Abstract: A system and method for selecting and presenting personally targeted entities such as advertising, coupons, products and information content, based on tracking observed behavior on a user-by-user basis and utilizing an adaptive vector space representation for both information and behavior. The system matches users to entities in a manner that improves with increased operation and observation of user behavior. User behavior and entities (ads, coupons, products) and information (text) are all represented as content vectors in a unified vector space. The system is based on an information representation called content vectors that utilizes a constrained self organization learning technique to learn the relationships between symbols (typically words in unstructured text). Users and entities are each represented as content vectors.