Andrei Astvastaturov, known to St. Petersburg audiences as a literary scholar and cultural commentator, has recently received much acclaim for his novels relating childhood memories from the 1970–1980s to more contemporary impressions of the autobiographical protagonist’s life in his hometown in a series of anecdotal sketches. The nostalgic tone of these narratives blending irony and sincere talk is familiar to readers of Russian postmodernist literature. However, within the context of aggressive state-supported nostalgia, Astvatsaturov’s version of this aesthetics gains new political undertones. Drawing on Alexei Yurchak’s analysis of the “performative shifting” of authoritative discourses in late-Soviet culture and on Mark Lipovetsky’s analysis of similar expressions and experiences of creativity and temporary freedom through the figure of the trickster, the chapter argues that Astvatsaturov’s narratives use comparable mechanisms to invert present-day “official” discourses of nostalgia. By analyzing three topoi of nostalgia in the novels—of Soviet childhood, the imperial Petersburg, and “new sincerity” - the chapter identifies the ways of mimicking and subverting its dominant expressions. Finally, the reading explores the ethical potential of this strategy which, it is suggested, lies in the novels’ re-evaluation of post-Soviet loss beyond a politics of victimization.