Representations of the boy in Dutch educational literature shift considerably during the twentieth century while educational goals remain importantly unchanged. Optimism in education seen before the Second World War diminishes after the war as a result of social changes. While representations of boys take on increasingly negative tones, boys themselves may be changing little. This is suggested by the goals of education that remain constant during the entire century, goals which aim to free the boy as much as possible from troublesome behavior as mischief. Pedagogical aims to have boys adopt desired behavior, like courteousness, change during the 1970s and stress those of care and emotional strength. However, boys’ adoption of caring behaviors progresses so slowly the boy, often embraced as the hope of the fatherland in the first half of the twentieth century, is increasingly seen as a problem at the end of it.