This case study relates experiences and candid reflections of front-line staff in the STAND program (Street Trade Alternatives and New Directions) providing outreach to young sex trade workers in downtown Toronto. The authors describe how this project came to be and the lessons learned in setting it up and providing services to this vulnerable, very hard to reach but resilient population. Through a sharing of tales and narratives of outreach, the authors corroborate some of the reasons why there is much written on outreach but little specifically about reaching out to sex trade workers. The traditional response and approach in working with children and youth is also questioned in the light of negotiating power, building relationships, and actively waiting for the client to lead the change process.