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This chapter explores mentoring and mentored learning in pre-service education at the encounter between two cultures (Arab-Druze student teachers and Jewish mentor teachers). Drawing on an illustrative case study from a larger data set of mentoring conversations and open-ended interviews in a study of intercultural mentoring, we propose an analytical framework for examining complexities within mentoring relationships that considers the social and cultural values, forms of communication, and reasoning and behavior of mentors and student teachers that may remain latent and unacknowledged. The discussion invites teacher educators, curriculum developers, and policy makers to consider how to support the development of mentors as culturally sensitive and responsive professionals.