This article presents the results of an exploratory empirical study into the perception of conventionally indirect requests in British English and Peninsular Spanish, given the high incidence of the pragmatic category over others in its encoding of politeness in both related and unrelated languages (cf. Blum-Kulka et al., 1989). More specifically, the article focuses on the similarities and differences between Britons and Spaniards with regard to the speaker's assumed expectations of compliance in choosing from the conventionally indirect spectrum. In other words, the focus is on how (un)certain the speaker was that the addressee would comply with the request when s/he chose a particular conventionally indirect request. The data for this study were collected via an open role play, post-performance interviews and questionnaires. The results obtained show that, in comparable situations, the Spaniards were generally more certain that the addressee would comply with the request than the Britons. It is argued that conventional indirectness appears to reflect different social meanings in English and Spanish and that such differences should be taken into account when analysing the realization patterns of pragmatic categories in language.