In one exemplary aspect, a contextual user engagement system for automatically engaging in a conversation with a user is provided. A context manager manage, with at least one processor, the context of the conversation with a user. The context manager receives a user utterance, wherein the context manager calls the other modules of the contextual user engagement system to obtain information with respect to the user utterance. The context manager maintains a context object for a conversation with a user. The context manager automatically updates the context object based on an information detected by the other modules of contextual user engagement system. A content knowledge database stores a content knowledge of the contextual user engagement system. The content knowledge includes a history of interactions with the user. An information extraction engine extract information from a specified source based on a set of rules.