In this article, I will argue that discussing Schlegel’s aesthetic ideas in connection with the themes of mediality and intermediality may disclose an interesting new perspective on his thought, a perspective which also explains the difference between his thought and subjectivism. Schlegel emphasized intersubjective communication instead of withdrawal into the personal sphere of mystical enthusiasm (Schwärmerei). In contrast to mysticism, Schlegel claimed that ironical distance and linguistic mediation were epistemologically indispensable. He understood irony as a dialectical movement that mediates every position and thereby proves the relativity of every viewpoint. According to Schlegel, reaching the level of absolute knowledge was not possible either as a result of conceptual labor or as an immediate feeling. Schlegel tried to mediate the absolute as a result of artistic work and, in that way, reach it as a reward for artistic toil. I will start my discussion with Schlegel’s criticism of the idea of immediacy and explain how he introduced the mediating principle of Romantic irony as the negation of immediacy. Second, I will discuss Walter Benjamin’s 'medium of reflexion' in order to explain why Romantic irony does not collapse into infinite regress. The third section presents Schlegel’s idea of an allegory that refers in a nonconceptual way to the absolute by means of intermediality. I will thereby suggest how one is able to present Schlegel’s aesthetics from a new perspective, if the themes of mediation, intermediality, and aesthetic underdetermination are taken into consideration.