The present study investigated developmental differences and stability in possible selves within the educational and occupational domain among a diverse sample of urban youth (N = 319). A secondary aim was to test the "aspiration–expectation gap" while exploring the role of subjective social class and gender differences. Results did not indicate any significant differences among possible selves between different grades in high school. Seniors evidenced the lowest levels of subjective social class, whereas freshmen had the highest levels. Subjective social class was significantly associated with the expected levels of education. In addition, girls aspired toward significantly higher levels of prestige than boys in terms of occupations they hoped to attain, while a substantial gap was found between hoped-for and expected education. Implications for practice, limitations, and directions for research are discussed.