Drawing on ethnographic data about 15 juvenile offenders, collected before and after my own pregnancy, this article shows how becoming a mother enabled me to access a previously closed-off research site while studying young male offenders on Chicago’s South Side. In this study, I introspectively reflect on the obstacles female ethnographers may encounter as they are trying to build rapport in a male-dominated setting. My narrative shows that the apprentice role, often adopted by male ethnographers of the American inner city, may be challenging for women to take on. Sexual advances and limited access to male-only spheres can significantly impede data collection. Yet, as I will demonstrate, women can alternatively rely on nonsexual, gender-specific roles, such that of a mother, not only to build rapport but also to broaden the perspective on field sites that have largely been explored from a male point of view.