This article studies politeness related terminology in the history of English with the aim of shedding some new light on the long diachrony of the folk notion of “politeness”, and at the same time we assess the usefulness of the research method which we call “metacommunicative expression analysis”. Metacommunicative expressions are words and phrases used to talk about aspects of communication, or a particular type of behaviour, such as “polite” or “impolite”. The semantic field of expressions that have been used in the history of English to talk about polite and courteous behaviour was charted with the help of the new research tool, the Historical Thesaurus of the Oxford English Dictionary and the Oxford English Dictionary. The frequencies of politeness related vocabulary items were then studied in the Helsinki Corpus. This exercise revealed areas of higher or lower density of politeness related vocabulary at particular points in the history of the English language and in specific prototypical text categories in the Helsinki Corpus. In the end, the analysis had to go back to the actual texts and interpret the specific politeness related vocabulary in their contexts. The analysis reveals the multifaceted nature of politeness and its manifestations at different points in the history of English and in different text categories.