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In society, overweight women are expected to engage in regular physical activity to lose weight. Paradoxically, they also face numerous barriers throughout their sports socialization. Based on a qualitative study of women who have undergone or are about to undergo bariatric surgery (interviews and virtual ethnography), this paper identifies three biographical moments that contribute to the production of a conflictual relationship with physical activity among overweight women. First, childhood sports socialization is marked by pressure to lose weight and social exclusion in physical education classes. Second, weight-related stigmatization continues to hinder involvement in physical activity in adulthood. Finally, bariatric surgery often prompts the adoption of new sporting habits—structured, self-monitoring practices—which are usually abandoned over time. While some sports socializations are successful, particularly among women who have gained weight as adults, most overweight women find it difficult to engage in regular physical activity on a long-term basis and to derive enjoyment from it.