A method and system for obtaining desired times from intended recipients of items is provided. The method provides each recipient with a plurality of time windows that overlap with one another in time from which the recipient may choose a time for delivery of an item and receives choices made by recipients from the plurality of overlapping windows. One aspect of the invention includes applying predetermined parameters to the time windows to determine which time windows to offer to the recipients as available times from which the recipient may choose a time for delivery. Such parameters may include, among others, which time windows have associated with them the least cost of service in making the delivery, whether the cost of delivering within a time window is less than a monetary threshold, and whether a maximum number of orders to be delivered within one time window has been reached.