The present invention relates to an information processing system, an information processing apparatus and method, and a program in which the purchase of content can be facilitated. When giving content data as a present, a sender giving the content data sends first information for identifying the sender, second information for identifying the destination of the present, and third information for determining the content data to be given. Then, mail querying whether to accept the content data as a present is delivered to the destination of the present based on the second information. Then, only when a response indicating that the content data is to be accepted as a present is returned in response to the mail, the processing concerning the present is executed. The present invention is applicable to a server for executing processing concerning content data.