The Youth Leadership Council supported by the Illinois Caucus for Adolescent Health completed a Community-Based Participatory Research study to assess the perceived barriers and benefits to conversations about sex and sexuality between youth and their given and chosen families. This mixed-methods research project defines given families as the family youths are born into or live at home with, and chosen families as those youths choose to surround themselves with such as friends or mentors. The Youth Leadership Council found that youths discuss sex and sexuality with both given and chosen families, but a majority felt that they received only “somewhat accurate” information. This project builds on current and past research by allowing youths to disclose their gender identity and sexual orientation, which showed a clear need for more education around asexual identities especially within given family settings. As a Community Based Participatory Research study, pragmatic next steps based on the finding are included for practitioners and researchers who work in the area of adolescent sexual and reproductive health.