In this study we investigated the moral dilemmas and strategies of a group of Danish parents who were trying to help their overweight children lose weight. Data were drawn from repeated semistructured interviews carried out over a period of 2 years with 12 families with overweight children. Using a narrative approach, we show the moral dilemmas parents found themselves in when trying to further the two seemingly incompatible goals of helping their children lose weight and simultaneously strengthening their self-worth. When the children were young, the parents tried to hide the fact that they needed to lose weight to protect them from feeling stigmatized. As the children grew older, the parents became more forthright about weight loss so the children would take on more responsibility. We suggest that for parents, weight loss is experienced as a risky undertaking because they perceive their children’s self-worth as being in jeopardy during the process.