This study investigated associations between maladaptive ingestive behaviors and weight regain in women who underwent metabolic surgery 2-10 years ago. Using a web-based survey, we assessed emotional, external, and restrained eating (Dutch Eating Behavior Questionnaire-DEBQ), food cravings (Food-Craving Inventory-FCI), and other behaviors (e.g., Eating Disorder Examination Questionnaire-EDE-Q; Alcohol Use Disorder Identification Test-Concise-AUDIT-C) in 36 women (42.9 ± 9.5 years old) post-surgery. We found that weight regain was specifically associated with increased frequency of cravings for sweets (r = 0.43), higher global scores in the EDE-Q (r = 0.38), and time elapsed since surgery (r = 0.35; all p's < 0.04). Multiple regression analysis revealed that the association between weight regain and sweet cravings interacted with time after surgery (p = 0.04), with the strongest association observed in women assessed closer to the surgery (i.e., 2.0-2.8 years). The combination of time after surgery and its interaction with sweet cravings accounted for 31% of the individual variations in weight regain (p = 0.005). Notably, among participants who reported alcohol consumption (31 of 36), 55% had an AUDIT-C score indicating hazardous drinking. These findings highlight the relevance of attending to patients' reports of frequent sweet cravings and screening for alcohol use to enhance strategies tailored to prevent weight regain and alcohol-related health problems post-surgery.