Energy balance is one component of weight management, but passive objective measures of caloric intake are nonexistent. Given recent success of actigraphy as a passive objective measure of the physical activity construct that relieves participants of the burden of biased self-report, researchers are aiming to find a passive objective measure of caloric intake to improve understanding of problematic eating behaviors in participants with and without obesity. Passive sensing food intake systems have failed to go beyond the lab and into behavioral research in part due to low adherence to wearing passive monitoring systems. This paper presents preliminary results in participants with and without obesity performing structured and unstructured eating experiments to understand wearable adherence as affected by: 1) perceived data privacy; 2) stigma of wearing devices; 3) comfort. Wearables examined include neck- and wrist-worn sensors, and video camera-based systems.