recipients for the passed along content and thereby predict what advertising messages might be most effective these artificial intelligence methods include algorithms that look for the frequency of keywords to help determine the context of the content as well as categories of content such as business entertainment technical etc and other taxonomies and classifications by having a database with records about the sender and or intended recipients and understanding the relationship between them the invented system can make an intelligent guess about what advertising messages may interest the sender and or the recipients the fields that are stored about the sender and recipient may include but are not limited to first name and last name company name title or role address city state zip phone number e mail address personal or company website address demographics data such as male female age income level education level hobbies etc history of content passed along to others ads acted upon etc by examining this and other information surrounding the content whether hidden or not hidden the invented system can further deduce what advertisements would be more appropriate than other advertisements given the available inventory to insert along with the passed along content the fields that are stored in the content metadata database may include but are not limited to content title content description or summary content author story id tags inserted by publishers and their content management systems to provide information to search engines and other tools about the story so it can be found and categorized content category i e classifieds business features archives etc advertising tags.