An input unit supplies a logic operation expression made up of a plurality of retrieval keys and logic operators between the retrieval keys, entered by the user, to a control unit. A similarity calculating unit calculates similarities between key contents designated by the retrieval keys and a plurality of retrievable contents, based on feature quantities of contents that are supplied from a feature quantity extraction unit and a feature quantity database. A combining unit performs logic operations using the similarities between the key contents and the retrievable contents, calculating combined scores for the respective retrievable contents. The retrievable contents which have large combined scores are presented as contents best suited to the user. The present invention is applicable to an information processing apparatus for retrieving contents, for example.