Actual-ideal discrepancies are associated with adolescent emotional distress and there is evidence that the size of discrepancies matters. However, the direction of discrepancies has not been examined, perhaps due to limitations of widely used self-discrepancy measures. Two hundred and twelve 7th, 9th and 11th grade students (59% female) in a public school in Jamaica described their actual and ideal selves in several different domains—friendship, dating, schoolwork, family, sports, and religion/spirituality—using a Pie measure. Students also completed measures of depressive symptoms, self-esteem, and academic achievement. Discrepancies favoring the ideal self and those favoring the actual self were linked to depressive symptoms, low self-esteem, and poor school grades in the domains of friendship, dating, and schoolwork. Effects were stronger among older adolescents than among younger adolescents. Theories of actual/ideal self-discrepancies have focused on problems arising when the ideal self overshadows the actual self; however, the present study finds that self-discrepancies, regardless of their direction, are a liability. Implications for self-discrepancy measurement, adolescent development, and clinical practice are discussed.