This chapter offers a glimpse into an atypical genre of single-parent family in Japan – a view from the perspective of a single non-Japanese father with young bicultural children. Interactions between the family members and systems of education in Japan can shed new light on cultural gender-based biases and traditionally held stereotypes. The confluence of connections between individual participants, gender role expectations, dominant cultures, and education, are explored in this study through autoethnographic methodology (Ellis et al., 2011; Strauss & Corbin, 1998) and the process of organizational sensemaking-the process by which people give meaning to their collective experiences (Weick, 1995; Weick, Sutcliffe, & Obstfeld, 2005). Educational settings bring together Japan's diversity within one setting, making intercultural encounters routine. Situations where there are perceived microaggressions (Pierce, 1970), cultural bumps (Archer, 1986), as well as examples of ethnocentrism and ethnorelativism (Bennett, M. J., 1998b) are examined and discussed within cultural, gender, and dominant culture privilege (Kimmel & Ferber, 2016; McIntosh, 2003) frameworks. I will make a case that intercultural sensitivity (Bennett, M.J., 1998a), as well as shifting into other perspectives or worldviews, can lead to enhanced intercultural understanding resulting in win-win outcomes. I will make a second case that autoethnography and organizational sensemaking are particularly well-suited methods for initial inquiry into fringe cultures, such as non-Japanese single fathers raising bicultural children.