This is where most applications of NLP struggle, and not just chatbots. Any system or application that relies upon a machine’s ability to parse human speech is likely to struggle with the complexities inherent in elements of speech such as metaphors and similes. Despite these considerable limitations, chatbots are becoming increasingly sophisticated, responsive, and more “natural.”
Chatting with a bot should be like talking to a human that knows everything. If you're using a bot to change an airline reservation, the bot should know if you have an unused credit on your account and whether you typically pick the aisle or window seat. Artificial intelligence will continue to radically shape this front, but a bot should connect with your current systems so a shared contact record can drive personalization.