The invention provides a system and method for defining a schema and sending a query to a Similarity Search Engine to determine a quantitative assessment of the similarity of attributes between an anchor record and one or more target records. The Similarity Search Engine makes a similarity assessment in a single pass through the target records having multiple relationship characteristics. The Similarity Search Engine is a server configuration that comprises a Gateway for command and response routing, a Virtual Document Manager for document generation, a Search Manager for document scoring, and an Relational Database Management System for providing data persistence, data retrieval and access to User Defined Functions. The Similarity Search Engine uses a unique command syntax based on the Extensible Markup Language to implement functions necessary for similarity searching and scoring.