This article focuses on the ways young women volunteers build empowering connections with sixth grade girls in the context of a girl empowerment mentoring program. Gloria Anzaldúa’s concept of “Borderlands” is applied as a theoretical metaphor for understanding how empowering mentoring connections are made in the face of binary positionings. Narrative analysis that focus on the rhetorical properties of stories reveal the significance of three key practices including resisting role modeling, knowing how to talk with girls, and seeing difference that enable connections in the face of borders that often seem impermeable. I offer a model of creating connections that explains how volunteer actions deconstruct the borders that exist between girls and volunteers as well as shows the paths to connection and disconnection. Theoretically, insights gained from this analysis call into question theories of girlhood and adolescence that are rigid and fixed and reinforce the idea that mentoring as a Borderland experience is inherently political. Practically, this work demonstrates what works well in building connections with adolescent girls and offers suggestions about how mentoring and girl empowerment programs can build on volunteer knowledge and experience.