This chapter provides a comparative quantitative and qualitative analysis of personal (‘h-’ type) and demonstrative (se-type) pronoun usage in the Old English dialects of West Saxon, Mercian and Old Northumbrian. The findings reveal that se-type pronouns were already frequently used in personal pronoun functions in the North prior to significant Norse contact. The same overlap in function is found in Mercian. Late West Saxon also employed local diphthongal demonstrative variants as personal pronouns outside the heavily Scandinavianised regions. The chapter argues that the increased use of demonstratives as personal pronouns stemmed from internal linguistic changes, such as the breakdown and reorganisation of the Old English demonstrative system and a preference for phonetically stronger forms in prosodically prominent positions.