In this longitudinal study, reciprocal relations between problematic romantic relationships, depression and anxiety, during the transition to adulthood, in young men and women were examined. Data were collected from high school students in Hawaii, 6 months-2.5 years after high school graduation. The sample was comprised of 382 participants (64% female and 36% male), with a mean age of 18.5 years at Time 4 and 20.5 years at Time 6. The sample was diverse in terms of demographic characteristics. Measures included, the Beck Anxiety Inventory, Center for Epidemiological Studies Depression Scale, and Life Events Inventory. In general our findings suggest that problematic romantic relationships had effects on subsequent depression and anxiety, when controlling for baseline levels. Generally, depression was not a significant predictor of subsequent problematic relationships, however anxiety was. The findings suggest that the effects of problematic romantic relationships were stronger and longer lasting for women than men.