This article explores claims about how to understand others. It does so through ethnography of ways cultural producers and their apprentices struggled and colluded over what constitutes a true reading or empathic performance of another's words. The linguistic forms up for interpretation were those in Russian personal ads. Like many other forms in the region, personal ad texts are vulnerable to shallow readings as mere market imports, and so the article first unpacks Transition and Cold War ideologies in order then to discuss interactions that lay out alternate formulae for reading the ads. These latter hermeneutics are no less ideological—their makers also separate, condense, and combine “variables” to ratify the reality of categories (e.g., generation, nation, sentiment). Still, to examine how they do so does undermine Cold War paradigms and moreover suggests how people ground meta‐discourse about misunderstanding itself. The article draws from fieldwork at the Russian Academy for the Theatrical Arts in Moscow in 2002–3 and 2005, as well as from other field, archival, and media work in Russia since 1988. [hermeneutics, intertextuality, performance, sentiment, Russia]