We present findings from a field study of Wayve, a situated messaging device for the home that incorporates handwriting and photography. Wayve was used by 24 households (some of whom were existing social networks of family and friends) over a three-month period. We consider the various types of playfulness that emerged during the study, both through the sending of Wayve messages and through the local display of photos and notes. The findings are explored in the context of the literature on play, with the aim of identifying aspects of Wayve’s design, as well as the context in which it was used, that engendered playfulness. We also highlight the role of play in social relationships, before concluding with design implications.