This paper examines a small corpus of advertisements and letters about marriage that appeared in late eighteenth-century copies of The Times. A pragmatic, discourse-analytic approach is used to investigate how these texts were linked to a context of ‘politeness’ that was composed of three central (and partly overlapping) values: formality, distancing achieved through impersonalisation, and discernment (defined as apparent concern for the well-being of others). It is argued that these text-context links had a performative or creative aspect; the politeness context structured but did not determine the use of language forms to communicate meanings. The paper focuses on how language was used to sever and then to re-align text-context links, or to provide metadiscursive commentary that qualified the politeness context, or to create ambiguity by forging links with equally plausible but incongruous contexts.