Cross-cultural mentoring relationships between younger mentors and older mentees are increasing in frequency across all levels of post-secondary education. Generational cultural differences can result in conflict and misunderstanding and therefore should be considered in non-traditional inter-generational mentoring relationships. Through auto-ethnographic inquiry, we, a younger faculty member and older graduate student, explored our mentoring relationship. We identified communication, respect, and ambiguous roles as issues that significantly impacted our mentorship. The manifestation of power was also highlighted in the study.