Empathy is an integral aspect of human existence. Without at least a basic ability to access others’ affective life, social interactions would be well-nigh impossible. Yet, recent studies seem to show that the means we have acquired to access others’ emotional life no longer function well in what has become our everyday business – technologically mediated interactions in digital spaces. If this is correct, there are two important questions: (1) What makes empathy for frequent internet users so difficult? and (2) (...) What can we do to alleviate the negative consequences? Correspondingly, the aim of this paper is twofold. First, we identify structural differences between offline and technologically mediated interactions that can explain why digital empathy is harder to achieve. Second, drawing on the literature on ‘situated affectivity,’ we consider the idea of modifying digital spaces in ways specifically designed to ‘scaffold’ empathy where our evolved mechanisms fail. Section 2 argues that empathy is requires interpreting the behavior of embodied subjects. Section 3 identifies three factors that are crucial for this interpretative endeavor: the empathizer’s affective repertoire, their perceptual input, and their background knowledge. Section 4 argues that technologically mediated interactions differ from face-to-face interactions with regard to these factors in ways which render our evolved empathy mechanisms less effective in the digital world. Section 5 introduces the idea that situational factors can serve as ‘empathic scaffolds,’ i.e., as ‘tools’ that can ‘shape’ people’s empathic reactions. Section 6 wraps up the main line of reasoning, responds to objections and invites further scholarship. (shrink)