Using data from Waves I and III of Add Health, this study examines early family formation among 6,144 White, Black, and Mexican American women. Drawing on cultural and structural perspectives, models of the first and second family transitions (cohabitation, marriage, or childbearing) are estimated using discrete-time multinomial logistic regression. Complex differences by race and ethnicity and generation are partially explained by differences in attitudes and values in adolescence and family socioeconomic status; marriage values are especially important in first-generation Mexican women's early entry into marriage. Examination of sequential family transitions sheds light on racial and ethnic differences in the meaning and consequences of early cohabitation and pre-union births. (Contains 2 notes and 4 tables.)