Virginia Woolf's sentences prompt us – indeed, they train us with continued engagement – to become more agile, creative and discerning readers. Many of Orlando's sentences press this training even further, enjoining us to problematise reading itself as a notion or concept and to reflect on our own reading habits and practices. In this chapter, I examine one of these sentences and explore how its encouragement and theorisation of a reflexive, curious and ethical mode of reading opens us to a host of disturbing and disturbingly related contexts: namely, the mostly unexamined influence of Sir Thomas Browne on Woolf's thought, the philosophical implications of her fascination with ruins and remains, as well as the legacy and contemporaneity of colonialist and imperialist violence. Problems of reading – what it is or might be, how one might go about it, what sort of obstacles might interrupt it – link together these and other contexts in Orlando, which suggests that some acts of reading (perhaps our own, perhaps even Woolf’s) are complicit with human cruelty, violence and indifference.