Although there is a body of research on impoliteness, cross-generational variation in the perception of impoliteness has received scant attention. To address this gap, the present chapter outlines the conceptualization of impoliteness and reviews the scholarship on the perception of impoliteness, including studies in Persian-speaking contexts. Against this backdrop, it reports on an empirical study of the cross-generational perceptions of impoliteness of the Persian requestive speech act. A written discourse completion task (WDCT) was used to collect the data. The participants were asked to rate each request on a five-point Likert scale and provide explanations for their ratings. The analysis of the data revealed that the participants applied seven criteria in rating the impoliteness of requests, including overall politeness, directness and indirectness, register choice, query preparatory and softeners, social distance, power, and imposition. Although the three generations’ perceptions of impoliteness were framed by these criteria, they varied in their perceptions of the intensity of impoliteness and the weight they assigned to each criterion. The chapter concludes that cross-generational differences can frame the perceptions of the intensity of impoliteness rather than the criteria for evaluating it.