In this article, the authors analyze the experiences of one participant in HOPE, a pilot program that supports teenage mothers who want to pursue a college education. Using feminist standpoint and social capital theories, the analysis explores the meaning of themes that are interwoven throughout four narratives about family, education, college/dreams, and HOPE. Some emergent themes, such as key relationships and client-centered learning environments, are well known; others, like the client’s perception of ambivalent social messages about mother-student roles and the function of mentoring in the development of critical thinking, are less recognized but essential to extending theory about academic decision making