The school-to-work transition (STWT) is a pivotal period during which young graduates form the anticipatory psychological contract (APC), encompassing expectations of employer inducements (EEI) and intentions of employee contributions (IEC). Using three-wave data collected to test a reciprocal random-intercept cross-lagged panel model (R-RICLPM), this study investigates the dynamic relationships between these dimensions, along with the role of optimism as an antecedent and its link to person-organization (PO) fit. Our findings reveal significant contemporaneous reciprocal effects between EEI and IEC within each time point, indicating mutual reinforcement. Cross-lagged analyses show an asymmetry, with EEI predicting subsequent IEC but not vice versa. Optimism predicts between-person differences in EEI and IEC, with EEI mediating the relationship between optimism and PO fit. However, IEC negatively associates with PO fit, suggesting potential misalignments. This study advances psychological contract theory by modeling APC dynamics, integrating self-regulation theory, and emphasizing optimism's role in fostering successful STWT outcomes.