Purpose Home lockdown and isolation due to COVID-19 have been related to negative changes in mood, sleep, and eating behaviors. People with obesity are especially vulnerable to emotional eating and might be more prone to weight gain and negative outcomes during lockdown. Materials and Methods Individuals scheduled for an appointment at the Obesity Unit of a Tertiary Hospital between March 16 and June 21 ( n =1230). An online survey was distributed on May 11. Multivariable logistic regression models and general linear models were used to assess the relationship between perceived COVID-19 threat, BS status, and outcome variables. Results Of the 603 (72.0% females, 39% aged >55 years) respondents, 223 (36.9%) were BS naïve (non-BS), 134 (22.2%) underwent BS within the two previous years (BS<2y), and 245 (40.6%) more than 2 years before (BS>2y). Participants worried about being infected by COVID-19 showed significantly larger changes in family contact ( p =0.04), mood ( p <0.01), sleep ( p <0.01), dietary habits ( p =0.05), purchases of unhealthy food ( p =0.02), snacking ( p =0.05), and physical activity ( p =0.02). Non-BS and BS>2y participants reported greater impact of lockdown in mood ( p <0.01), experienced more negative changes in dietary habits ( p <0.01), and had a higher likelihood for weight gain (OR: 5.61, 95% CI: 3.0–10.46; OR: 5.45, 95% CI: 2.87–10.35, respectively) compared to BS<2y. Conclusions COVID-19 pandemic is having a substantial negative impact in our population affected by obesity. During lockdown, people more than 2 years before BS behave like people without history of BS. Strategies addressed to prevent negative metabolic outcomes in this population are urgently needed. Supplementary Information The online version contains supplementary material available at 10.1007/s11695-021-05225-z.