This study tested the situational hypothesis, by examining the perceived availability of three types of social support (emotional, informational, and instrumental) from parents and friends, with respect to occupational and interpersonal relationships issues. Participants were 257 Chinese Singaporean adolescents (120 males, 137 females) between ages 14 and 16. Results showed that males perceived greater parental than friend support, regardless of domains and types of social support. Females perceived greater parental than friend support in the occupational domain, but no significant difference was observed in the interpersonal relationship domain. Females also perceived greater emotional support from friends than parents, but more informational and instrumental support from parents than friends. These findings highlighted contextual and gender differences in the understanding of social support in adolescence. The results were also contrary to predictions according to the situational hypothesis and demonstrated the central influence of parents in the Chinese family, particularly on sons.