Phenomenology, peekaboo, and play are notions that may not tempt the reader to take a paper very seriously. Phenomenology is a philosophical form of qualitative research that is guided more often by the fortuitous serendipity of contemplative insights than by the rationality of reproducible social science procedures. Peekaboo is an infant game of the eyes that hardly seems worth addressing in a self-respectful research journal, and the topic of play is equally suspect to scientists for whom the cheerful idleness of play is the opposite of the seriousness and purposiveness of work or labor. However, here I will propose that (a) peekaboo may give us inceptual insights into the phenomenon of eye contact; (b) idle play is not just a counter concept of seriousness and work, but a phenomenon in its own right; (3) phenomenology is a serendipitous form of research that is philosophic and may give us compelling insights into the lived meanings of quotidian experiences in our lives, and (d) the mythological figure of Kairos speaks to the enigma of our humanness and provides an understanding of time as the discontinuous instant of the now and of the phenomenological method as intuitive grasping of meaning. Phenomenological writing is rarely easy and yet it can be highly satisfying in its results. I aim to show that meaningful insights are gained through a patient and attentively alert surrender to Kairos time and serendipitous moments. © The Author(s) 2018.