IntroductionPrevious weight loss attempts in young people with obesity may have influenced their beliefs about themselves and contributed to maladaptive eating behaviors. Therefore, we aimed to investigate the association between previous weight loss with self-esteem and different eating behaviors in adolescents and young adults with obesity seeking specialty obesity care.MethodsWe performed a cross-sectional study, where a total of 224 participants with obesity, aged 16–25, self-reported the amount and the frequency of previous weight loss of 5 kg or more. Self-esteem was assessed with Rosenberg's Self-Esteem Scale and eating behavior with the Three-Factor Eating Questionnaire-Revised21. Linear regression was used to analyze associations between the amount of weight loss (no weight loss, 5–10 kg, and >10 kg) and the frequency of weight loss ≥5 kg (0, 1, and ≥2 times) with self-esteem and eating behaviors.ResultsWe found that both those who had lost 5–10 kg and those who had lost ≥5 kg twice or more, had statistically significantly higher cognitive restraint eating scores β = 7.03 (95% CI: 0.004–14.05) and β = 8.32 (95% CI: 1.20–15.43), respectively, compared to those who reported no previous weight loss. No other statistically significant associations were found.ConclusionPrevious weight loss in adolescents and young adults with obesity may be associated with a higher cognitive restraint eating behavior. Therefore, assessing weight loss history and eating behavior may be beneficial to better individualize obesity treatment.