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The focus of theory and research on emotion regulation has shifted from emphasizing the adaptiveness of specific regulatory strategies to flexible emotion regulation in accord to situational demands. It is important to consider the role of attitudes about emotional expression in studying the contribution of flexible emotion regulation to psychological wellbeing. To test this idea, using the process model of flexible regulation (Bonanno & Burton, 2013), this study aims to investigate the effect of ambivalence over emotional expression on expressive flexibility and psychological wellbeing. A sample of n=73 young adults (n=30 males, n=43 females) were chosen from South India to participate in two phases of the study. In phase 1, the participants responded to questionnaires that measured ambivalence over emotional expression and psychological wellbeing. In phase 2, the participants undertook the Expressive Flexibility task, in which they were instructed to up- and down- regulate their emotional facial expressions. The results of the study indicated that Ambivalence over Emotional Expression was a strong negative predictor of Expressive Flexibility and Psychological Wellbeing. Additionally, Expressive Flexibility was found to be a strong positive predictor of Psychological Wellbeing. The findings are discussed within the expressive flexibility framework. The methodological limitations and avenues for future research are also discussed.