In accordance with aspects of the inventive concept, provided is a monitoring and alert system that enables one or more monitoring individuals, e.g., parents, to monitor social media usage, Internet usage, application usage, content, communications, location, and/or other aspects of one or more other monitored users, e.g., their children. The monitoring and alert system can utilize social media, electronic communications, cellular data, positioning data, and navigation data, as examples, relating to and/or generated from a monitored user's activity on its mobile device to acquire data used to generate alerts to the corresponding monitoring users.