The role of social support in weight management is not fully understood, as more support has been linked to both favorable and unfavorable outcomes. We examined social support in relation to weight loss maintenance, comparing between maintainers and regainers of weight loss. The MedWeight study is a Greek registry of people who have intentionally lost ≥10 % of their weight and are either maintaining this loss for over a year (maintainers), or have regained weight (regainers). Demographics and lifestyle habits questionnaires are completed online. Dietary assessment is carried out by two telephone 24 h recalls. Perceived social support was assessed by validated scales examining support from family and friends regarding healthy eating and exercise. 289 maintainers and 122 regainers participated. Regainers received more support compared to maintainers. However, maintainers reported receiving compliments and active participation, whereas regainers receiving verbal instructions and encouragements. Maintainers who received diet support displayed improved dietary intakes, such as lower energy intake; regainers’ diet was unaffected by support. Positive, rather than instructive, support appears beneficial in weight loss maintenance.