Using the experiences of Andy, a working class adolescent exploring his gay identity, and the dialogical and transactional relationship he developed with Kristi, his senior-year English teacher, we argue that the teaching of reading and writing must be seen as more than the learning of discrete skills to enable future employment. On the contrary, all transactions with texts should be viewed as providing learners with a range of ways to scrutinize their lives and the lives of others. We suggest that by taking a transactional and dialogical stance on the teaching of English, teachers and learners become inquirers into and ongoing co-constructors of their individual and collective selves. Through dialogue with others, they simultaneously dialogue with themselves, becoming agents in the continuing formation of their many cultural lives. Specifically, we use the experiences described herein to show the unique and necessary presence of dialogical transactions in the lives of Andy and Kristi and the range of possibility and consequence these transactions provoked.