Chapter 3 explores the characteristics of pragmatic markers and focuses on both their function during a particular period and their development over time. Diachronically, pragmatic markers develop from content words, phrases, or clauses that gradually acquire a distinctive syntactic form and discourse-pragmatic functions and follow various pathways, from adverb > conjunction > pragmatic marker, from sentence-internal adverb > sentential adverb > pragmatic marker, from main clause > ambiguous clause > parenthetical, from adverbial or imperative clause > pragmatic marker. A number of examples of such pathways are provided, where it is shown that the historical data may be messy and require nuanced interpretation. For clausal pragmatic markers, the “matrix clause hypothesis” is critically examined. The process of language change that best accounts for the development of pragmatic markers, including lexicalization, pragmaticalization, grammaticalization, and cooptation, is still a matter of debate, though the majority view is that if “grammar” is broadly understood, pragmatic markers are best seen as undergoing grammaticalization (decategorialization, desemanticization).