The ancient problem of whether our asymmetrical attitudes towards time are justified (or normatively required) remains a live one in contemporary philosophy. Drawing on themes in the work of McTaggart, Parfit, and Heidegger, I argue that this problem is also a key concern of Kierkegaard’s Either/Or (1843). Part I of Either/Or presents the “aesthete” as living a temporally volatilized form of life, devoid of temporal location, sequence and direction. Like Parfit’s character “Timeless,” these aesthetes are indifferent to the direction of time and seemingly do not experience McTaggart’s “A-Series” mode of temporality. The “ethical” conception of time that Judge William offers in Part II contains an attempt to normativize the direction of time, by re-orienting the aesthete towards an awareness of time’s finitude. However, the form of life Judge William articulates gives time sequentiality but not necessarily the robust directionality necessary to justify (and make normative) our asymmetrical attitudes to time. Hence while Either/Or raises this problem it remains unanswered until The Concept of Anxiety (1844). Only with the eschatological understanding of time developed in The Concept of Anxiety does Kierkegaard answer the question of why directional and asymmetrical conative and affective attitudes towards time are normative.