This study explored the association between two parental career expectations (reward/prestige and comfort/stability) and career indecisiveness with the moderation of gender in 523 Chinese undergraduates. We found that women undergraduates perceived lower parental reward/prestige and higher comfort/stability expectations than men. Perceived parental comfort/stability expectations on career indecisiveness were significant for men but non-significant for women. Results indicated a three-way interaction among parental expectations of reward/prestige, parental expectations of comfort/stability, and students' gender in the prediction of career indecisiveness. For women, perceived parental comfort/stability and reward/prestige expectations had a significant interactive effect on career indecisiveness. Perceived parental reward/prestige expectations were positively associated with career indecisiveness only when they perceived higher levels of parental comfort/stability expectations. For men, perceived parental comfort/stability and reward/prestige expectations had no interactive effect on career indecisiveness. We addressed the importance of joint influences of differential parental expectations on young adults' career decision-making across gender.