Emotional pain which manifests itself in problem behaviours is, for many children and youth, a part of their everyday struggle through life. Kids growing up in residential care or in a dysfunctional family or setting suffer this pain. Connecting with kids in pain, the primary task for youth workers, is made all the more difficult, the greater the pain that the young person experiences. Connecting with these kids requires understanding their humour and the reasons they may appear to use inappropriate humour to make connection more difficult. It is important to be able to distinguish when they are using humour to increase their pleasure and when they are using humour to avoid potential pain. For a positive connection to occur, an adult must attend to four important aspects of relationship: (1) trust; (2) respect; (3) understanding; and (4) empowerment. As humour often involves laughter, the author stresses that young people who are used to being treated as objects may assume the worst. Laughter in working with young people, as with most aspects of humour, can be very useful and therapeutic. However, if not read correctly by the youth, laughter can undermine and seriously damage relationships. In this article, the author discusses the role of humour in connecting with kids in pain and how it can bring about connection through induction of pleasure.