Artifice and authenticity are conflictingly related in the extroverted and stylised displays of feeling in the texts of Laurence Sterne and Ignatius Sancho. Whereas Sterne employs aesthetic playfulness to set himself apart from literary predecessors, Sancho uses it to claim a part in the culture of taste and sensibility. This chapter reads Sancho and Sterne’s literary adoption of a digressive tonality distinctly not as imitative but as entangled. The scenes dealing with slavery in Tristram Shandy and A Sentimental Journey are tied into more bawdy episodes. While not necessarily only sentimental, they still elude ideas of political solidarity. Sancho’s interjections of emotional concern in his published letters in turn not only highlight his capacity to feel (as well as his attachment to his family); in adopting the Sternian digressive dash, he does not adhere to the usual linear form of redemptive abolitionist writing and displays a uniquely Black aesthetic voice, albeit one that also reproduces deprecating sentimental tropes. This needs to be read as more than simply epigonic. Sancho’s digressive tone, it will be argued, intervenes more fundamentally into the sentimentalist romance with the cultured, feeling subject of modernity, while Sterne remains more elusive in his aestheticised divagations.