Background: Among the dysfunctional eating behaviors associated with excessive food intake, a construct that is gaining increasing attention is grazing—the constant, continuous, compulsive, and repetitive consumption of small/moderate amounts of food. Furthermore, in some cases, grazing seems to indicate a dependence on food and/or eating. Currently, the Repetitive Eating Questionnaire (Rep(Eat)-Q) appears to be the only questionnaire that comprehensively measures grazing, including its repetitive and compulsive eating component. Therefore, in a sample of individuals with severe obesity, the objective of this study was twofold: (A) to evaluate the psychometric properties of the Italian version of the Rep(Eat)-Q, and (B) to analyze the association between grazing and food addiction (FA). Method: A cross-sectional research design was used. A total of 402 inpatients with severe obesity (BMI > 35) were recruited. Participants underwent a series of questionnaires to investigate structural validity and convergent validity and association with FA criteria. Results: The factorial structure of the Rep(Eat)-Q is robust and showed fit indexes: CFI = 0.973; RMSEA = 0.074; 90%CI [0.056–0.091]; and SRMR = 0.029. Also, it exhibited good internal consistency and convergent validity. Furthermore, logistic regression analysis highlights a specific association between certain FA criteria and grazing. Conclusions: The Rep(Eat)-Q can be considered to be a concise, robust, reliable, and statistically sound tool to assess repetitive eating, specifically grazing. Its strong psychometric properties offer significant advantages for both research and clinical applications. Furthermore, in a sample of individuals with severe obesity, the results suggest that individuals with problematic grazing exhibit a typical behavioral profile of subjects with FA, indicating that FA can manifest through problematic grazing as well.