A system including a first mobile device and a second mobile device is disclosed. The first mobile device has a first interactive pairing criterion associated therewith, and the second mobile device has a second interactive pairing criterion associated therewith. The first mobile device includes a processor configured to perform and/or initiate the following. Upon the second mobile device being geographically positioned within a predetermined geographic distance from the first mobile device, an automatic query is issued to determine whether the first interactive pairing criterion and the second interactive pairing criterion at least partially coincide with one another. Upon a determination that the first interactive pairing criterion and the second interactive pairing criterion at least partially coincide with one another, a digital media file associated with the second mobile device is downloaded.