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This article explores the complexities of male desire in adolescence. These formative years offer boys many opportunities to discover desire as a creative, pleasant experience, on both the physical and psychological levels. The accumulation of these experiences brings about a sort of initiation into maleness, in which the boy accepts and welcomes his changing body as he approaches adulthood. Nevertheless, at several turning points along this path, desire can topple over into destruction. Sabina Spielrein’s fundamental essay on the theme of creation and destruction supports these ideas. An example drawn from the Netflix series Adolescence shows a contemporary representation of it. The Sorrows of Young Werther by Goethe, written over 250 years ago, is still a relevant source for understanding the tragic collapse that may upset this balance of desire. In Goethe’s story, a young man’s desire leads to his self-destruction. Finally, the author presents a clinical example that shows the fragility of the terrain the male adolescent must tread, and the points where desire may push him over the brink into madness. The author suggests that real contact with the father is important. He introduces the concept of the “scarecrow father” to show factors that are likely to lead to a destructive outcome, instead of a creative one, for adolescent male desire.