Adolescence is a developmental process with multiple psychosocial dimensions and the social meanings attributed to it place youth in a social limbo; they are not children but not yet adults. It is important to contextualize the difficulties gay adolescents face due to their sexual identity, their social vulnerability associated to their particular developmental process, and their ethnicity. We explore the vulnerabilities and strengths of a sample of Puerto Rican gay and bisexual (GB) male youth. Participants were 61 highly educated GB youths living in Puerto Rico. Levels of depression, perceived social support, alcohol and drug use, and sexual behavior were assessed. Results show that 45% of participants reported high levels of depression. However participants reported low levels of alcohol and drug consumption, no unprotected sexual behavior, and high satisfaction with social support. Participants showed a high level of resilience associated to their social networks, consistent use of protection for high-risk sexual behavior, and capacity to integrate their sexual orientation to their overall development in a heterosexist Latino society. Although results cannot be generalized to all Puerto Rican GB youth, they are useful to support the need for community level interventions addressing the strengths of this population.