This study examined the clinical significance of self-reported frequency of time spent dieting in obese patients with binge eating disorder (BED). A total of 207 treatment-seeking obese BED patients (57 men and 150 women) were dichotomized by dieting frequency and gender and compared on a number of historical, psychological, and metabolic variables. Frequent dieters reported significantly earlier age of onset for binge eating, dieting, and obesity, more episodes of weight cycling, greater weight suppression, and greater eating disorder pathology than infrequent dieters; no differences, however, emerged on current binge eating frequency or psychological distress. Among women but not among men, frequent dieters had consistently lower chances of abnormalities in total cholesterol, high-density lipoprotein (HDL) cholesterol, and the total/HDL cholesterol ratio while infrequent dieters had greater chances of abnormalities on these variables. Dietary restraint was inversely correlated with abnormalities in triglycerides, HDL cholesterol, and the total/HDL cholesterol ratio but was unrelated to low-density lipoprotein (LDL) cholesterol. In summary, frequent dieters of both genders had greater lifetime and current eating and weight concerns, and in women, decreased chance of metabolic abnormalities than infrequent dieters. Our findings suggest that frequent dieting attempts, particularly in women, are associated with greater eating disorder pathology but may have a beneficial effect on metabolic functioning and cardiovascular disease risk independent of actual weight status. These findings may have implications for clinical advice provided to obese BED patients.