A digital audio system configured to facilitate a collaborative audio session comprises a first digital audio device operable by a first user, a second digital audio device operable by a second user independently of the first digital audio device, and a server configured to communicate with the first digital audio device and the second digital audio device over a network, receive a request from at least one of the digital audio devices for participation in a collaborative audio session, and facilitate communication between the first digital audio device and the second digital audio device.