An executable shopping list (ESL) enables a user browsing an affiliate Web site's Web page to order, with a single action, a bundle of multiple items offered for sale by the affiliate's associated merchant Web site, wherein the bundle is one that is not offered or available for sale as a bundle to on-line visitors who directly access the merchant's Web site server. By selecting a link on the affiliate's Web page, the ESL is executed, thereby automatically loading the bundle of multiple items on that list into a virtual shopping cart at the merchant's Web site on behalf of the user. The virtual shopping cart, filled with the multiple items, is then returned to the user's browser for completion of the checkout procedure by the user. ESLs can be implemented on the affiliate site's side using what is referred to as smart bookmark technology, which records for later playback, the multiple steps required to load each item on the list into a shopping cart at the merchant's Web server. Alternatively, ESLs cam be implemented on the merchant's site side using the merchant's Web server's infrastructure. A discount can be optionally associated with the offer to purchase the multiple items in the bundle. ESLs are also applied to permission marketing where a merchant can bundle a group of items together and electronically offer that bundle to one or more customers who have agreed to receive such merchandising offers.