In the summer of 2007, I observed a leadership camp in Virginia that was held by Iranian Alliances Across Borders (IAAB) , a small grassroots organization for the Iranian-American community, empowering immigrant adolescents as future leaders in the United States. The summer camp employed Freirean pedagogy and theater techniques by Augusta Boal’s Theater of the Oppressed (1979) to practice dialog, build connections, and encourage the young participants to overcome the oppression they feel as immigrants. Observing such practices introduced me to Freirean practices and pedagogy. After reviewing Freire’s work I learned about his liberatory pedagogy of education, concept of dialog, and how this pedagogy tackles oppression by suggesting problem-posing and bottom-up strategies of knowledge making instead of authoritarian banking education. Inspired by the positive impacts of Freirean projects in different regions around the world, I went to Tehran, Iran in the summer of 2008 and conducted a one-week Freirean summer camp in collaboration with a team of Iranian and Iranian-American practitioners in order to create a liberatory space for adolescent girls to practice expression skills. Bartlett (2005) identifies that “understanding the meaning of dialog” and “transforming traditional teacher-student relations” (p. 345) are among the most challenging aspects of Freirean pedagogy for practitioners around the world. Examining Freirean approach in theory and practice, I use Bartlett’s (2005) study as a heuristic framework for the current study to portray how the practitioners in the summer camp understood the key concepts of Freirean pedagogy. In this study, I used portraiture methodology to draw a picture of the practitioners’ understanding and employment of Freirean pedagogy. Portraiture is a qualitative narrative inquiry methodology that paints individuals and their detailed and complex socio-historical contexts with words. Painting with participants’ words, the current study portrays how sociopolitical complexities of the society influence practitioners’ understanding and employing of a democratic pedagogy in theory and practice.