A proximity sensing headphone may include a gyroscopic sensor to determine the motion of the headphone structure and a proximity sensor to determine the movement of an external object through a three-dimensional ambient environment. A proximity sensing headphone control circuit determines the relative motion or movement between the headphone structure in the three-dimensional ambient environment and the external object in the three-dimensional ambient environment to determine at least a distance between the headphone structure and the external object and a velocity of the external object through the three-dimensional ambient environment about the headphone structure. The control circuit may provide an alert output if the determined distance between the headphone structure and the external object is less than a defined distance threshold or the velocity of the external object through the three-dimensional ambient environment about the headphone structure exceeds a defined velocity threshold.