In an article recently published in the Journal of Early Childhood Research, two student researchers and I described a study that we conducted in 2014 of how preschool-aged children’s ability to play four types of verbal games might be related to their broader language and social development. The study was small scale with a sample of only 25, but took many months of planning and resulted in an innovative new way of thinking about the “silly” word games children play. This case study provides an account of some of the theoretical and practical challenges of defining and measuring a construct like play and designing an age-appropriate study to elicit types of play in a preschool classroom, as well as some of the surprising discoveries we made in the process. The case illuminates issues relevant for working with young children in an educational setting, and specifically when trying to organize and measure behaviors that usually occur in a spontaneous and natural way without compromising ecological validity. Understanding the pros and cons of the choices that we made throughout this research process will help the reader become more aware of what goes into making objective numerical measures of natural messy human behavior.