Although developmental theory predicts that adolescent romantic relationships have important benefits, empirical evidence suggests that they may also carry substantial psychosocial risk. This study uses data from 4,948 respondents (50% female) in Wave I and Wave II of the National Longitudinal Study of Adolescent Health to examine the association between involvement with an older romantic partner and depressive symptoms during adolescence. Ordinary least squares regression models compared Wave II depressive symptoms among respondents with older partners (defined as an age difference of 2 or more years) to respondents with same-age or younger partners, controlling for baseline depressive symptoms and sociodemographic characteristics. Ten percent of females and two percent of males reported having an older romantic partner at Wave II. Among females only, involvement with an older romantic partner was associated with a modest but significant increase in depressive symptoms between waves. This association was largely mediated by increases in substance use. Findings suggest that involvement with an older male partner during adolescence may increase the risk of poor emotional outcomes among females.