This study examined how gender, instrumentality, expressivity and dating status were associated with adolescents' perceived cross-sex friendship quality. Two hundred sixty-two Hong Kong Chinese heterosexual teenagers (117 males, 145 females) aged 14 to 18 rated the levels of companionship, closeness, help, security and conflict in their best cross-sex friendships. Results showed that girls perceived more help but also more conflicts. Instrumentality and expressivity were consistent correlates of closeness and security, but they predicted other features differently in the two genders. Daters reported higher levels of companionship, closeness and help. Dating girls, in particular, perceived these friendships as involving the highest levels of security. These results provide some support for social role theory and interdependency across adolescents' social relationships. [Copyright of Sex Roles is the property of Springer New York LLC. Full article may be available at the publisher's website: http://dx.doi.org/10.1007/s11199-010-9880-5 ]