By tracing the political resonances of the concept of the “real” in its different theorizations – particularly in relation to singularity and border, and its opposite, multiplicity and entanglement – we highlight in this paper the existing relation between epistemological frameworks and political imaginaries or horizons. In order to undertake this task, we offer a critical conceptual triangulation between Chantal Mouffe’s account of the current “populist moment” and the theorization of the real in the work of Jacques Lacan and Maurice Merleau-Ponty. By mobilizing a dialogue between psychoanalysis and (post-)phenomenological thinking, we suggest that if the real is not conceptualized as an ontological negativity that the empty signifier needs to tame, but as an aesthetic, embedded, and embodied experience of multiplicity, we can think beyond the logics of dichotomist antagonism and instead embrace the ethos of fleshy relationality that informs our co-dependence, precarity, and vulnerability.