This invention relates generally to systems and methods for delivering products-on-demand to individuals and, more particularly, to delivery via vending machines. In accordance with a preferred embodiment, the method of the instant invention is initiated when a customer makes an initial product selection. Based the customer's product choice, a determination is made as to whether or not that product qualifies for an alternate product offer. If it does not so qualify, the customer's original selection will be dispensed and the transaction ends. On the other hand, if the product does so qualify, the customer will be presented with an offer message that suggests that he or she should try an alternative product. Typically, the product that is offered as an alternative will be the one whose sale is most beneficial to the vending machine operator, e.g., the one yielding the greatest profit. If the customer accepts the alternate offer, the alternate product will be dispensed. However, if the customer declines the alternate product offer, the originally requested item will be vended. The particular circumstances under which an alternate product offer is presented to the customer are quantified by representing them as a collection of rules, the evaluation of which depends preferably on previously collected sales data.