This article explores how a Chicana/Mexicana teen parenting educator along the U.S./Mexico border crafted her pedagogy from personalized care, conceptualized as "borderland pedagogies of cariño" (care). This approach is rooted through the teacher's interactions with teen mothers who straddle contradictory identities like the boundary of mother/student. Classroom interactions were analyzed through narrative inquiry to understand the pedagogical orientation of the teacher--in effect generating theory from practice. One narrative is featured to show how "cariño" results in an overall transformation in classroom interaction that leads to student engagement and teacher fulfillment.