The advent of modern hermeneutics is inextricably bound up with German romanticism. This chapter charts the emergence of modern hermeneutics by identifying and detailing philosophically three phases of its development in romanticism. First, there is discussion of the hermeneutics of the Jena circle of romantics, where focus falls on Friedrich Schlegel – in particular his account of philosophical irony, fragmentary philosophical expression, and the absolute. The treatment connects these central philosophical conceptions to Schlegel’s philosophy of language and historiography. Interpretative understanding is a general mode of experience for Schlegel, significantly broadening the scope of hermeneutics from its home base in textual exegesis. In the second phase, romanticism provides hermeneutics with its earliest modern systematic form. Here the narrative turns to Schleiermacher’s systematization of hermeneutics – to hermeneutical theory correctly so-called – as contained in his Berlin lectures. Last, hermeneutical theory is extended scientifically by the work in the philosophy of language and comparative linguistics of Wilhelm von Humboldt. Taken together, these three phases of the interaction of hermeneutics and German romanticism constitute the core European understanding of hermeneutics prior to its reconceptualization in phenomenology.