Jesse Rosenthal states in the introduction to the 2017 special issue of Genre : ‘data is a big deal right now. We cannot talk about data and the novel without recognizing the particular importance that the question of data has in literary studies’ (2017, p. 4). This paper is positioned at the intersection of Literary Studies and Computer Science. It explores the appli cation of computer based analysis to novels from the long eighteenth century (an historical period between approximately 1640 to 1830) and, specifically, examines the insights that are gained by using these tools to compare novels by Jane Austen and Maria Edgeworth. It also considers the challenges these methods may present for Humanities scholars, and the benefits of combining computational approaches with close reading. The title of this paper comes from the film ‘When Harry Met Sally...’ (1989). The li ne at the heart of the film proposes that ‘men and women can’t be friends because the sex part always gets in the way’, before ultimately demonstrating that, for Harry and Sally, combining sex with friendship leads to a positive relationship. This analogy echoes some of the arguments against the use of digital analysis in literary studies, or, to rephrase it ‘literary studies and computer science can’t be friends because the tech part always gets in the way’, but it also suggests a possible way forward.