A shopping server proposal system includes a mechanism that enhances the online retailer's existing database system with the necessary information to provide the desired services. The existing catalog of items is analyzed based on a set of predefined rules for a given retail store. This analysis determines which of the items in the catalog are related to other items in the catalog. The result of this analysis includes new relations of the catalog items that are written into the retailer's existing database system. The mechanism for assembling this information, based on a set of predefined rules, is independent of the retailer or the retailer's industry. The provides retail businesses with a competitive edge by enabling them to offer automated shopping advice to solve the shoppers' problems of finding related and matching items, and by providing a list of related items based on the selected item's properties.