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.”
In 1950, Alan Turing's famous article "Computing Machinery and Intelligence" was published, which proposed what is now called the Turing test as a criterion of intelligence. This criterion depends on the ability of a computer program to impersonate a human in a real-time written conversation with a human judge, sufficiently well that the judge is unable to distinguish reliably—on the basis of the conversational content alone—between the program and a real human. The notoriety of Turing's proposed test stimulated great interest in Joseph Weizenbaum's program ELIZA, published in 1966, which seemed to be able to fool users into believing that they were conversing with a real human. However Weizenbaum himself did not claim that ELIZA was genuinely intelligent, and the introduction to his paper presented it more as a debunking exercise:
Malicious chatbots are frequently used to fill chat rooms with spam and advertisements, by mimicking human behavior and conversations or to entice people into revealing personal information, such as bank account numbers. They are commonly found on Yahoo! Messenger, Windows Live Messenger, AOL Instant Messenger and other instant messaging protocols. There has also been a published report of a chatbot used in a fake personal ad on a dating service's website.
“There is hope that consumers will be keen on experimenting with bots to make things happen for them. It used to be like that in the mobile app world 4+ years ago. When somebody told you back then… ‘I have built an app for X’… You most likely would give it a try. Now, nobody does this. It is probably too late to build an app company as an indie developer. But with bots… consumers’ attention spans are hopefully going to be wide open/receptive again!” — Niko Bonatsos, Managing Director at General Catalyst