Though most extant research suggests that educational expectations are adopted early in life and stabilize by adolescence, recent research has begun to challenge this assumption. This study further examines whether and to what degree adolescents' educational expectations adapt in response to two mechanisms: interpersonal influence and self-reflection. Because educational expectations correlate with gender disparities in academic achievement, this study also examines whether this developmental trajectory varies between boys and girls. Results from a series of path models indicate that educational expectations do adapt, but any meaningful adaptation requires unrealistically large changes in academic performance. Additionally, results show that boys adapt their educational expectations in response to their academic performance more so than girls. These results are discussed in light of current policy efforts that seek to increase educational attainment through adolescents' educational expectations.