Long-term results of dietary weight loss interventions are not promising, with rates of weight loss maintenance at a mere 20%. Psychological factors related to weight maintenance include setting unrealistic weight goals, poor problem-solving skills, low self-efficacy, dichotomous thinking, and external locus of control. The ability to maintain a stable bodyweight over time has been associated with optimal health outcomes, lower stress levels, and higher general well-being. Dichotomous thinking has been associated with overeating and increased bodyweight. Cognitive restraint, disinhibition, and hunger are three dimensions of human eating behavior that appear to be important to understanding weight loss maintenance. Individuals who attempt to maintain their bodyweight via dietary restraint mechanisms are more susceptible to excessive eating episodes. Disinhibition has been found to be the strongest predictor of weight gain, while the research on the association between hunger and bodyweight is mixed. This study sought to evaluate the relationship between dichotomous thinking toward food and various eating behaviors (binge eating, cognitive restraint, disinhibition, and hunger). A multiple regression analysis revealed that binge eating, cognitive restraint, disinhibition, and hunger were each significant unique predictors of higher body mass index (BMI). Higher levels of hunger predicted lower BMI, controlling for cognitive restraint, disinhibition, and binge eating. Mediation analyses revealed that dichotomous thinking mediated the relationships between binge eating and BMI, cognitive restraint and BMI, and disinhibition and BMI. Further analysis revealed that binge eating mediated the relationship between dichotomous thinking and BMI, indicating that thinking of food in black-and-white could lead to higher rates of binge eating, and the excess calorie consumption could lead to increased BMI. The study findings suggest that a strong focus should be made to promote a more flexible attitude toward food in an effort to improve weight loss maintenance in the population.