Trainee translators are now being made more aware of the bi-cultural as well as of the bi-lingual character of their activity. One way of contributing to this essential intercultural awareness is through the widely exploited didactic tool of translation criticism. This paper draws its examples from Sue Townsend's hilarious portrait of an adolescent in the Britain of the early 1980s: The Secret Diary of Adrian Mole Aged 13 3/4 This text presents the translator, both at the stage of SL text decoding and TL transfer with considerable problems, mainly due to its high degree of cultural specificity (to the extent of presenting reception difficulties at various levels even for American readers). The question of how far this aspect of the ST was a determining factor in the Italian translator's limited success can be a rich source of reflection on both translation process and product that should provide the kind of stimulation students of translation need.