This article examines how "Off Centre," a play by Haresh Sharma about mental health in Singapore, first devised and produced by The Necessary Stage (TNS) in 1993, provides a valuable opportunity for audiences to encounter characters labeled "mad" or "off centre" (a colloquial term in Singapore for being mentally ill), who are often looked down upon and relegated to being "useless" in the highly efficient and success-driven urban context of Singapore. It considers how audiences are challenged to respond sensitively and dialogically through a questioning process that builds empathy for persons struggling with mental health. I argue that when "Off Centre" imbricates the audience in the inner worlds of the characters to dialogue with them, it generates a pedagogical process by creating a space where sensing, listening to and questioning what happens to these characters becomes a way of learning about their battles and beliefs.