A system and method for organizing information in a personal information space. The personal information space includes at least one data source holding at least a portion of the personal information space. The system includes an agent for the data source which provides interaction information regarding data in the data source; and a interaction evaluation engine including one or more weighting characteristics for each interaction, and providing an output reflecting a weighting of one or more characteristics of the interaction. The method may comprise the steps of determining when an interaction between a contact on one of the contact data sources occurs; analyzing one or more characteristics of the interaction event to determine a at least one trait about the interaction; and generating a result based on said step of analyzing.