--- - |2+ Objectives We investigate how different types of high school romantic involvement are associated with women's and men's patterns of college enrollment (four‐year college, two‐year college, and no enrollment). Methods We analyze restricted‐access longitudinal data from the National Longitudinal Study of Adolescent to Adult Health (Add Health) using multinomial logistic regression. Results Controlling for baseline educational, romantic, sociodemographic, and family context variables, results show gender‐specific associations between romantic involvement and college enrollment. For women, negative associations between romantic involvement and four‐year enrollment dissipate after accounting for changes in grade point average and educational and marital expectations. However, a negative association between women's casual dating with sex and two‐year enrollment persists, after controlling for these factors. In contrast, casual dating with and without sex is associated with higher likelihood of men's four‐year enrollment accounting for these covariates. Conclusions Our findings provide directions for future research on associations between gender, adolescent romance, and educational transitions. - Social Science Quarterly, Volume 99, Issue 3, Page 1134-1157, September 2018.