This essay investigates the prospect of Romantic Irony’s potential resurgence in contemporary poetics and discusses its relevance and likeness with metamodernism. The internet has by now not only seeped into, but fully permeated, the process of literary production and distribution. The effect of this has been the birth of a new kind of poetic discourse which can broadly be called metamodernism, The New Sincerity or Alt-lit. This movement is characterized by its self-reflexive metacommentary, fragmentary nature and an oscillation between of irony and sincerity. Vermeulen and Akker, among others, have hinted at metamodernism’s relation to Romanticism, but research into the specifics of its tendency towards Romantic Irony is scarce. By viewing the writings of Steve Roggenbuck (a central figure in the new poetic movement), alongside the philosophy of Friedrich Schlegel, I propose a comparative framework for discussion of sincerity, irony and the instrumentalization of contemporary metamodernist writing. I demonstrate that Roggenbuck’s writing displays narratological, tropological and thematic tendencies commonly associated with both Romantic Irony and metamodernism. Apart from broader structural comparison, I attempt a comparative analysis between Roggenbuck’s poetry (2010-2015) and Thomas Carlyle’s novel “Sartor Resartus” (1833-1834) in order to provide a visualisation of the rhetorical and narratological strategies of Romantic Irony. I aim to frame Romantic Irony as a sensibility, or mode of discourse - rather than a strict system of thought - which may still be at work today. In extension, the sensibilities of Romantic Irony may shed further light into the philosophical potential of the seemingly incomprehensible and contradictory tendencies of metamodernism. By ironicizing its poetic form, literary ambition and desire for sincerity in a post-postmodern era, Roggenbuck’s poetry celebrates ambiguity and literary failure, ultimately framing irony as a constructive and potentially democratic operation.