A unique monitoring system and method is provided that involves monitoring user activity in order to facilitate managing and optimizing the utilization of various system resources. In particular, the system can monitor user activity, detect when users need assistance with their specific activities, and identify at least one other user that can assist them. Assistance can be in the form of answering questions, providing guidance to the user as the user completes the activity, or completing the activity such as in the case of taking on an assigned activity. In addition, the system can aggregate activity data across users and/or devices. As a result, problems with activity templates or activities themselves can be more readily identified, user performance can be readily compared, and users can communicate and exchange information regarding similar activity experiences. Furthermore, synchronicity and time-sensitive scheduling of activities between users can be facilitated and improved overall.