Background: Obesity is a complex disease affecting more than 78 million Americans and increasingly is treated with bariatric surgery. One of the purposes of the present study was to gain an understanding of psychosocial variables and the influence they have on weight regain and post-bariatric follow-up. Materials and methods: The researchers utilized a combined quantitative and qualitative approach to analyze subjective explanations regarding patients' (n = 667) long-term bariatric experiences regarding post-surgery weight regain. A multiple linear regression analysis was conducted with weight regain as the outcome variable. Data from the study were jointly interpreted and discussed. Results: The final set of six predictors produced a statistically significant squared multiple correlation (SMC) of 0.276 (F 6, 593 = 37.612, p < 0.001), with an adjusted SMC of 0.268. The average amount of weight regain can be expected to decrease by approximately four pounds for each increase of one point on adhering to the recommended postoperative diet. Those who have larger differences from their lowest to highest weights can generally expect to regain slightly more weight. Two qualitative themes on weight regain emerged: (1) weight regain after bariatric surgery is likely (n = 129), and (2) bariatric follow-up and support (n = 118). Conclusion: Results reveal psychosocial events influence individuals even by a small weight regain, which may overshadow the benefits of bariatric surgery.