Disclosed is an information processing apparatus including: a learning unit that learns user preference for each type in each category for classifying content items in a server; a selection unit that, based on type information indicating a recommendable type which is a type of content items recommendable by the server and a substitutable type which is a type that satisfies a predetermined condition out of the recommendable type, selects one or more recommendable types in a case where there is the recommendable type corresponding with user preference in the selected category, and selects one or more substitutable types in the selected category in a case where there is no recommendable type corresponding with user preference; and an obtaining unit that obtains a content of the selected type from the server.