This paper explores different facets of the character type of the fool in the book of Proverbs and looks at his primary characteristics in the context of some of the main themes of Proverbs. Particular concerns are with the difficulties of parenting a fool and the idea of life as a path full of choices, with problems with communication and with other characteristics of the fool such as not listening to others, a tendency to hasty anger, wiliness and getting into unsuitable social situations. This paper puts this discussion in the context of the wider wisdom quest and its theological themes. It ends with images of the fool from Ecclesiastes and some insights for modern application.