This paper explores the possibilities of using character education through poetry to cultivate virtue in a secondary-school context. It focuses on the philosophical assumptions behind the intervention development and some implications of the intervention. We explore character education and poetry teaching as a tool for moral reasoning through the means of the method of 'poetic inquiry,' drawing also on insights from Wittgenstein. Character education and 'poetic inquiry' share similar goals, but are not harmonious as far as theory and methodology goes. It clearly matters what exactly is to be cultivated, and in this paper we show that 'poetic inquiry' and character education, if used to foster practical reasoning, can be used as a means of ethical-cum-emotional self-cultivation. What makes both these case-specific approaches effective, and to some extent unique, is the possible employment of creative writing, and the development of the intellectual virtue of creative critical thinking.