This article looks into the phenomena of irony and hope as well as their relation. The article starts out with an analysis of Richard Rorty’s understanding of private irony and social hope. Here, I argue the case that Rortarian irony is not primarily a matter of epistemic skepticism but instead an existential stance meant to deal appropriately with the idiosyncratic nature of one’s private projects. Moving on, the article focuses on Jonathan Lear’s depiction of two peculiar instances of two phenomena: radical hope and ironic disruption. Whereas radical hope is the experience of hope in a crisis situation where all meaning—and thus every reason to act—has been lost, the experience of ironic disruption accentuates the constitutive instability and openness of the practical identities we inhabit. Insofar as Rorty cannot account for these phenomena, Lear’s analyses present a serious challenge to Rorty’s neo-pragmatic philosophy.