This paper explores the relationship between gender, academic achievement, and family functioning in a Chinese cultural background. Primary and secondary school students (n = 1597) in Hong Kong participated in a survey questionnaire. Two competing hypotheses are derived and empirically tested based on the idea that parents are likely to have higher expectations toward their sons. First, when boys perform well academically, their parents might not feel particularly overjoyed because their sons simply achieved what they were expected to, which would not affect the parents’ attitudes within the family and thus the boys’ perceptions of the family. Second, when parents have such high expectations for their sons, they would feel particularly satisfied when the outcome fulfills their high expectations. The results indicated that boys did well academically to prevent their parents from potential disappointment, whereas parents were actually happier if their daughters overachieve because they have lower initial expectations. Such differences affected parents’ attitudes, family functioning, and thus adolescents’ view of family. The results of this study carry implications for the study of family functioning and parenting among Chinese families. In particular, parents should avoid having gender-based expectations toward their children, which could adversely affect how boys view their family.