Provided is an information processing system including a position management unit configured to manage positions of avatars operated by users in a virtual space, a schedule management unit configured to manage a schedule of communication of the users, and a control unit configured to cause communication between terminals used by the users who are scheduled to have the communication to be established when the avatars of the users who are scheduled to have the communication gather in a predefined place in the virtual space and to cause at least one of an image and a voice to be transmitted and received.