Current chatbot systems cannot understand enough different topics to converse with students who have questions about college admissions, financial aid, courses, and other topics on the path to and through college. Current chatbots also have a hard time understanding misspellings, slang, and context-specific language, e.g., like the language used by students. “Learning” new topics is very time-consuming for current chatbots. And it is difficult for administrators to participate in student conversations carried out in part by current chatbots. To address these technical problems, an inventive chatbot uses a natural language processor (e.g., a neural network) to receive, classify, and respond to queries on thousands of different topics. An inventive chatbot can also request real-time assistance from an administrator when faced with a difficult query and learn on-the-fly from the administrator's response. This ability to learn on-the-fly gives inventive chatbots significant performance advantages over current chatbots.