Although research has described mentoring programs to have positive effects with youth, there are few studies that describe how mentors build relationships with homeless youth. In this study, I sought to explore how mentors of a community-based organization, Starting Right Now, built relationships with homeless youth. Starting Right Now is a multi-faceted, community-based intervention developed in 2009 in Tampa, FL. They provide services to homeless adolescents who are no longer living in the custody of a parent or guardian. The program provides residential, educational, recreational, and professional development services, as well as mental and physical health care. Additionally each youth in the program receives a trained mentor. A qualitative approach allowed mentors to share what strategies they used to connect with their mentee and overcome challenges within the relationship. Five female adults were recruited from Starting Right Now to participate in individual semi-structured interviews. Results showed that for some mentor-mentee pairs, the relationship developed easily if they found similar commonalities (e.g. outgoing personalities). Further, mentors discussed the strategies and activities that created a closer relationship and how they overcame challenges with the relationship. Finally mentors discussed the advice they would give to someone else looking to mentor a homeless youth. Overall mentors in this study reported that commitment and patience are major components to being a successful mentor to a homeless youth.