This chapter explores the relation between Schleiermacher's theories and some of the artistic work of his younger contemporary. It focuses on Schubert's settings of two poets: Friedrich Schlegel, a central figure in the Jena circle of early Romantics that flourished at the turn of the nineteenth century, and Friedrich von Hardenberg, usually known by his pen name "Novalis," Schlegel's brilliant soul mate and fellow explorer of ideas. Schleiermacher was the first person to develop a general theory of hermeneutics. In Schleiermacher's terms, Georgiades views Schubert's work as an example of grammatical hermeneutics. In his setting of "Die Berge," one of his 11 settings of texts from Schlegel's poetic cycle Abendrote, Schubert composes out a major-third cycle. In the settings from Schlegel's Abendrote and Novalis's religious poetry, the composer used musical symbols and cross-references to reflect his awareness of that wholeness. Whenever he addressed a poet's work in that unified way, Schubert was practicing psychological hermeneutics.