This study examined the association of friendships and popularity with adolescents’ first-time involvement in a romantic relationship (referred to as romantic relationship debut). The aim of this article was twofold: first, to disentangle the unique effects of friendships and perceived popularity; second, to separate same- and cross-gender peer nominations. Specifically, it was tested whether same- and cross-gender friendships or same- and cross-gender popularity were more likely to increase the likelihood of romantic relationship debut. Using longitudinal data of 590 Dutch adolescents age 12 to 18 (57 % girls) from TRAILS (Tracking Adolescents’ Individual Lives Survey), results are consistent with the hypothesis that cross-gender friendships and cross-gender popularity increase the chances of a romantic relationship debut. Findings indicate that peer evaluations by cross-gender peers of both friendships and popularity account for adolescents’ romantic relationship debut.