American Indian youth experience teen birth and school dropout at higher rates than other racial and ethnic groups in the United States. Early childbearing is associated with adverse health and socioeconomic outcomes, including attenuated education. However, kinship childrearing norms among Northern Plains tribes can support positive experiences of early childbearing. Using a community based participatory research framework, this mixed methods exploratory study engaged high school students from a Northern Plains reservation community to examine youth perceptions of family support and belief in ability to stay in school should they have a child. We elicited youth observations of facilitators and inhibitors to academic achievement for young parents. This research supports the need for strengths-based, gender specific, and family inclusive sexuality education to support young people in their reproductive choices in reservation settings. We highlight the utility of including youth as coauthors and co-researchers in future studies.