Expecting to become pregnant or to get someone pregnant in the near future separates adolescents in terms of both their current circumstances and future experiences. Drawing on life course, social control, and reasoned action perspectives, this study examined the predictors and outcomes of adolescents’ pregnancy expectations in the National Longitudinal Survey of Youth 1997, emphasizing non-linearity in the meaning and implications of such expectations during a critical period when youths’ future plans begin to change from hypothetical ideas to actual realities. The results suggested that the number and type of risky behaviors during adolescence were associated with an increased level of pregnancy expectations that, in turn, predicted later childbearing. Importantly, risky behaviors also moderated the link between pregnancy expectations in adolescence and fertility in young adulthood, with childbearing more likely to follow split expectations when youth also engaged in risky behavior. These patterns did not vary substantially by gender. / text