Traditionally, searching in general or querying in particular required the exact matching of value to return results. As technology improves in the information sector, the complexity of these systems also increases. This is fairly common, especially in the area of databases as new models, like XML, are emerging. Searching for information is becoming more challenging for most users as the user population is increasing rapidly to include more less skilled (naive) users. This is especially true when web-based search is considered. Most users are no more familiar with structured languages like SQL and XQuery. Using relative linguistic terms for querying seems to be the most reasonable and logical approach to making any composite resource a more searchable database of information, while implementing fuzziness in XML accounts for the lack of structure that results from pooling databases together. This seems to be the natural evolution of the technology as it moves away from complex and confusing interfaces to more user-friendly, user-centric and intuitive ones. To address these concerns, this chapter describes the design and implementation of a fuzzy nested querying system for XML databases. The research involved is outlined and examined to decide on the most fitting solution that incorporates fuzziness into a user interface intended to be attractive to naive users. After researching the task, we applied our findings via the implementation of a prototype which covers the intended scope of a demonstration of fuzzy nested querying. This prototype has been integrated into VIREX (a user-friendly system that allows users to view and use relational data as XML); the developed prototype includes an easy to use graphical interface that will allow the user to apply fuzziness in order to easier search XML documents. The goal of this is to provide insight on creating more intuitive ways of searching and using XML databases; thus increasing the size of the population using and addressing XML data. We intend to expand into relational and object-oriented databases.