Kierkegaard’s aesthete, named only as A, continually laments the lack of meaning in his life. He suffers through passions that flare up and quickly die away, leaving him in a melancholic state. His mode of being is on display in the Diapsalmata, the fragmentary writings at the start of Either/Or. In this chapter, we examine why he avoids becoming consistently engaged in the world and remains trapped within his alienated melancholia. We offer a general account of melancholy, arguing that melancholia is an existential condition that must be understood in terms of the metaphysics of possibility. We also provide a sympathetic interpretation of A’s melancholy, rather than placing blame upon him, because melancholia attunes us to certain aspects of the world and of human existence. The aesthetic life has epistemic, moral, and aesthetic worth on its own terms, so a person may legitimately decide to remain melancholic. This avoids compromising our possibilities, makes us receptive to the suffering of others, and may inspire creative activity such as writing poetical fragments.