The paper investigates the semantic and pragmatic properties of the postpositive definite article and demonstratives in Serbian TimokLužnice dialect. In the literature, there is a consensus on the evaluation that the definite article morpheme functions both as a demonstrative and an article (BELIĆ 1905; STANOJEVIĆ 1911; BOGDANOVIĆ 1979; ĆIRIĆ 1893) and that “the demonstrative nuances still exist in the article” (VUKADINOVIĆ 1996: 203), without a thorough analysis in what conditions the utterance receives a demonstrative or a definite interpretation. We will show that there are contexts in which either the article or the demonstrative is pragmatically acceptable for native speakers. Namely, the results of a conducted research in which the speakers evaluated the pragmatic acceptability of an utterance in a given context on a 3point Likert scale unequivocally show that the definite article is used to mark discourse-old relational nouns’ referents, uniqueness, associative anaphora and generic noun phrases, while demonstratives regularly appear with contrastive deictic referential phrases and in emphatic nonepithetic contexts.