Systems and methods of desensitizing an animal to an anxiety inducing event, including an output unit to communicate with a media player to output a conditioning media signal and an anxiety inducing media signal, a conditioning element dispenser to dispense a conditioning element, a detector to determine when an animal has taken the conditioning element, and a control module to selectively control operation of the output unit and the conditioning element dispenser to cause the conditioning element dispenser to dispense a first conditioning element in association with the media player outputting the conditioning media signal. The output unit can cause the media player to output the anxiety inducing media signal in association with the conditioning media signal, and the control unit can cause the conditioning element dispenser to dispense a second conditioning element from the conditioning element dispenser in association with the anxiety inducing media signal.