This dissertation offers a longitudinal in-depth view into how students respond to a structurally diverse campus, a series of hate crimes and incidents of racial discrimination and bias, and a distinct set of creative engagement diversity activities. With a focus on racial and political identity differences, I employ social identity theory and symbolic interactionism to look at how these three aspects shape their social identities, their opinions of diverse others, and their opinions of diversity in general during their undergraduate career. To explore this, I engage members of the 2015 incoming freshman class and then analyze results from three data sources administered to them: a four-year online survey (n=170), a paper questionnaire (n=537), and two sets of in-depth interviews (n=62). My findings run counter to those of Pettigrew with and Tropp and others (2015, 2011, 2000, 2006): for this cohort intergroup contact does not reduce prejudice. Students in this study are on the leading end of Generation Z, which looks to be the most accepting of diverse others generation to date. Although this cohort and this campus satisfy Allport’s (1954) conditions for prejudice reduction, this does not occur based on my data. Further, a series of distinct creative engagement diversity training activities has no long-term positive effect on their opinions of diversity and diverse others. Diversity and inclusion endeavors without multifaceted, dedicated efforts do not necessarily lead to positive changes in students' attitudes, identities, behaviors, and experiences. This research holds potential to contribute to the canon of social psychology and diversity training practices.