Assisting conversation while listening to audio

A portable system for enhancing communication between at least two users in proximity to each other while listening to a common audio source, comprising:

• first and second headsets, each headset comprising:
• an electroacoustic transducer for providing sound to a respective user's ear, and
• a voice microphone for detecting sound of the respective user's voice and providing a microphone input signal;
• and
• a first electronic device integral to the first headset and in communication with the second headset, configured to:
• generate a first side-tone signal based on the microphone input signal from the first headset,
• generate a first voice output signal based on the microphone input signal from the first headset,
• receive a content input signal,
• receive a first far-end voice signal from the second headset,
• combine the first side-tone signal with the content input signal and the first far-end voice signal to generate a first combined output signal, and
• provide the first combined output signal to the first headset for output by the first headset's electroacoustic transducer.