This thesis examines how different types of connection – intimacy, community, and compassion – can positively impact the cultivation of well-being and ways of knowing. Using Scholarly Personal Narrative methodology (narrative storytelling supported by scholarship) I describe my journey from the 15-years I lived as a monastic yogic nun, followed by a period of heartbreak, to my recent experience as a tip-toeing Buddhist and mid-life graduate student who yearned for community, a place to belong, and an opportunity to be heard, seen and valued. I explore how the pain and suffering of loneliness, grief, loss, and change, when met by presence, patience, awareness, care and flexibility, can help to strengthen one's relationships with the self, others and surrounding environment. I close by outlining how contemplative pedagogy (learner-oriented, introspective and experiential learning) can help to create new ways of knowing, improve cognitive functioning and well-being, and cultivate compassion. I demonstrate how these three connections can transform the higher education learning experience from an abstract, impersonal view of reality to an authentic, interconnected, and intimate one that help students develop long-lasting and meaningful relationships well beyond the classroom walls.