Despite research in the topics of identity and self, the construction of the self continues to be a problem in social science research, as the details of this process have remained mysterious (Miller, Fung, & Koven, 2007). This study explored the caregiver-child relationship and the way in which a child's self is negotiated through interaction with a caregiver in a foster home setting, using an analysis of discourse of naturally occurring data collected over four months. Three discourse genres emerged, "boys to men," "you're bad," and "learn the hard way." The "boys to men" genre highlights the culturally defined identity of "manhood." The "you're bad" genre shows how a "bad" identity is imposed on and refuted by one foster youth. I introduce the concept of a "trajectory of self," which serves as the end point or the telos toward which each participant strives or upon which others are measured. The "learn the hard way" discourse highlights how one familial discourse of a socially acceptable self (e.g., good student) functions as the rubric by which the foster child is measured despite having a different measure of his own (e.g., good athlete). Through this process of contextualization, whereby the foster family identified the child as being a person of a certain sort and interpreted his actions as being illustrative of such, he was positioned accordingly along the familial trajectory of self until an empirically observable self emerged that legitimized the familial perception of a socially acceptable self.