Objectives. The present study examined correlates of frequent dieting in 33 393 adolescents. It was hypothesized that frequent dieting would be correlated with negative psychosocial and health behavior outcomes. Methods. A comprehensive, school-based health behavior survey was administered in 1987 to public school students in grades 7 through 12 in Minnesota. Students self- reported dieting behavior; substance use; suicidal, sexual, and delinquent behavior; family and peer concerns, sick days; and abuse history. Differences on psychosocial and health behavior risk factors by dieting frequency and by purging status were assessed with multivariate logistic regression, with body mass index and demographic variables controlled. Results. Dieting frequency was associated with history of binge eating (females: odds ratio [OR] = 1.46, males: OR = 1.53); poor body image (females: OR = 0.56, males: OR = 0.63); lower connectedness to others (females: OR = 0.79); greater alcohol use (females: OR = 1.17); and greater tobacco use (females: OR = 1.08). Purging status was independently associated with negative risk factors in both males and females. Conclusions. These findings suggest that frequent dieting efforts in adolescents should not be viewed in isolation, but rather in the broader context of health and risk-taking behaviors.