This paper explores the relation between grammatical gender and speakers’ cognition based on an experimental task conducted with Hindi speakers. Hindi is an Indo-Aryan language with two gender system. Data was collected from sixty native speakers of Hindi, aged 18–23 years from Delhi and its adjoining Hindi-speaking areas. Participants were provided a task-sheet with instructions in Hindi and with 102 lexical items divided into six semantic categories. They were to choose two items from each category, imagine them as personified, locate them in a relationship including kinship, social and professional relation and mark the role of both items in each pair. Analysis of the data showed that 62.3% of the total individual items were gendered, out of which 80.5% were assigned gender in consonance with grammatical gender. The remaining 37.7% of the items were placed in ambiguous roles like friend, teacher and student. Among the item pairs, a prototype like pattern was observed across two dimensions—inter and intra semantic categories. Some pairs figured much more than others and the frequency correlated positively with their usage in everyday and literary contexts. Results clearly indicate a significant positive correlation between grammatical gender and assigned gender. The study shows that grammatical structure and frequency of occurrence of the variable (object/object pair) through everyday language use, interact in complex and circular ways to shape speakers’ cognition. The chapter concludes that even a conventionally well-defined grammatical category neither functions independent of other cognitive domains nor does it manifest uniformly within domains of linguistic usage of a single language including pedagogical domains like the texts used by native speakers.