Abstract Kierkegaard is interested in the problem of the meaninglessness of life. He regards this as an important modern phenomenon that must be taken seriously. This chapter begins a treatment of the second part of The Concept of Irony, where Kierkegaard examines different forms of what he calls “modern irony.” The positions that he looks at are very similar to that of the modern nihilist. We examine this analysis to see what insights it might hold for the modern problem of the absence of meaning in the twenty-first-century world. This chapter introduces Kierkegaard’s contemporary Johan Ludvig Heiberg, who tried to alert his age to the crisis of nihilism and subjectivism in a way that anticipates some of Kierkegaard’s considerations. This chapter goes through Kierkegaard’s critical assessment of Hegel’s understanding of Socrates and history to see where Kierkegaard follows Hegel and where he strikes out on his own.