Abstract: A system and method are described for offering items and services for sale that are related to content being displayed in an interactive medium such as the world wide web, public kiosks, hand-held PDAs, tablets, television and other digital devices. The system uses a combination of techniques to select from a catalog of items those which have the greatest relevance to the content being viewed at the time, and it presents those items concurrently in point-of-sale window, allowing the user to purchase the items directly without leaving the content page. Unlike content-sensitive advertising which presents ads even when the relevance of those ads to the content is low, the system alerts the user to the presence of relevant products, presents a point of sale window only if the user requests it, and pays the content publisher a portion of the revenue from sales initiated on his content page.