The 1991 movie Thelma and Louise and its protagonists continue to be cultural icons for many women of all ages. With quotes, song lyrics, the metaphor of living on the edge from the film and collected wisdom from pedagogy, two religious educators reflect on their vocation and leadership in a dialogue that draws implications for the teaching ministry. The themes highlighted address friendship, the journey, risk-taking, awakening, turning points, and the choice to keep going no matter what. The authors believe that their friendship and co-creating dialogue offer their students hopeful models of leadership through their conversations about their vocations in ministry and higher education. Further, the way that they share ideas and experiences are good for their students and themselves.