This paper examines how pre-service teachers were able to explore their own beliefs and build meaningful relationships with elementary school students in an after-school context. After school programs provide an opportunity for teachers and students to get to know one another in a way that is not typically possible during the regular school day. Through observations and review of pre-service teacher journals, insights about the value of after-school programs as a sight for self-appraisal, challenging biases, and confirming (or reconsidering) the choice to become a teacher are revealed. Results suggest that combining the after-school practicum experience with selective readings and class discussions allowed preservice teachers to take a critical look at their choice to become a teacher and their disposition toward typically marginalized children and schools.