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The purpose of this paper is to explore the role of intergenerational mentorship in the lives of young mothers, and how transformational mentorship can be used to enhance skills and promote success for Latinx pregnant and parenting youth (PPY). This qualitative study examined perspectives of mentors and mentees participating in an intergenerational mentorship program for PPY attending an alternative high school in Chicago. In particular, this study investigated how storytelling/testimonio (Bernal, Elenes, Godinez, & Villenas, 2006) was used to impart knowledge, develop strategies for survival and resistance, and build relationships among generations of Latinx mothers. This research hopes to add to the limited body of research on the role of mentorship in the lives and trajectories of young mothers.