In order to examine the association between sexual behavior and depressive affect among adolescents, 122 and 219 Israeli adolescents, in two separate studies, reported their romantic and sexual history, the quality of their relationships and level of depressive symptoms. Findings show that a higher level of sexual activity in short-term romantic relationships, which were low in intimacy and authenticity, was related to increased levels of depressive symptoms among females but not among males. In contrast, involvement in stable romantic relationships was not associated with increased depressive affect for either gender. Findings from a 3 month follow-up suggested that it may be that an increased level of depressive symptoms leads adolescent females to become more sexually involved in short romantic encounters.