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This study explored experiences with time-restricted eating (TRE) and weight loss in the RESET trial, including 3 months of intervention and 3 months of follow-up. Participants were living with overweight and at risk for type 2 diabetes (T2D). Data included semi-structured interviews and body weight measurements at baseline, post-intervention and follow-up. Participants were grouped based on relative weight loss: (1) High weight loss (median −5.1% (range: −2.4% to −7.1%)) (n = 6), (2) moderate weight loss (median −1.1% (−1.4% to −0.7%)) (n = 7) and (3) low/no weight loss (median +0.8% (range: −0.2% to +3.4%)) (n = 7). Second, interviews were analysed longitudinally, applying content analysis. The concept of career was used to analyse TRE preparation, initiation, continuation and maintenance. Participants who achieved high weight loss when practicing TRE had structured daily routines, consistent meal patterns and strong social support from partners. They adapted quickly to TRE and maintained/furthered their weight loss during follow-up. Although weight loss was an initial motivator for all, participants motivated by health benefits found TRE easier and achieved better weight loss results than those overly focused on losing weight. Participants who achieved moderate weight loss faced TRE challenges due to inconsistent routines and motivations, often switching to ‘traditional dieting’ during follow-up. Participants who achieved low or no weight loss struggled with irregular routines, low social support, guilt when exceeding the eating window and viewing weight loss as an all-or-nothing goal of TRE, making it unmaintainable. In conclusion, successful TRE practice for weight loss requires greater flexibility in the concept, tailored guidance to adapt daily routines and strengthening social support.