The relationship between eating behaviors, food intake, and mental health and the occurrence of obesity in older adults has rarely been investigated. Therefore, the objective of this study was to establish the associative links of these factors with two measures of obesity: class I obesity as indicated by body mass index (OB-BMI; BMI ≥ 30kg/m2) and class I obesity as indicated by waist circumference (OB-WC; WC ≥ 43 inches for men and ≥ 42 inches for women). Older adults participating in the Older American’s Act (OAA) congregate meal program (N = 113, mean age = 74 years, 74% female, 45% African American) were assessed. Eating behaviors (cognitive restraint, uncontrolled eating, and emotional eating), food groups group choices (sweets, salty snacks, and fruits), and mental health indices (depression, anxiety, and stress) were recorded by questionnaire and related to measured occurrence of OB-BMI and OB-WC. In a series of multivariate logistical regression models, we found cognitive restraint to be consistently and robustly associated with both measures of obesity. In the fully adjusted model, cognitive restraint, consumption of sweets, anxiety, and lack of depression were associated with OB-WC. In summary, we found an association of obesity with abnormal eating behaviors, certain food group intakes, and mental health symptoms in this population. These findings may guide the development of future weight management interventions in a congregate meal setting.