Abstract: The present web-based system and methods enabled by an application executable on a computing device of the system allow subscribers to develop a private circle and interactive family & friends tree within a private social network, and to schedule delivery of selected content to a designated recipient, either on a future date or upon occurrence of a future event having a date unknown to the subscriber. The system may determine a delivery date for the selected content, even if no date is specified by the subscriber, based on data obtained from other subscribers to the private circle and/or machine learning analysis, and may validate the delivery date before delivering the content. The system may enable parent subscribers to the private circle to add newborn and/or unborn children to the private circle, and may enable subscribers to prepare a digital will and integrate the will with the subscriber's account in the private circle.