Abstract: A conversational assistant for conversational engagement platform can contain various modules including a user-model augmentation module, a dialogue management module, and a user-state analysis input/output module. The dialogue management module receives metrics tied to a user from the other modules to understand a current topic and a user's emotions regarding the current topic from the user-state analysis input/output module and then adapts dialogue from the dialogue management module to the user based on dialogue rules factoring in these different metrics. The dialogue rules also factors in both i) a duration of a conversational engagement with the user and ii) an attempt to maintain a positive experience for the user with the conversational engagement. A flexible ontology relationship representation about the user is built and stores learned metrics about the user over time with each conversational engagement, and then in combination with the dialogue rules, drives the conversations with the user.