How do the choices we make affect the people we love? Gwen Haworth, filmmaker and subject of this smart and well-crafted documentary, examines her own gender transformation - from self-realization, and repression, to acceptance and surgery - through interviews with the six closest people in her life - her parents, two sisters, best friend and wife. Blending humor with frank emotion, She's a Boy I Knew is an intimate self-reflexive journey through the eyes of others.