Lifestyle and health-related quality of life (HRQoL) are good markers of surgical obesity treatment. This study aimed to investigate the lifestyle and HRQoL of patients at least five years after Roux-en-Y gastric bypass in public (SUS) and private (PVT) Brazilian healthcare systems. In this cross-sectional study, weight loss (WL), % of excess WL (%EWL), diet quality, physical activity, alcohol consumption, and HRQoL were evaluated. Analysis of covariance, binary and multinomial logistic regression, adjusted for confounders, were performed. The SUS group had more vulnerable socioeconomic statuses than the PVT group. Total %WL and % EWL were 24.64 ± 0.99% and 60.46 ± 2.41%, respectively, without difference between groups. In the Pain/Discomfort and Anxiety/Depression domains of HRQoL, more than 50% reported moderate problems without differences between groups. Processed food ingestion was higher in the PVT (132.10 ± 60.15 g/1000 kcal) than in the SUS (103.43 ± 41.72 g/1000 kcal), however, without statistical significance (p = 0.093). The PVT group showed lower physical activity (OR: 0.23; 95%CI: 0.87–0.63; p = 0.004) and a higher risk of alcohol-related problems (OR: 3.23; 95%CI; 1.03–10.10; p = 0.044) compared to SUS group. Participants generally achieved satisfactory WL, regardless of healthcare systems. However, PVT participants had unfavorable lifestyle characteristics, highlighting the need for studies investigating environmental issues post-bariatric surgery.