The present study investigated the mutual interplay of sexual orientation, masculine and feminine gender role orientation, and sociosexual orientation in young women. To ensure cross-sample validity, 323 heterosexual women and 323 lesbian women, ranging in age from 18 to 29 years, were matched for possible confounding variables. Lesbian women scored significantly higher (d = 0.27) on the Desire subscale of the Revised Sociosexual Orientation Inventory, but not on the Behavior (d = 0.07) and Attitude subscales (d = 0.11). Concerning gender role orientation, heterosexual women were characterized by significantly higher scores on the Femininity scale (d = 0.20), whereas lesbian women showed more pronounced masculine gender role orientation (d = 0.16). Structural equation modeling revealed two functionally distinct relationships between sexual orientation and sociosexuality, on the one hand, and between gender role orientation and sociosexuality, on the other hand. Sociosexual desire was exclusively associated with a woman's sexual orientation with no indication of any mediating effect of gender role orientation. Sociosexual behavior was positively related to a woman's level of masculine gender role orientation, while sociosexual attitude was positively associated with masculine and negatively associated with feminine gender role orientation, irrespective of sexual orientation.