This disclosure covers systems and methods that generate and train a chatbot to automatically communicate with users concerning subjects related to a digital advertisement received for distribution. In particular, the disclosed systems and methods train a chatbot to simulate common conversation exchanges from messaging threads associated with previous digital advertisements that are similar to a received digital advertisement. By training the chatbot to simulate such conversations, the disclosed systems and methods create a chatbot that can immediately respond to a user's inquiries concerning the received digital advertisement and tailor automated exchanges that further the objectives of an advertiser or merchant associated with the received digital advertisement.