The objective of this study was to assess whether body dissatisfaction predicted weight loss in terms of an inverted U relationship. It was predicted that women with high and low body dissatisfaction were less likely to lose weight than women with moderate levels of body dissatisfaction. The study also sought to determine if the number of weight loss attempts, success at past weight loss and self-concept predicted percentage of weight loss in women at six months; and to test whether weight loss led to decreased body dissatisfaction and increased self-concept. Women attempting to lose weight (n = 209) were asked to complete a set of questionnaires at two time points. Results show that women with moderate scores on body dissatisfaction lost more weight than women with higher or lower scores, although this association disappeared when Body Mass Index (BMI) was controlled for in the analyses. Low BMI, success of previous weight loss and low personal self-concept predicted weight loss six months later. Women who lost weight reported lower body dissatisfaction and improved self-concept. It was concluded that, assessing for body dissatisfaction, BMI and weight loss history in the context of primary health settings, may aid in identifying women able to motivate themselves to successfully lose weight in a self-directed manner.