A System and Method to Deter Obsessive Compulsive Behavior by generating alerts when a users hands are held close to their head or face. The system includes a sensor and a triggering device that are both worn by the user. The sensor can be configured to detect when the triggering device closes to within some threshold distance. The sensor and triggering device may be contained within common personal items, such as jewelry—including rings, bracelets, hair clips, necklaces and the like. The system and method can generate audible and/or visual alerts whenever one or more triggering devices passes closer to the sensor than the threshold distance. Alerts are in a variety of tones, including simulated cellular telephone ring tones. Data for alert events is downloadable from the sensor device for later review.