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Given the critical significance of empirical studies of diversity, it is important for researchers and assessment practitioners to gain insight into how students are interpreting and answering survey items that have noteworthy implications for policy and practice. To examine how students make meaning of survey items related to diversity, we interviewed a racially diverse sample of 31 students at a Mid-Atlantic university about their experience taking a short survey on cross-racial interaction and engagement with racial diversity. Survey questions came from a national survey of college students that has been used in numerous influential studies. Interview questions focused on students’ experiences answering items related to cross-racial interaction. We identified 5 themes from participants’ responses: hesitancy or uncertainty on linkages to race, straightforward answers, influences from diverse contexts, reflections on question–respondent fit, and questions on the nature of interactions. We gained various insights and recognized nuances related to cross-racial interaction and campus diversity highlighting the complexity and lack of standardization in how individuals interpret survey questions.