The present invention provides an automated system to guide people ("users") to help them find and select products, services, or other items, that best meet their needs and preferences. The system obtains information from and about users to assess their needs and preferences. The system dynamically selects those questions to ask that are most likely to help discriminate between items based on information about user preferences and differences between the items, based on information about the user obtained so far. The system scores the available items in terms of how well they match user's needs and preferences and generates lists of recommended items. The system explains its recommendations using lists of pros and cons to help users understand how well the features or attributes of the items do or do not match their expressed needs.