To examine associations between participation in Tulsa's preschool programs and a set of middle-school attitudes, we used propensity score weighting to compare the Tulsa Public Schools (TPS) pre-K participants and, separately, the Community Action Project (CAP) Head Start participants to students who had attended neither TPS pre-K nor Head Start as 4-year olds. In the context of very few significant findings, positive associations were found between pre-K participation (in both the TPS pre-K and CAP Head Start programs) and the students' attitudes about grit as assessed with the goal-setting subscale. Head Start participation was also associated with more cautionary views of risky sexual behavior. The results are discussed with regard to prevailing hypotheses guiding research on long-term pre-K impacts, measurement challenges, and expectations of pre-K education.