There is provided an information processing apparatus for automatically generating information representing a context surrounding a user, the information processing apparatus including: a recognition processing unit configured to perform, on the basis of user environment information including at feast any of location information representing a location where a user is present, image information relating to an environment surrounding a user, and audio information relating to the environment, an analysis process of at least any of the location information, the image information, and the audio information included in the user environment information, at a predetermined time interval, and to recognize a context surrounding the user, using the acquired result of analysis relating to the user environment; and a context candidate information generating unit configured to generate context candidate information representing a candidate of the context surrounding the user, the context candidate information including, at least, information representing the context surrounding the user and information representing the user's emotion in the context using the result of context recognition performed by the recognition processing unit.