There is provided an information processing system including an identifying unit that identifies a user and a target with whom the user requests to converse based on a signal detected by a first sensor arranged around the user, a signal processing unit that performs predetermined signal processing on signals detected by the first sensor and a second sensor arranged around the target, an output control unit that causes the signal detected by at least the second sensor and processed by the signal processing unit to be output to a first output unit arranged around the user, and a recognizing unit that recognizes, when a plurality of the targets are identified by the identifying unit, a selection request for selecting a specific target from among the plurality of targets based on the signal detected by the first sensor.