By focusing on the degrees of politeness expressed by ‘please’ and its directive force, based on spoken data drawn from American and New Zealand English, this study sets out to present various systematic functional equivalences, observed at initial, medial, and final positions. The study stresses the importance of an integrated approach to sentential grammar and interaction, and discusses the necessity of construing an analytic scheme, which takes into account the concept of ‘position', when exploring a linguistic item in naturally occurring contexts.