The questions of an inquiry sometimes feel ephemeral; evolving into presence, sometimes departing while at other times lingering within the contemplative transit. Their ephemeral nature in turn sustaining the life of the “perpetual seeker” (Miller, 2016, p. 138); and underscoring how the terrain of contemplative inquiry is a paradoxical place. Its crossing marked by transitory presences but also another wherein questions emerge and elect to remain with us. Chapter 3 attempts to corral such transience within an overview of questions into the relation of wisdom and art which emerged during the journey of my project and are of two broad configurations. The first are ones about the relation of wisdom and art that were sparked by a synchronous reading of three texts: John P. Miller’s Educating for Wisdom and Compassion (2006); Ferrari’s & Potworowski’s Teaching for Wisdom (2008); and Thomas Merton’s Love and Living (1979). Pondering these texts in tandem with Merton’s other aesthetical writings and his strategy of direct engaging with the reader which is found in some of his texts, formed the second set of questions. The latter touch on methodological questions for an arts-enriched contemplative inquiry; and are explored through kindred explorations of dialogical discourse in the work of Hart (2004) and Palmer (1993); and Gunnlaugson’s thesis of “generative dialogue” (Gunnlaugson, 2007, p. 138). The chapter is underscored by the thesis that while the journey of questions is immersed within a ceaseless transit, the seeking of certainty is not its primary goal (Hart, 2009). Instead, as Tobin Hart following the physicist David Bohm observes, the promise of wonder is nurtured when the goal of certainty is abandoned.