Background: Strategies to address weight recidivism following Roux-en-Y gastric bypass (RYGB) could be developed if patients at risk were identified in advance. This study aimed to determine factors that predict weight regain. Methods: Retrospective review was performed of patients who underwent laparoscopic RYGB at a single institution over 10 years. Group-based modeling was used to estimate trajectories of weight regain after nadir and stratify patients based on percent weight change (%WC). Results: Three trajectories were identified from 586 patients: 121 had ongoing weight loss, 343 were weight stable, and 122 regained weight. Male sex (p = 0.020) and white race (p < 0.001) were associated with stable weight or weight regain. Being from a neighborhood of socioeconomic advantage (p = 0.035) was associated with weight regain. Patients with weight regain experienced improved percent weight loss (%WL) at nadir (p < 0.001) and ΔBMI (p = 0.002), yet they had higher weight and BMI and lower %WL and ΔBMI than the other two groups during long-term follow-up. On multivariate analyses, those who regained weight were more likely from socioeconomically advantaged neighborhoods (OR 1.82, CI 1.18–2.79). Conclusions: Several patient-related characteristics predicted an increased likelihood of weight regain. Further studies are needed to elucidate how these factors contribute to weight recidivism following bariatric surgery.