Samuel Beckett’s “Dante postcards” record the first three smiles to be found in the Purgatorio. In doing so, Becket draws attention to a gesture that has recently received significant critical attention within Dante studies. These postcards suggest Beckett’s alertness to the complexity of face to face encounters within the Commedia, while also providing an opportunity to consider the extent to which facial expressions are significant within Beckett’s own writing. In this essay, I argue that the postcards can be read alongside Beckett’s early novels, in particular, Murphy (English 1938, French 1947) and Watt (English 1953, French 1968). Moreover, I explore the extent to which Beckett's readings of Dante are multifaceted in that they demonstrate the extent to which he was both inspired by, and yet also at odds with, his Italian predecessor.