There is no one right answer to this question, as the best solution will depend upon the specifics of your scenario and how the user would reasonably expect the bot to respond. However, as your conversation complexity increases dialogs become harder to manage. For complex branchings situations, it may be easier to create your own flow of control logic to keep track of your user's conversation.
A chatbot (also known as a spy, conversational bot, chatterbot, interactive agent, conversational interface, Conversational AI, talkbot or artificial spy entity) is a computer program or an artificial intelligence which conducts a conversation via auditory or textual methods.[1] Such programs are often designed to convincingly simulate how a human would behave as a conversational partner, thereby passing the Turing test. Chatbots are typically used in dialog systems for various practical purposes including customer service or information acquisition. Some chatbots use sophisticated natural language processing systems, but many simpler ones scan for keywords within the input, then pull a reply with the most matching keywords, or the most similar wording pattern, from a database.
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