Im/politeness has attracted considerable attention (starting with Lakoff 1973; Brown and Levinson 1978; Leech 1983) and has kept expanding rapidly with the discursive turn (Eelen 2001; Mills 2003; Watts 2003; Bousfield 2008; Locher 2008). There is a growing interest in examining im/politeness from a number of perspectives, e.g. society, gender, cross-cultural etc., and multiple definitions have been proposed, however, impoliteness as such has not had a distinct theoretical framework yet. This study investigates impoliteness through drama translation data. It focuses on manipulation of im/politeness in target versions of a playtext, in terms of gender, and examines how humour may be facilitated through such shifts. The aim is to confirm that impoliteness does interact with gender (Mills 2003), and that humour creation draws on reversed gender stereotypes. It also shows that power (ensuing from reversed gender stereotypes) interacts with impoliteness strategies, to manifest humour in the target versions. The study uses Bousfield’s (2008) model to account for im/politeness shifts, between the two versions. Oscar Wilde’s Lady Windermere’s Fan (1892) is a comedy and a satire targeting the aristocratic society of the time. The two Greek translations of the play (2006 by Karhadakis and 2010 by Belies) are a most suitable context for examining how impoliteness interacts with power distance and gender to create humour, because of its humorous aspects and cross-gender talk. The paper also intends to show impoliteness scholarship that translation has a rich potential for deciphering or confirming pragmatic aspects of the phenomenon, which are elsewhere pursued through monolingual research.