An earphone has a body housing a transducer that is capable of generating an acoustic signal and directing the acoustic signal to an outlet in the body, the body being positionable in, on, or near an ear of user so that the acoustic signal can be directed into the ear canal of the user. The earphone also has an ear coupling mechanism comprising a sealing mechanism with a sealing member that is adapted to contact a portion of the ear of the user to at least partially create a seal between the ear canal and the external environment and a venting mechanism capable of venting air between the ear canal and the external environment, the venting mechanism comprising an air conduit that is adapted to communicate on one end with the ear canal and at another end with the external environment so that air can flow through the conduit to equalize a pressure differential across the sealing mechanism. The air conduit is sized and shaped so as to provide an improved audio performance over an earphone without the air conduit.