A system and method are provided for enabling a portable media player to obtain media content from secondary systems, such as other portable media players, via local wireless communication. In general, the portable media player stores proxy information identifying the media content of a number of media files in the user's media collection rather than the media files themselves. When a secondary system is within a local wireless coverage area of the portable media player, the proxy information for the media files, or a subset thereof, is provided to the secondary system. In response, the secondary system identifies media files stored by the secondary system having media content matching the media content identified by the proxy information. The secondary system then provides a notification of the identified media files to the portable media player, which may then obtain the identified media files from the secondary system.