Although past research indicates that early and premarital childbearing negatively affect mental health, little is known about the role of individual expectations in shaping these associations. Using data from the National Longitudinal Survey of Youth 1979, we consider how individual expectations, measured prior to the entry into parenthood, shape mental health outcomes associated with premarital childbearing and birth timing, and consider gender and race/ethnic variations. Results indicate that expecting children before marriage ameliorates the negative mental health consequences of premarital first births and that subsequently deviating from expected birth timing, either early or late, results in increased distress at all birth ages. In both cases, however, the degree and manner in which expectations matter differ by gender and race/ethnicity. Results indicate that expectations for premarital childbearing matter only for African-Americans’ mental health and although later than expected births are associated with decreased mental health for all groups, earlier than expected births are only associated with decreased mental health for women, Hispanics, and non-Hispanic whites.