Gifted girls and women seem to face common barriers to achievement that include feelings of self-doubt, pressure to conform, undemanding school curriculum, unrealistic expectations and a lack of career planning. This study provided an Asian perspective on gifted gifted girls’ psychological adjustment by investigating patterns of well-being in a sample of gifted adolescent girls ages12-16 in Singapore. Patterns in self-esteem, optimism and academic achievement were investigated in a sample of 401 gifted adolescent girls who were enrolled in a single-sex school for the gifted. Self-esteem was measured using the Coopersmith Self-Esteem Inventory while optimism was measured using The Youth Life Orientation Test (YLOT). Results indicated variations in developmental were trajectories. Contrary to research findings in western studies, self-esteem remained quite consistent across grade 7 to 10. Significant upward trends were observed in the General Self and Social Self-Peers subscales of the CSEI.Contrary to research in Asian studies, the girls were significantly more optimistic than pessimistic. The findings also indicated that Total Self-Esteem and optimism predicted academic achievement and that optimism was not a mediating factor in this relationship. The findings suggested that the girls experienced good psychological well-being overall. Results may suggest that that there are socio-affective benefits in grouping gifted girls in an all-girls’ educational environment that serves to cater to their gifts and talents. We discuss the role of educational, cultural and social contexts in the development of gifted adolescent girls.