A method of selecting and presenting content based on context-sensitive learned user preferences is provided. The method includes providing a set of content items having descriptive terms. The method includes receiving user input for identifying items and, in response thereto, presenting a subset of items. The method includes receiving user selections of said items and analyzing the descriptive terms of those items to learn the user's content preferences. The method includes determining the context in which the user performed the selections and associating those contexts with the user content preferences learned from the corresponding user selections. The method includes, in response to subsequent user input, determining a context of said subsequent input and selecting and ordering a collection of items based on comparing those items' descriptive terms with the user's learned content preferences associated with the determined context in which the user entered the subsequent input.