This essay draws lessons from implementing a new Freshman English curriculum in a Middle Eastern university. Three inter-related areas of emphasis are outlined: 1). Universities as a rite of passage; 2). Auto-ethnographies as an effective means for students to reflect critically about and narrate their own coming-of-age process (or movement between worlds); 3). Stories from Coming of Age around the World were used to model relevant themes in the coming of age process, such as diversity and gender. These included stories from the Middle East and the Caribbean, such as “The Veil,” “The Women's Swimming Pool,” “Shoes for the Rest of My Life,” and “Man-Self.” Here I will concentrate on two stories in which gender roles and the rewriting of scripts are foregrounded (“Man-Self” and “Shoes for the Rest of My Life”). A subsequent paper will develop a comparative perspective on teaching two stories set in the Middle East (“The Veil” and “The Women's Swimming Pool”).