Though formally reunified in 1990, the Federal Republic of Germany in many ways remains a deeply divided country. East Germans face higher unemployment rates, lower wages, worse access to healthcare, and decaying infrastructure among other challenging circumstances. Significant portions of the East German population feel alienated from the political system, with the most established parties – largely dominated by West German politicians – seemingly unable to connect with the East German electorate. Meanwhile, the communist successor party Die Linke and the right-wing populist Alternative für Deutschland (AfD) frequently gain pluralities – in some cases even majorities – of the East German vote in state and federal elections. In their campaigns, these parties often evoke sentiments of Ostalgie, nostalgia for the socialist past, and present themselves as East German Volksparteien, people’s parties. In this paper, I analyze the rhetoric of members of the German Bundestag towards the communist German Democratic Republic (GDR) and East Germany as a region. A sentiment analysis of all speeches given in the Bundestag between 1990 and 2021 reveals that representatives of PDS/Die Linke and the AfD are significantly more positive in their rhetoric towards East Germany and the GDR than their peers from the established, more centrist parties. Further, whether or not a representative was born in East Germany has little effect on their expressed sentiment towards the region and its communist past. Through natural language processing, this study contributes empirically to scholarly conversations around alienation, representation, and populism in postcommunist East Germany.