Young men who have sex with men have the highest rates of new HIV infections in the U.S., but they have been understudied relative to other populations. As a formative step for the development of a text messaging HIV prevention intervention, this mixed methods study aimed to understand how adolescent gay and bisexual males (AGBM) make decisions about condom use and factors that may differ based on age, sexual experience, and rural versus urban residency. Four online, asynchronous focus groups were conducted with 75 14-18 year old AGBM across the U.S. Qualitative analyses uncovered themes related to relationship influences on condom use (e.g. marriage, trust), access issues, and attitudes and experiences that both encouraged as well as discouraged condom use. Mixed methods analyses explored differences between groups in endorsement of themes. For example, younger and sexually experienced participants were more likely to report the cost of condoms was prohibitive and sexually experienced and rural youth were more likely to describe being influenced by emotional aspects of the relationship. These data highlight both opportunities for as well as the importance of tailoring HIV prevention programs for sub-groups of AGBM.