Politeness is of particular importance in health care contexts, where a number of international agreements and consensus statements formulated by policy makers demand that accord should be maintained, agreement should be solicited, and an attitude of respect be sustained especially when burdensome or intimate matters are being discussed. This paper explores the patterns of politeness in a corpus of material from a UK study of telephone encounters between NHS Direct health advisers and callers presenting with a need for advice over medication. In the opening sequences of interaction the questions that advisers asked the callers often included multiple politeness markers, for example through terms such as "may" and "just", as in "may I just ask you?". Politeness markers were often multiply layered, falling into three part structures which occurred when mundane information such as callers' names and telephone numbers were being elicited. Where more intimate matters were at stake, advisers minimized imposition and, arguably, undertook rapport building by means of preambles to the question such that the impending intrusion is accounted for, explained or mitigated. A potentially problematic question could also be followed up by further relational work and humour. There are important implications here for understanding politeness itself, especially where it is displayed by an institutionally more powerful or symbolically credentialed interactant towards one who is less advantaged.