This article examines the hermeneutic, narrative, and social co-construction of cultural understanding as two educators shared their teaching and learning experiences in Japanese and Canadian schools. Our dialogic inquiry reveals how perceptions of practices in one culture--including curricula in non-core, academic subjects, stances on student assessment, and attitudes toward extracurricular activities--were shaped by our prior school experiences. The study reveals that reconstruction of previous overseas experience and co-construction of meaning from this reconstruction can serve as a powerful means of enhancing understanding of cross-cultural issues. The reconstruction process also offers a means of engaging those who do not have international, educational experiences in discussion of these issues. The article concludes that seemingly casual, everyday conversations can offer insights that inform teacher practice as well as preservice teacher education.