The English variety spoken in York provides a unique opportunity to study the evolution of the English determiner system as proposed in the Definiteness Cycle (Lyons 1999). York English has three vernacular determiners that appear to represent different stages in the cycle: the zero article, reduced determiners and complex demonstratives of the type this here NP (Rupp 2007; Tagliamonte & Roeder 2009). Here, we probe the emergence and function of demonstratives in the cycle from the joint perspective of language variation and change, historical linguistics and discourse-pragmatics. We will argue that initially, the demonstrative reduced in meaning (Millar 2000) and also in form, resulting in Demonstrative Reduction (DR) (previously known as Definite Article Reduction (DAR)). This caused it to become reinforced. Data from the York English Corpus (Tagliamonte 1996–8) and historical corpora suggest that the use of complex demonstratives was subsequently extended from conveying ‘regular’ deictic meanings to a new meaning of ‘psychological deixis’ (Johannessen 2006). We conclude that survival of transitory stages in the cycle by several historical demonstrative forms, each in a range of functions, has given rise to a particular sense of ‘layering’ (Hopper 1991). Our analysis corroborates the idea that grammaticalization trajectories can be influenced by discourse-pragmatic factors (Epstein 1995; Traugott's 1995subjectification).