This research takes a new look at individuals' attitudes and intentions towards losing weight. Study 1 examines the relationship among those interested in losing weight and individual self-evaluative ambivalence on attitude towards trying to achieve a weight loss goal and the intentions to achieve the weight loss goal. For Study 2, a between-subjects experimental design, where attitudinal ambivalence and prior outcome feedback were manipulated and self-efficacy was measured, is conducted to examine attitude towards eating healthier and intention to change eating behaviours. Findings across the two studies show that attitudinal ambivalence about the self and the individual's abilities and motivation to change the health behaviour produces a negative relationship between health-related attitudes and intentions. We provide implications of how self-efficacy and the provision of outcome feedback can alleviate the negative effect and improve the individuals' intentions to try to achieve a weight loss goal.