This paper is a reflexive process that considers the practices of mainstream service providers that aim to support marginalized youth but unintentionally result in further oppression. To engage in this deconstructive exercise, we use a poem that was written in response to an activity done at a youth engagement workshop held in Montreal in June 2012. Coupled with existing literature and further reflections of a young person’s experiences with social service providers, we offer recommendations for meaningful and empowering ways to connect with alienated youth. These recommendations emphasize acknowledging the diversity of experiences, developing authentic relationships, and embracing the humanity that unites us all.