An information processing apparatus connectable with a user terminal via a network, includes circuitry configured to acquire information input to the user terminal by a user; search response information to be responded to the input information; respond, to the user terminal, a response message based on the response information to the input information; set a plurality of modes each used for performing a dialogue with the user terminal; and store history information of the dialogue that is performed with the user terminal using each of the plurality of modes in a memory.