Although there is a realization in Western society today that childhood is changing, the topic remains clouded in confusion and contradictory viewpoints. The central question, if and how the nature of childhood itself has changed, has led the author to conduct a metabletic inquiry. Metabletics or the science of change is a human science research approach that incorporates phenomenological methods and seeks to understand a phenomenon by taking its historical development, its social cultural context and relevant synchronistic developments into account. In exploring the changing nature of childhood, historical, metabletic, and phenomenological studies were consulted as well as some selected sources from literature, art, and entertainment that portray the lives of children and, in particular, of boys in the past and in the present. First, a brief historical perspective on the changing nature of childhood from traditional to modern times is presented. This is followed by the concept of modern childhood and its transition to a postmodern childhood. The author aims to describe the essential characteristics of childhood with a focus on boyhood as lived in different historical time periods in order to contribute to a clearer understanding of its changing nature. The present study is exploratory and opens a vast domain that awaits further detailed investigations.