Medicalised concerns about an obesity crisis persist yet more needs to be learnt about everyday orientations to weight (loss). This article reports and analyses data generated using qualitative methods, including repeated interviews and fieldwork conducted over one year in Canada with women (n = 13) identifying as (formerly) obese. Three ideal types are explored using empirical data: (1) hopeful narratives; (2) disordered eating distress; and (3) weight‐cycling or stagnation. Core themes include women's desire to embody a thin(ner) future and the good life, the harms of intentional weight‐loss, and resignation to living as a fat woman whilst nonetheless challenging stigma. The article contributes to critical studies of weight/fatness, the sociology of bodily change and the embodiment of health identities. In concluding, we call for reflexive change in bodies of health knowledge, policy and practice.