Theories of historical and political change often rely on the idea of a breaking point at which radical action becomes a necessity. Theories of impasse—whether historical, political, or linguistic in focus—respond more or less directly to the assumptions behind this idea. This essay queries these assumptions. Opening with a discussion of how the concept of “the intolerable” features in the work of radical thinkers, the first section examines Lauren Berlant’s project in Cruel Optimism and explores her notion of “the impasse of the present.” The second section then turns to the work of Paul de Man, who, from Allegories of Reading on, develops a complementary theory of the impasse of the present that grows out of his theory of rhetorical reading. Although Berlant and de Man are each preoccupied in different ways with the idea of impasse, both ultimately demonstrate that impasse is best understood as an impossibility. Through readings of KC Green’s webcomics “On Fire” (best known as the source text of the “This is Fine” meme) and “This is Not Fine,” the essay illustrates and considers the broader implications of this impossibility.