Despite ongoing prevention efforts, young gay and bisexual men (YGBM) accounted for more than three fourths of all recent HIV infections. Furthermore, they continue to engage in high-risk sexual behaviors at alarming rates. Nowadays, families are beginning to emerge as important resources for these youth. However, the viewpoints of YGBM and their families are largely missing from HIV prevention research and intervention development. To address this gap, we solicited the opinions of YGBM and their parents as to why YGBM engage in unsafe sex and what might be done to help them avoid HIV. Participants discussed youth’s sense of invulnerability, sexual arousal, parental disapproval, and lack of societal acceptance as contributors to unsafe sex. Participants called for gay-sensitive sex education and community programming as well as increased societal acceptance. Overall, respondents recommended interpersonal and structural-level interventions that emphasized the importance of reducing stigma as a key component of HIV prevention.