Associations among dating, sexual activity, gender, and adjustment were investigated in 2,273 Italian adolescents (54% female, ages 14 to 19 years) attending public high schools. After controlling for age and type of school attended, both being in a dating relationship and being male were associated with less alienation, more positive views of the self, and higher general expectations for success. Sexual activity interacted with both gender and dating status in predicting feelings of depression. For boys, there were no differences between youth who were sexually active and youth who were not; however, sexually active girls had higher levels of depressive symptoms than girls who were not sexually active. Among youth who were not sexually active, there were small differences between daters and nondaters; among sexually active youth, daters had lower levels of depression than nondaters. Gender differences in adolescents' experience of dating and sexual relationships and implications for adjustment are discussed.