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This paper discusses some ways educators may utilize their knowledge of generational characteristics and differences to enhance their teaching and inter-generational relationships with Millennials. It cautions against over- generalizing the popularly accepted generational characteristics to diverse students; it suggests that, like any other category of social classification, generational difference should be considered within the larger context of social diversity, including race, class, and gender,and geographical region. This paper critically discusses specific strategies that educators, who are working outside their comfort zones, can employ to increase the effectiveness of the educational experiences they facilitate for diverse millennial students.