A calendar-based interface system accommodates innate human memory by associating computer-related events, and other events, based upon when they occur. The calendar user interface system utilizes a calendar as a top-level user interface for accessing computer information. The calendar-based interface system utilizes system-wide monitoring of the user and associations between various computer files, people, and other information related to the user. This allows a user to view and assign searchable metadata (e.g., metadata relating to associated dates) and to retrieve computer information that matches selected metadata.