A system and method for automated selective gift delivery whereby a gift-giver is provided the opportunity to register as a user of the system and with respect to each desired recipient of one or more gifts for one or more events, typically recurring, to provide information to the system about the recipient and the events such that the system may select, or cause to be automatically selected, a gift suitable for the recipient and event based upon the parameters provided by the gift-giver, and cause the gift to be automatically delivered to the recipient without further action or intervention by the gift-giver. Alternative modes of the invention provide for various additional or alternative actions, including providing for: the sending of alternate gifts, which may be pre-selected or selected by the user; for declining to send a gift; and for sending non-recurring gifts.