More than half of Adrian’s diary entries (by Sue Townsend, 1982, 1984, 1988, 1991, 1993 and 1999) encompass two decades of the protagonist’s maturing process and existence, in a working class setting. These cover different periods of the British History and sociopolitical events: from Margaret Thatcher’s takeover to Tony Blair’s government. Indeed, Adrian finds it difficult to conform to a way of life which he holds up as trivial. Besides, “Englishness” has acquired, in his unexpected conservative stance, a multicultural dimension for much of Adrian’s disenchantment. Therefore, he is fiercely committed to preserve the all-British standards, evidenced in his behaviour and discursive practices, by means of a witty dialogue, irony, hyperbole, and parody. The aim of this paper is to bring to the fore some of the protagonist’s sociocultural references and stylistic choices which challenge readers with humorously “unusual and unexpected events to the ‘maps of meaning’ (Hall et al., 1978: 54-55), that already form the basis of their cultural knowledge” of everyday language. Readers identify strings of continuity, on the one hand, and of rupture between the scheming of the old empires and the new goals of global capitalism, on the other. Perhaps Townsend’s premise against life’s “alogical” course of events led her to create a fictional character for whom humour may be suggestive of “a certain ideal image of the world” (Critchley 2002: 87-90).