This study addresses a commonly trivialised and suppressed, but nonetheless increasingly manifest phenomenon in Western culture: boredom. It begins with a confession of its author, who in an autobiographical “Chronicle of a bored life” describes the boredom that has plagued him since his childhood and which has led him to investigate the peculiarity of this phenomenon. This alleged peculiarity stems – as is argued in a preliminary consideration – from a crucial prerequisite for its occurrence: boredom seems to be the downside of happiness and well-being, or, put on more prosaic terms: of prosperity. Those who are tormented by grief will not experience boredom; nor will those persecuted, nor those who suffer from illness or poverty. To paraphrase the biblical book of Ecclesiastes: “He who increases wealth, will increase boredom.” In the First Chapter, some paradigmatic examples of this predicament are described, such as the Roman aristocrats, whose taedium vitae made them flee from Rome to find distraction in their country houses in Tibur. After getting bored in the country, however, they hastily returned to the hectic entertainment of the Colosseum. Centuries later, Pascal and Shakespeare elaborated on the embarrassing predicament of the monarch, who may seem to be the most enviable of men, but who surrounds himself with court jesters and dancers, goes hunting and plays cards in order to avoid boredom. In spite of his kingship, he is incapable of being at ease when alone in his chambers, with nothing to distract him. And perhaps the king is just an extreme case of today’s prosperous hu-man condition: the configuration of restlessness, a search for diversion and then, time and again: boredom. The major part of the First Chapter thus consists of “Discourses of the bored”: a collage of the remarkably ‘rich’ history of boredom in Western culture, composed of various philosophical and literary quotations reaching from Seneca and early Christianity, through Burton, Voltaire, Büchner, Kierkegaard, Schopenhauer, Baudelaire, Eliot and Beckett, to Ellis and Houellebecq.