To see how education can offer a space for contending with the ubiquitous problem of boredom, I first need to begin to define what boredom is and understand how it constitutes a “problem” for the pursuit of a flourishing life. The most vexing kind of boredom is what Heidegger describes as “existential boredom,” characterized by a disenchantment with life and a struggle to find meaning. In contrast to situational boredom, which ebbs and flows depending upon external conditions, existential boredom is often an enduring condition that, while affected by material conditions, is not reducible to them. Situational boredom points to a clear and immediate solution in some kind of action, while the cure for existential boredom is often unclear. Even more problematic, as I will argue, the avoidance of situational boredom intensifies existential boredom. The pervasive cures for situational boredom are the causes of existential boredom.