Knowing our contextualized (hi)story means being able to understand ourselves and how the world works. This kind of knowledge is key to self-awareness and self-empowerment, which also have a close connection with how we use language to communicate, to develop social interactions, to build relationships, and to project our identity. The diachronic evolution of languages is therefore a crucial part of a social being’s historical situatedness. The account of this evolution, i.e. historical linguistics, has traditionally focused on formal aspects of language as a grammatical system, investigating changes affecting or reflected in orthography, phonetics-phonology, morphology, syntax and vocabulary. More recently, however, scholarly attention has broadened its scope to include functional aspects of language use, such as strategies and conventions of communicative affordances over time, thus giving rise to historical pragmatics. In this special issue, the contributions encompass three main areas within historical pragmatics: language use in earlier periods (pragmaphilology), the development of language use (diachronic pragmatics) and causes of language change (discourse-oriented historical linguistics). In particular, the papers offer complementary insights into communicative practices, examining interactional strategies in classical languages, politeness phenomena in grammar and discourse, the evolution of discursive practices, the pragmatic use of lexemes and the teaching of sociopragmatics. Significantly, the issue presents a cross-linguistic approach, since it considers pragmatic phenomena in English, Korean, Italian, Slavonic languages, Ancient Greek and Latin, thus helping us understand how current discursive forms are in fact both unique and comparable in several languages and cultures.