A personal media device transmits media content to one or more nearby personal media devices so that users can dynamically and easily share content. The method includes, on a first media player device having or having access to selected media content, playing the selected media content such that it can be listened to on a first user's headphones. The selected media content is also transmitted such that it can be received and simultaneously played by one or more authorized media player devices associated with additional users. The transmitted content is preferable secure so that only authorized users can access it. The media player devices receiving the transmitted content can be wireless headsets configured to receive and simultaneously play the content.