas in contemporaneous German-Jewish thought.