Chat bots are finding increasing usage these days in applications ranging from simple automated FAQ’s to sophisticated e-commerce buying recommendations. The technology powering these bots has undergone tremendous improvements thanks to new age sciences such as Machine Learning, AI and Natural Language Processing. Although chat bots have come quite far in effectiveness and imitating real humans, there’s still lapses and areas where they can be improved in order to make them much more powerful and closer to human interaction. This is the main aim of the proposed work where one such limitation has been considered and attempt to address it by utilizing Natural Language Processing.