Remember when we were kids and we could literally spend hours scribbling across pages of paper, inventing our own creative and meaningful sigh systems to convey our personal worldview? Growing into adulthood many of us move away from imagery and begin to depend on language to express ourselves. The image is an incredibly powerful method of communication, possessing a unique ability to probe individual levels of meaning that language fails to achieve. Won't you play with me? examines how imagery can demand engagement from users, provoke, creativity and challenge how adults perceive their reality and the self through the form of an interactive book. The book uses a multitude of mediums to create a variety of activities inspired by our own forms of childhood meaning-making. Though each activity features quintessential millennial narrative, each user will engage with the content based on their own individual experiences. Through our use of interactivity, we seek to explore how collaborative content can be used to create dialogues through imagery.