Abstract: A system (100,300) and method (500,600) for delivering advertising selected for a target audience to the target audience are disclosed. The system (100,300) includes an advertising selector (206,306) configured to select one or more advertisements (114,314), which may be interactive and include click-through interaction features (315). The advertisements (114,314) are delivered to user devices (106,107,108,306,307,308) of members of an audience. A detector (208,408) is configured to determine a usage rate, and to detect whether predetermined thresholds for usage were met. Where they were not, a database-mining engine (209,409) determines one or more additional content offerings where at least a portion of the usage set of members was co-mingled, and to then determine one or more future content offerings corresponding thereto. An advertising placement opportunity generator (214,414) then schedules advertisements to be delivered during the future content offerings.