Information processing system and information processing method

An information processing system includes a storing unit that stores evaluation data in which a plurality of subjects are associated with a plurality of evaluation expressions respectively and evaluation expression relationship data indicating relationships between the evaluation expressions, a question generating unit that generates and outputs questions on the basis of the evaluation data and the evaluation expression relationship data, and a matching unit that outputs information relating to the subject included in the evaluation data on the basis of responses when the responses with respect to the questions are input.