The relationship between teacher and student is instrumental to learning (Davenport & Davenport, 1985; Holmes & Abington-Cooper, 2000; Houle, 1996; Knowles, 1980; Knowles et al., 1998; McGrath, 2009). This essential partnership supports instruction and student achievement (Bernstein-Yamashiro & Noam, 2013; Hen & Goroshit, 2016; Marzano, Frontier, & Livingston, 2011; Spilt et al., 2011). Moreover, considerable research suggests that individuals learn more effectively from an experiential education (Dewey, 1966; Knowles, 1970, 1980; Knowles et al., 1998; Littky, 2004; Washor & Mojkowski, 2013). One population already engaged in project-based learning includes students at Big Picture Learning high schools. While much has been studied regarding how students engage in project-based learning, there is less known about the role advisors play in the way a student assumes increasing responsibility for their learning. Thus, the purpose of this qualitative phenomenological study was to explore the contribution of the student-advisor relationship in the progression of student learning, guided by the following research question: What role does the student-advisor relationship play in the transformative journey of a Big Picture Learning high school student? Using a phenomenological hermeneutic approach (van Manen, 1990, 2015), purposefully selected former high school students (N = 6) and their advisors (N = 6) were interviewed. Pivotal student documents (N = 12) were analyzed, and elite interviews (N = 2); the co-founders of Big Picture Learning contextualized the primary interview findings. Data were analyzed using a within-case and across-case strategy to identify patterns and themes (Lincoln & Guba, 1985).Findings indicate that belongingness, culturally responsive teaching, and social-emotional competency facilitate a secure student-advisor relationship (Bowlby, 1988). This relationship supports an andragogical learning environment (Knowles, 1980) where students become self-directed and engage in critical reflection (Mezirow, 1991), supporting transformative learning. Educators interested in student-advisor relationships effectively supporting high school learners in their educational journey may find value in this study. The findings may also help leaders identify ways to support relationship-building practices, with targeted professional development, hiring, and onboarding processes for new teachers. Furthermore, this study provides a foundation for future exploration regarding the student-advisor role in the transformative learning journey. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]