This paper investigates the affinities between V2 in Old English, the Spec, CP position, and the deictic þ/s-system (demonstratives se/seo/þæt as well as an etymologically related set of time, place and manner adverbs þa ‘then’, þonne ‘then’, þær ‘there’, þus ‘thus’, swa ‘so’, swylc ‘such’). The interrelations between V2 syntax and an articulated demonstrative paradigm create efficient systems for expressing topic shift and topic continuity. In the course of Middle English, a number of developments conspire to break the system down: the loss of gender and the loss of V2, leading ultimately to a loss in specific reference of the þ/s-elements and a restructuring of discourse relations, with relative pronouns taking over the role of topic shifters.