Recent German literature and film reflect (on) the loss of promise for both self and societal realization under not one but two ideological regimes: socialism and capitalism. The socialist utopia never arrived; was the capitalist meritocracy ever there? The guarantee of some kind of telos—an endpoint, a ‘good life,’ towards which everyday life was supposed to be going—has thus been frustrated on two historical fronts. I take this parallel as grounds for juxtaposition across historical, affective and aesthetic lines, investigating the waning of teleological promise in the final two decades of the GDR and the last twenty years of 21st century Germany. I present the ‘post-teleological’ as a concept for trans-ideological and cross-temporal comparison, offering a new lens through which to draw texts into unconventional comparative constellations. The questions that this concept raises are the following: how do literature and film translate the affective experience of ideology’s failing persuasive power as aesthetic experiences? How does a juxtaposition of disparate contexts further our understanding of individual works’ break with hegemonic conventions to deliver critique? And how do discrete formal strategies pass comment on the movement (or non-movement) of history? I interrogate literary works by Brigitte Reimann, Irmtraud Morgner, Kathrin Röggla and Shida Bazyar, and films by Konrad Wolf, Evelyn Schmidt, Christian Petzold and Valeska Grisebach, to track the arc of ideological promise’s decline across both periods. I query what affective and aesthetic practices may follow the sense of stasis which accompanies the disappearance of an alternative to neoliberal capitalism.