In this chapter, we argue that a distinct concept of “aesthetic hope” emerges from the way Kierkegaard’s Aesthete treats hope [Haab] and its relationship to recollection [Erindring] in “The Unhappiest One” and “Rotation of Crops.” We first show that aesthetic hope is distinct from the two other kinds of hope discussed by Kierkegaard: temporal hope and eternal hope. We then consider the suggestion that aesthetic hope is also an expression of despair – an inverse hope against hope, which seeks to avoid disappointment by hoping for things that are in some sense certain. The aesthete’s recommendation that we hope in such a way illuminates Kierkegaard’s view of the “dialectic” of temporal hope and eternal hope. Finally, we explore the treatment of hope in Either/Or as essentially involving a controlled, attentional element that anticipates some contemporary trends in the philosophy of hope.