Decades of research makes clear that people’s cultural background and group identity make a substantial impact on their empathic responsiveness. Our current understanding of empathic perceptions and reactions in a group of people, called biculturals, is limited. The majority of the research is correlational focusing on the connection between a set of limited factors and empathy. Moreover, there is growing evidence showing that being “bicultural” is more than having a set of correlational factors. This study argues that the concept of “bicultural” should be addressed as a naturalistic phenomenon requiring naturalistic experiments to have a more comprehensive understanding of the underlying factors. Accordingly, researching on psychological concepts such as empathy among biculturals would be a naturalistic experiment that allows researchers to test different theories regarding the studied phenomenon. This study used a mixed-method research design approach with a greater emphasis on quantitative strands. To address the purpose of this study, participants’ dispositional empathy as well as cultural orientation and sensitivity toward other cultures was measured through self-reported questionnaires. Drawing from the existing studies on the interplay between culture and empathy (e.g., Cheon et al., 2011; Yoon, 2014), participants’ empathic reactions toward observing an individual in painful and non-painful situations from ingroup and outgroup cultures was also explored. Additionally, this study explored how Americans and Iranians, two nations that have been represented as threat by their respective governments, viewed each other with a particular focus on the most dramatic incidents in the political relationships between these countries (Shahghasemi, 2017). Findings from the present study suggest that cultural orientation significantly affects empathic responsiveness. However, the relationship is dependent on the component of culture as well as on different components of empathy in different settings. Moreover, unlike their government and previous studies (Gerges, 1997), both nations had a positive viewpoint about each other and did not perceive each other as enemies. There was no sign of schadenfreude, the opposite of empathy (Cikara, Bruneau & Saxe, 2011), as all participants believed the two incidents should have not happened and they tried to be empathic toward observing other people in pain regardless of the person’s nationality. It seems the new generations in both populations, are developing their own viewpoint in which they try not to mirror the image created by their government (Johnston Conover, Mingst, & Sigelman, 1980).