There is provided an information processing device including a request transmitting portion that transmits a request, a response receiving portion that receives a response corresponding to the request, a response analyzing portion that analyzes the response, a text output portion that outputs, to the user, text generated based on the response analysis result, a request generating portion that newly generates the request based on the response analysis result or text input by the user, and a timing control portion that controls a timing at which the request is newly generated based on a timing at which the generated text is output.