Previous studies on self-enhancement bias used self-report measures to investigate individual and cultural differences in well-being. In the current research, we took a behavioral approach to analyze positive and negative perception tendencies between European Canadians, Asian Canadians and Koreans. In Study 1 and 2, participants were asked to bet on their expectation of success on a given task and then perform the task. The betting behaviors and actual performance were used to quantify positive and negative perception tendencies. In Study 1, we did not find cultural differences in positive and negative illusions. Positive self-perceptions were also not associated with higher self-reported well-being. In Study 2, we employed the same research design as Study 1, and we included a measure of perceived desirability to examine whether perceived desirability of the performance tasks are related to the two illusions indices. The results from Study 2 replicated the findings from Study 1, and perceived desirability did not influence the results. Our findings suggest that North Americans do not always exhibit more positive self-perceptions than Asians, suggesting that North Americans do not always view the self through rose-colored lenses.