Background: Bariatric surgery requires long-term changes in eating behavior. Bariatric patients can experience difficulties adhering to postsurgical dietary guidelines. Long-term data are scarce. Methods: Individuals (N = 101) who had undergone bariatric surgery (mean 4.6 years ago) completed a survey collecting data on weight, changes in eating patterns, compensatory behavior, and compliance with postsurgical dietary guidelines. The associations between healthy and unhealthy behaviors, weight loss, and patient satisfaction were analyzed. Results: A substantial number of patients mentioned nonadherence to the guidelines. In particular, postoperative restrained eating, nonvitamin use, and excessive exercise more than three times per week. These behaviors were associated with less weight loss, but only the association with postoperative restrained eating was statistically significant. In addition, reporting of unhealthy behaviors was associated with less satisfaction with respect to the bariatric surgery trajectory. Conclusion: Adherence to postoperative behavioral guidelines remains essential at follow-up ∼5 years after bariatric surgery and should remain a focus of clinical follow-up to prevent negative impacts on weight, health, and satisfaction with the trajectory after bariatric surgery. The present results need to be replicated, and more research is necessary to unravel the effect of unhealthy behaviors on long-term outcomes following bariatric surgery.