This essay detects a genre of non-fiction, which it coins as Stadtschmerz. In this genre, middle class residents who experience alienation due to gentrification turn this experience into stories of loss and guilt (for being the target group of gentrification). This essay explores four canonical texts of Stadtschmerz from the mid-19th century to the present; the authors explore the gentrifying city as flâneurs and report on their findings in a feuilleton. As such, the essay shows how through expressing Stadtschmerz the middle-class attempts to cope with the making of the middle-class city. In this way, Stadtschmerz neutralizes the positionality of the writer and his readership within processes of gentrification. Furthermore, it offers readers voyeurism into the lives of the displaced lower classes. Lastly, Stadtschmerz processes middle-class anxiety amid gentrification. A deconstructive analysis of Stadtschmerz tells us that the experience of gentrification is above all a hot topic for the middle-class itself.