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I think Ruby/Sinatra itself is very easy to use because it uses more like natural language. However, it takes so many steps to set up for running a chatbot. 

The biggest challenge I had on this project was designing more human-like conversations. So far NurieBot can only chat the limited number of conversation that I pushed. I think I need another Gem or code that help NurieBot learn and mimic my texts.  

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