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Irony theory originated from ancient Greek philosophy, inherited from Socrates’ ironic aphorism, and inspired by the New Criticism and postmodern irony trend. There is no precise definition of irony in Western poetic philosophy, and irony has been subject to controversy in the discourse of literary criticism. Irony is not only a rhetorical style, but also a form of paradox and a poetic discourse. In the early German Romantic era, irony made a leap from rhetoric to aesthetics, and this leap was essentially a revolution of poetic philosophy, in which logic and transcendence reflected each other, and poetics and philosophy were interwoven and fused. We search for the philosophical foundation of romantic irony, explore the double power of irony theory, and ask about the real demands behind ironic words, in order to outline the evolutionary trajectory of F.Schlegel’s thought and theory, so as to discover the theoretical foundation laid by early German Romanticism for the development of European and American literature.