Stanley Cavell and Cora Diamond are two contemporary American philosophers deeply influenced by the work of the early and the late Wittgenstein. Cavell and Diamond read Wittgenstein, particularly, as a romantic thinker open to the disappointments and the difficulties of our lives in language. For Cavell, the Philosophical Investigations is remarkable for its call to meaningful and responsible expression; in recognising the fragility and disappointment of everyday expression, Wittgenstein in fact calls his reader to linguistic and bodily responsiveness. For Diamond, both the Tractatus Logico-Philosophicus and the Philosophical Investigations recommend a distinctively "realistic spirit", one where we are aware of our finitude, aware of our fleshiness, aware always that we inhabit a body and that we are never immune from pain. It is the purpose of this chapter to explore further these romantic interpretations of Wittgenstein and to consider particularly their important educational implications.