A targeted advertising system uses a machine learning tool to select an asset for a current user of a user equipment device, for example, to select an ad for delivery to a current user of a digital set top box in a cable network. The machine learning tool first operates in a learning mode to receive user inputs and develop evidence that can characterize multiple users of the user equipment device audience. In a working mode, the machine learning tool processes current user inputs to match a current user to one of the identified users of that user equipment device audience. Fuzzy logic may be used to improve development of the user characterizations, as well as matching of the current user to those developed characterizations. In this manner, targeting of assets can be implemented not only based on characteristics of a household but based on a current user within that household.