Despite dramatic increases in the Latina/o population represented in US schools and disparate representations of youth mothers across racial/ethnic groupings, Puerto Rican and Dominican youth mothers remain peripheral to educational policy investigations. This book critically examines the ways Puerto Rican and Dominican youth mothers negotiate macrolevel policies surrounding teen pregnancy and sexuality education across local, urban school structures. Through feminist critical policy analysis and Latina feminisms the author reveals ways in which Latina youth mothers are constructing (im)possible selves across academic and guidance counseling structures and an on-site parenting youth program. Youth negotiations highlight implications surrounding policy initiatives for youth, improving school practices and programs, reconceptualizing curriculum surrounding teen pregnancy and sexuality education, and fostering culturally responsive teaching. This work is particularly relevant to educational researchers, K-12 school officials, teacher educators, and policy makers.