Resentment is a complex, multi-layered emotion, within which perceptions of unfairness and feelings of anger are central. When linked to politics, it has predominantly been associated with the alleged “crisis of representative democracy” and populism. However, recent studies have shown that resentment can intervene positively in people’s relations to politics and political institutions by facilitating certain types of political participation (Capelos & Demertzis, 2018). Despite this, the concept of resentment, and hence its role in contemporary representative democracy, is often poorly defined, with empirical investigations of its manifestation(s) remaining scarce. Borrowing a conceptualization of resentment as “resentful affectivity,” our article draws on the analysis of focus groups carried out in Belgium (2019–2020) with individuals where resentful affectivity is likely to be observed (i.e., contemporary movements of contestation such as the Yellow Vests, Youth for Climate, and individuals who occupy a socially disadvantaged position). We find that experiences of intense anger, fear, disappointment, and the unfairness of representative democracy, i.e., of how representative democracy works on the ground, coexist simultaneously with remaining hopes in the democratic system. We show how this complex blend of emotions confronts citizens with what we call a “democratic dilemma.” We document the different ways in which citizens cope with this dilemma and conclude by highlighting both the positive and negative ways in which resentment intervenes in the contemporary “crisis of representative democracy.”