Systems and methods for detecting proximity of a wireless listening device to a user's ear comprise a housing adapted for positioning in and/or adjacent to an ear canal of a user, wireless components disposed within the housing, the wireless components operable to receive a wireless signal from a host device, and in-ear detection components operable to analyze the wireless signal and detect a proximity of the housing to the ear canal of the user. The in-ear detection components may include a differentiator operable to receive a gain of the wireless signal and output a rate of change of the gain, a comparator operable to output a proximity state if the rate of change is greater than a threshold value, wherein the proximity state includes an in-ear state and an open-air state, and false detection components operable to analyze the wireless signal to confirm the determined proximity state for an interval of time.