[Object] To provide an information processing system and an information processing method to enable an automatic response to be performed with higher affinity in accordance with a mental condition of a user.[Solution] An information processing system including: a database that accumulates a relationship between a user for which a virtual agent is substituted and a partner user as a communication partner on a network; and a control unit that generates a message in accordance with a mental condition of the partner user and the relationship between the user and the partner user, and sends the message from the virtual agent to the partner user.