This chapter identifies a strain of political, affective maladjustment it labels “Hopeless Romanticism,” of which Percy Bysshe Shelley is an exemplary case. It argues that hope plays a fundamental role in the progressivist refusal to abide by the terms of the status quo. Hopeless romantics hold on to visions of a better world in spite of the crushing realities that surround them. This chapter tracks how this affective mechanism manifests in a series of Shelleyan poems where hope leaps past probabilistic boundaries, even as the despair that is hope’s other side repeatedly intrudes. Hope’s structural investment in futurity has made it both a symptom of weakened individual agency and a social portent of political change.