This paper highlights the philosophical and educational significance of expression in Ludwig Wittgenstein's Philosophical Investigations. When the role of expression is highlighted, we will be better able to appreciate Stanley Cavell's insistence that: (i) Wittgenstein offers ways of responding to, though not a refutation of, the problem of skepticism concerning other minds, and (ii) Wittgenstein's writing style is an important aspect of his philosophy. The educational implications of this appreciation will be explored with reference to the lives of adolescences.