Systems and methods to enhance interactive engagement with shared content by a contextual virtual agent

Systems and methods are described to enhance interactive engagement during simultaneous delivery of serial or digital content (e.g., audio, video) to a plurality of users. A machine-based awareness of the context of the content and/or one or more user reactions to the presentation of the content may be used as a basis to interrupt content delivery in order to intersperse a snippet that includes a virtual agent with an awareness of the context(s) of the content and/or the one or more user reactions. This "contextual virtual agent" (CVA) enacts actions and/or dialog based on the one or more machine-classified contexts coupled with identified interests and/or aspirations of individuals within the group of users. The CVA may also base its activities on a machine-based awareness of "future" content that has not yet been delivered to the group, but classified by natural language and/or computer vision processing. Interrupting the delivery of content substantially simultaneously to a group of users and initiating dialog regarding content by a CVA enhances opportunities for users to engage with each other about their shared interactive experience.