The most challenging youth have learned to be experts at outwitting helping professionals. Often with hurt kids, if interactions move beyond the stuff plainly spoken and capture the emotional nuance, the student will respond with an amplification of his emotional tone. Hurt, abandonment and rejection make this student adult wary and impact his interactions with anyone perceived as a threat in his space. His expectations of strangers outside his circle have been imprinted by past hurt, abandonments, and rejections, and in this case, past abuse. His expectations are for more of the same unless he protects himself. The skill of listening is a complex, multidimensional skill that requires listening with the ears, the eyes and the heart in order to really understand the important communication of young people. Kid Whispering requires the skill and sensitivity to give significance to what the young people say in the context of the way they say it and the circumstances from which the words come. Kid Whisperers are able to respond to the offensive and defensive language of youth while looking for meaning in their non-verbal communication and their needs. This article demonstrates the process of reconnecting with adult-wary kids. (Contains 1 figure.)