This qualitative study focused on the stories told by five, White, female teachers with a long-term commitment to teach at a predominantly Hispanic high school. The stories of these teachers' life experiences were part of a teaching journey that began long before their formal teacher preparation. Understanding the personal, practical knowledge embedded in the events and experiences of these teachers' journeys was important to study, as these teachers possessed an extremely positive personal and academic reputation with their mostly Hispanic students. This study shed light on possible reasons for these teachers' longetivity in the profession of teaching as well as their ability to bridge cultural differences potentially dividing them from their students.Data collection came from classroom observations, a questionnaire, and a series of three, semi-structured interviews. In a cross-case analysis of the narratives compiled from the data, three main types of stories were told: stories of cross-cultural experiences, difficult challenges, and conversations with students. The highs and lows of these unusual women's experiences provide cases for preservice teachers to consider as they prepare to teach an increasingly diverse student population. These cases also reinforce the importance of cross-cultural experiences and intimate knowledge of challenging issues facing Hispanic communities as a prerequisite both before and throughout teacher preparation programs. These cases also emphasize the importance of conversation as a cultural strategy in bridging the cultural divide with Hispanic students.