People in the United States are becoming increasingly isolated and separated, and this disconnection has been amplified by the use of new technologies in which face-to-face interactions and connection are becoming an anomaly (Putnam, 2000; Turkle, 2011). These changes are paralleled by marked racial and ethnic demographic shifts and increasing racial and economic re-segregation nationwide (Passel & Cohn, 2008). A critical challenge facing higher education is fostering educational opportunities for college students to interact, connect with, and learn from diverse peers about issues of social identity, difference, and inequality, while imagining possibilities for socially-just action (Gurin, 1999; Tatum, 2007). This qualitative study explores the role of personal storytelling about social identity-based experiences in two undergraduate diversity courses informed by social justice education pedagogies with a focus on race/ethnicity and racism. Three bodies of literature inform this study: storytelling, social justice education, and personal storytelling in social justice education practice. Using grounded theory (Charmaz, 2006), the researcher analyzed secondary data sources from 32 participants in two undergraduate diversity courses at two Northeast universities. Study A examined final papers from a racially diverse group of 16 students in a social diversity and oppression course. Study B examined interviews with a racially diverse group of participants in two race/ethnicity intergroup dialogue courses. Findings suggest that listening to personal stories about social identity-related experiences is a powerful accelerator of learning about social justice issues and demonstrates that students across identities value storytelling, describing it as engaging, enjoyable, and integral to their learning. Storytelling fosters connection among students and encourages empathy within social groups and across social group differences. Listening to stories allows students to connect to the course material cognitively and affectively and helps information become “real” to participants. This connection facilitates critical thinking and a host of learning outcomes. Findings build on existing knowledge illustrating the benefits of diversity and intergroup dialogue courses (Bowman, 2011; Gurin, 1999; Gurin, Nagda, & Zúñiga, 2013), underscoring the value and impact of face-to-face, synchronous learning as a valid, transformative, and critical educational method in diversity courses. Additional implications, limitations, and suggestions for future research are also discussed.