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We know little about Sigmund Freud’s adolescence compared to the other periods of his life. However, adolescence occupies a certain place in some autobiographic dreams or in the correspondence with his young friend E. Silberstein. We support the links between these biographical points and their different interpretations in psychoanalytic theory. We explore in particular the father–son relationship during adolescence in an intergenerational perspective: Freud with his father and Freud as a father of young boys. We address the idea that, during his adolescence, confronted with his post-pubertal sexuality, Freud did not feel the support of his father. Rather, he felt distraught faced with his boundless drives, alone with his sexual abstinence and moralism.